Healthy software companies typically don’t suddenly eliminate one-fifth of their workforce, but monday.com is doing just that as it bets on flatter teams, AI agents, and customer implementation expertise as the winning combination in the AI era.

Monday.com co-founder and co-CEO Eran Zinman today announced the “very difficult decision” to reduce the AI work platform company’s global workforce by about 20%, or 620 people.

The move has nothing to do with increasing margins or replacing humans with AI, he insisted in his post on LinkedIn; rather, it’s a calculated decision to trim down and hone the company’s focus as AI becomes integral to day-to-day workflows.

“This is not a distress signal; it is a deliberate reset, disclosed with its price attached,” said Sanchit Vir Gogia, chief analyst at Greyhound Research. “The industry has quietly swapped the meaning of productivity, and this filing is the clearest exhibit yet.”

A ‘significant opportunity’ in technology

In a SEC filing this week, monday.com said its restructuring plan reflects the “ongoing transformation of its product, marketing, and go-to-market strategy.” The move is intended to support a “leaner, more focused operating model” as the company continues to invest in its AI-driven strategy.

Zinman noted in his post that the company has shifted to “doing the work with AI and not just managing it,” and is focused on building environments where “people and AI agents [work] together in one workspace.”

In recent months, monday.com has evolved its products, strategy, and the way it serves its customers, and Zinman contended that “the organization we built for our previous chapter is not the organization that fits the new AI era.” Monday.com needs to “execute more decisively,” take on new challenges, and quickly respond to market changes, he said.

“We have never seen such a significant opportunity in software, driven by such exciting technology,” Zinman noted. He emphasized that the reduction is not to replace people with AI, nor to improve margins; the “vast majority” of savings will be reinvested into talent, products, and AI.

The restructuring will result in a “flatter organization” with fewer management layers and smaller, more autonomous teams, and monday.com also has a new go-to-market model, Zinman explained. Customers expect “deeper implementation support” as they deploy AI, and the company will work more closely with customers, increase its on-site presence, create new roles, and “adapt many existing ones.” In its SEC filing, the company said it expects to continue hiring in “key strategic areas” throughout 2026.

Workers will be expected to work better, “not harder,” Zinman noted. He pointed to several past examples where work could have been done in a few days, but instead took many months with “multiple meetings and endless friction.”

“This wasn’t people’s fault and everyone was frustrated by this,” he said. “Our new org changes ownership to allow people to make decisions and move fast.”

A spokesperson for monday.com declined to comment further on the staff reductions.

Monday.com’s key market advantages

Monday.com certainly isn’t struggling; the company expects 19% to 20% year-over-year growth in 2026.

“Companies in that position do not restructure because they must,” Greyhound’s Gogia noted. “They restructure because they have decided to become something else.”

Melody Brue, VP and principal analyst at Moor Insights & Strategy, pointed out that organizational redesign is important for real AI transformation, but while it can signal confidence to the market, it can still be “devastating” to humans.

While the company looks as though it’s trying to do right, that ultimately remains to be seen, she said. “There are often hidden internal bruises that can surface long after layoffs.”

Monday.com’s advantage is in its “structured substrate,” Gogia noted; its boards, permissions and typed workflows give agents something firmer to act on than just documents and chat history. The company highlights its natively built agents that can be configured by any team member, as well as connectors with Claude, Microsoft Copilot, and ChatGPT, and dedicated routes for external agents to authenticate and operate.

“For some time, the sharper enterprise question has been shifting from who has an agent to who owns the governed runtime in which an agent can safely act,” he said. “Structured work is a serious claim on that runtime.”

But parts of monday.com’s agent estate remain in staged release, and its product is ultimately “mid-transition,” Gogia pointed out; its agent builder carried a beta label as recently as March,. Also, the company’s pricing model changed in May to a hybrid model charging for seats as well as mandatory AI credits. And, while its AI-powered no-code builder monday vibe passed $1 million in annual recurring revenue within two and a half months, monday.com has not released subsequent outcomes, usage volumes, or attach rates.

Further, there’s an element of “gravity” with its competitors, he observed. Asana is reorganizing teams around agents, Atlassian is wiring agents into the developer estate, and others are simply bundling them into their offerings: Microsoft is doing so across the productivity stack, and ServiceNow across enterprise operations, each with identity and procurement built in.

“Their pull is strongest exactly where monday.com wants to grow, in the largest accounts, where control-plane depth and administrative reach decide the deal,” said Gogia.

Actions for the near-term

Going forward, buyers should focus on operating risk, not headline risk, Moor’s Brue noted. In practice, that’s continuity of service, roadmap consistency, and strength of enterprise support. Productivity should be valued as better outcomes per unit of organizational effort, not mere activity.

“It should be a measure of how much smoother, faster, and more effective the operating model becomes when AI is built into the work,” said Brue.

Gogia noted that strain surfaces first in customer service, and monday.com’s attention is being redistributed. The company’s annual report disclosed that its focus is now concentrated on the largest accounts, with support for medium-sized clients moved to an AI-first and human-supported model.

During the first month of the transition, buyers should track named account continuity and escalation times, he advised. By the first quarter, keep an eye on whether credit governance and admin controls mature on schedule, and if the roadmap beyond the AI estate keeps pace. By the half-year mark, determine whether promised implementation depth is producing outcomes or “simply more billable engagement.”

Support tiers should be enumerated in writing before renewal, and buyers should contract for “side exits,” Gogia emphasized, with overage pricing fixed in advance, the right to pause consumption, and portability for workflows and agent configuration “if the relationship sours.” Finance should also insist on monthly consumption reporting by capability. Further, integration efforts, partner dependency, and change management should be considered first-class costs of the agent era, “not as afterthoughts to a license.”

“A license was a known cost,” said Gogia. “A meter is a behavior, and behavior is harder to forecast than headcount.”

This article originally appeared on CIO.com.

In public-sector and regulated-cloud work, I learned that sovereignty rarely starts as a national strategy. It starts as an auditor’s question: Who can prove where the data went, which system made the decision and what changes when the vendor or infrastructure does? That question is now moving into AI, and most sovereign-AI debates answer the wrong version of it.

They ask whether a country can build its own model on domestic data and hardware. For the United States and China, which together hold more than 90% of global AI data-center capacity, per a January 2026 Tony Blair Institute analysis, that question is worth asking. However, for almost every other government, it is the wrong place to start. The operative question is narrower: Once AI is embedded in public services, who controls the stack?

The 5 layers of public-sector control

For a CIO, sovereign AI means enforceable control across the AI lifecycle; model ownership is a separate question. Control has five layers:

• Data control: Where sensitive public data sits, and whether it can train a vendor’s model.
• Model control: Which models clear which workloads, and under what validation.
• Infrastructure control: Whether critical workloads run in approved environments.
• Operational control: Whether AI-assisted actions are logged, monitored and reversible.
• Vendor control: Whether the agency keeps portability, audit rights and a real exit.

Those five layers are the control plane for public-service AI. Floyd Dcosta recently made the enterprise case in “AI without sovereignty is just outsourced intelligence”: capability is what a tool can do; authority over how and when it does it is something a buyer can quietly lose. For public services, losing that authority plays out in the public eye.

Public-sector AI risk differs from enterprise risk. A retailer’s bad recommendation costs a sale; a government’s AI touches benefits, tax enforcement, policing and emergency response, raising the bar to due process, records retention and continuity of operations. A government that cannot reconstruct an AI-assisted decision lacks operational sovereignty, even in a domestic data center.

Evaluating risk: Concentration, jurisdiction and shadow AI

Foreign dependency is a real risk, but the exposure that matters is a sudden cutoff: A model you cannot audit, switch or exit, shut off by someone else’s order. A vendor’s nationality is a poor guide to that risk; control is.  Two markers matter. The first is concentration. In July 2024, a single faulty CrowdStrike update crashed about 8.5 million Windows machines, disrupting airlines, hospitals, banks and governments worldwide. No attacker was involved; one homogeneous dependency failed everywhere at once. The lesson points away from vendor nationality and toward uniformity as the fault line, making portability and provider diversity resilience controls.

The second is jurisdiction. In June 2025, Microsoft’s legal director for France told a Senate inquiry, under oath, that it could not guarantee that French public-sector data, even in French data centers, would be protected against US demands under the 2018 CLOUD Act. No such request had been made, and EU data has stayed in the EU since January 2025; senators called the assurance purely declarative. For the most sensitive data, residency does not equal control; the parent’s jurisdiction can matter as much as the server’s. Three US hyperscalers hold about 70% of the European cloud market, while European providers’ share fell from 29% in 2017 to roughly 15%. Concentration plus jurisdiction is the exposure a CIO must price. I have watched teams treat vendor selection as the moment risk was solved; it rarely was.

The wrong response is self-isolation. Most countries will never build frontier models, advanced chips, hyperscale clouds and talent pipelines at once; the Tony Blair Institute calls full self-sufficiency “too expensive, too slow and, for most countries, simply impossible.” The better test is workload sensitivity. Low-risk uses, such as drafting, translation and summarization, can run on commercial platforms with controls; high-risk uses, such as benefits eligibility, fraud investigation and healthcare triage, demand stricter control over data, model behavior and auditability.

Mandating domestic-only provision before a competitive option exists inverts sovereignty. Europe 2031, a five-year scenario from June 2026 by European technologists and policy researchers, illustrates the failure mode: A 2027 “buy European” mandate lands as offensive cyber capability spreads, and agencies that switched to weaker providers are locked out and paying ransoms. The scenario is fiction; the mechanism is not. Leverage comes from being indispensable, not half-hearted self-sufficiency. The closer-to-home effect is shadow AI: Mandate an inferior sanctioned tool and staff bypass it, the way shadow IT grows up around tools people find too slow. A rule that pushes sensitive work into ungoverned shadow AI reduces control instead of adding it.

Regulation and data-residency rules belong in any serious strategy, but carry failure modes. Blanket localization raises hosting costs and slows adoption without guaranteeing control, and a “sovereign cloud” on a foreign parent’s stack can amount to sovereignty theater. The more useful pattern tiers requirements by sensitivity. India’s BHASHINI shows the application layer done well: A public platform serving 100 million-plus inferences a month across 22-plus languages on a vendor- and cloud-agnostic design that keeps data and switching rights public. Sovereignty resides in the portability, not in a national model.

Building an operational sovereignty strategy

Public trust is the constraint sovereignty rhetoric tends to skip. The OECD’s 2025 review of government AI warns that opaque systems make AI-assisted decisions hard to explain and can give public servants false confidence in tools that fail quietly. State-controlled AI is the same problem from the other side: A government that deploys models against its own citizens without audit or record has gained control and lost accountability. An agency that can log, explain and reverse an AI-assisted action can defend it to citizens, courts, auditors and elected officials. If it cannot, it has bought access and called it sovereignty.

None of this is new. AI sovereignty repeats earlier fights over cloud, telecom, semiconductors and cybersecurity. Europe’s flagship cloud project, GAIA-X, became a cautionary tale; the Dutch technologist Bert Hubert called it an “expensive distraction” that produced no European cloud, the familiar result of ambition without absorptive capacity. Cloud taught governments that outsourcing infrastructure does not outsource accountability; telecom, that vendor dependency becomes strategic exposure; chips, that supply chains matter before a crisis; cybersecurity, that trust must be verified continuously. AI inherits all four at once.

Over the next five to ten years, some countries will build national platforms, more will build trusted cloud and trusted model regimes, and most will run hybrids that pair domestic data control with global model access. Trade policy will harden those choices: Export controls on compute and data-localization rules will pull the vendor market into blocs that track alliances more than open markets. For a CIO, that turns a vendor and hosting decision into a five-year bet on whose rules and supply chains will still hold. The ones that succeed will treat sovereignty as an operating requirement, backed by leverage, not a slogan. Start with the control plane before the model: Most agencies will never own the model, and the controls are what decide whether the AI they do run stays accountable. Even when procurement policy is dictated from above, these questions remain within the CIO’s authority:

1. Can we classify AI workloads by public-service risk?
2. Can we prove where sensitive data goes across training, retrieval, inference, logging and retention?
3. Can we restrict which models are approved for which data classes and functions?
4. Can we reconstruct an AI-assisted action in enough detail to explain it?
5. Can we change providers without losing continuity or institutional knowledge?
6. Can we explain the system to citizens, regulators, auditors and elected officials?

A “no” to any of these does not mean the agency lacks AI. It means the agency has access it does not yet control. Public institutions can use global innovation without surrendering public authority, but only once they know what to hold, what to rent and where dependency turns into risk.

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I haven’t slept much in the past few weeks. Not because of some theoretical cyber risk that keeps many executives awake, but because reality just delivered a real wake-up call to our industry — a call that every executive must answer, now.

Imagine this: A major global enterprise, a company most of us interact with indirectly every single day, wakes up to find its entire digital environment obliterated. Thousands of employees in dozens of offices and remote locations are suddenly offline. Customers are cut off, supply chains grind to a halt and regulators are notified with a chilling admission: “We have no idea when we’ll be back.”

This wasn’t ransomware. There was no negotiation, no decryption key to buy, no easy way out. It was destruction — deliberate, coordinated and geopolitically motivated — not monetary.

As a chief customer officer who’s worked with countless customers on cyberattack risks, my perspective hits a bit differently than a CISO or a CTO. I see the aftermath, not just the attack surface. I see the faces behind the tickets, the operations team locked out of their own systems, the support agent answering panicked calls at dawn. And I ask: How many organizations have actually stress-tested their response to this scenario — not a hypothetical, but this very real, lights-out event? Here’s what every leader needs to confront today:

Recovery is not just a technical exercise

The first assumption to break during a real crisis is the belief that recovery is purely technical.

Many organizations have done tabletop exercises and have a backup and recovery playbook, so they feel prepared. They can point to backup windows, retention schedules and immutability controls. The moment a true blackout happens, a different reality surfaces. The people who own the recovery steps either do not know each other, lack the authority to make decisions without supervisor approval or need guidance from offline systems.

The reality is that technical infrastructure almost always holds up better than human infrastructure. Organizations have built their recovery strategy around the assumption that someone competent will be awake, available and empowered when a cyber event happens.

Still, backups are only as good as their independence. Let’s be blunt: If your recovery infrastructure shares identity, authentication or network trust with your Microsoft tenant (such as Azure, Microsoft 365 or Teams), you don’t actually have a recovery plan; you have a false sense of one — and a liability. A recent survey found that while 90% of organizations express confidence in their ability to recover from a cyber incident, fewer than one in three ransomware victims fully recovered their data.

True resilience means immutable, air-gapped backups, untouchable by the same compromise. Anything less is an illusion. I talk to customers about their recovery plans constantly. The customers who have rehearsed all scenarios sleep soundly. Those who haven’t? They’re rolling the dice.

Most business continuity plans ignore ‘total blackout’

I’ve reviewed hundreds of business continuity plans. Almost all assume partial failures — a region, an application, a data center. But what if every system, in every country, goes dark simultaneously? That’s an entirely different playbook. If your team hasn’t run a drill for a global, simultaneous outage, you’re not prepared. The probability is low, but the cost of being unready is existential.

Connected devices, OT systems, field hardware, partner integrations — they all plug into your enterprise network. When the core collapses, it’s not just IT at risk. It’s operational technology, physical safety systems and in regulated sectors, potentially human lives. Understanding and testing those interdependencies is non-negotiable.

This is also where boards need to change the conversation. A study found that only 5% of companies have cybersecurity experts on their board of directors. Recovery time objectives (RTOs) should not be buried in technical appendices. It’s all jargon to boards. That makes translation essential. RTOs must be explained in terms of business impact. “We can recover in four hours” is a technical statement. “Every hour of downtime costs us $2.3M and creates regulatory exposure in three jurisdictions” is a board statement.

That is the level of clarity leaders need.

The most prepared organizations do not wait for an incident to educate the board. They bring the conversation forward proactively. They frame recovery in business terms: revenue, regulatory standing, customer trust and brand reputation.

The most effective framing is often simple. Show the most critical systems. Show what happens if each one is down for one hour, four hours, 24 hours and 72 hours. Show the current recovery capability against each and then show the gap.

If your board is not demanding real answers, your business continuity strategy is likely underfunded and your business is exposed. This is a risk conversation worth forcing because the consequences do not stay inside IT. They can show up in customer churn or missed revenue and ruin an organization’s reputation.

Threat intelligence must be actionable, not archived

Geopolitical attacks, hacktivist campaigns and nation-state targeting aren’t abstract threats. They are active risks, and that intelligence cannot languish in the security team’s inbox. Executive leadership must be looped in — and immediately — so gaps can be closed before they’re exploited. Too often, intelligence enters the security operations function and never reaches the teams responsible for recovery infrastructure or executive decision-making.

If a threat actor is targeting a specific class of backup agents, the team responsible for those agents needs to know now, not two weeks from now. If intelligence suggests destructive activity against a sector, recovery owners need to validate isolation, access paths and restoration procedures immediately. If geopolitical tension increases the likelihood of targeting, executive leadership needs to understand what exposure exists and what actions are being taken. The organizations that survive aren’t just the best at incident response. They’re the ones who anticipated, rehearsed and invested before the attack.

Part of investing in a recovery strategy requires closing the loop between signal and action. The most prepared organizations have already mapped their critical recovery dependencies to specific threat categories. When intelligence touches one of those categories, there is a named owner and a clear set of actions. No guessing or forwarding emails into the void is needed because the distance between the warning and the employees’ ability to do something is shortened.

Looking ahead, the conversation will continue to evolve beyond traditional cyber response. Because in an AI-enabled enterprise, the new question is whether the data within those systems can still be trusted. When AI systems make decisions based on enterprise data, the attack surface becomes the data’s accuracy. A threat actor who quietly corrupts a dataset over 90 days before a recovery event has done more damage than just downtime. They can poison the inputs driving decisions across the business.

Regardless of how AI will change threat intelligence and cyber response, these principles remain the same. Know your problem, whether structural or technological. Ensure your human infrastructure keeps pace with your technical infrastructure, with clear cross-functional ownership and the tools and knowledge to act autonomously. Communicate with your boards often — and correctly.

Let’s not wait for the next headline to ask, “Are we ready?” Have those conversations now. Test your assumptions. Close your gaps. Because in today’s threat landscape, resilience isn’t IT’s job — it’s everyone’s mandate.

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Cloudflare recently beat Q1 2026 earnings. Revenue up 34% year over year. EPS ahead of consensus. Full-year guidance raised. Then, in the same breath, they announced 1,100 layoffs, 20% of the company. CEO Matthew Prince’s explanation: “The way we work at Cloudflare has fundamentally changed.”

Block did the same thing. Beat guidance, raised outlook, cut 4,000+ jobs. Both framed it as architecting for the AI era.

This is not a contradiction. This is the new math boards are running. And if you’re a CIO who hasn’t started running it yourself, you’re behind.

The benchmark has moved

AI-native companies have quietly reset what “efficient” means for a technology organization. Midjourney generates over $500M in revenue with roughly 160 employees, over $3M per head. Anthropic hit a $14B annualized run rate in early 2026 with fewer than 3,000 employees. Across the top AI-native startups, the average revenue per employee is $3.48M, nearly twelve times the traditional SaaS benchmark of $300K.

Boards aren’t comparing you to your 2019 self anymore. They’re comparing you to Anthropic.

This is the pressure Cloudflare and Block are responding to. They’re not cutting people because the business is struggling. They’re cutting because investors have internalized a new denominator. Headcount is no longer a proxy for capacity; it’s a liability on the efficiency ratio.

For CIOs, this creates a hiring problem that looks nothing like the cloud or mobile talent gaps of the past decade. Those gaps were about volume: hire 100 cloud engineers, absorb the cost, build the capability… This one is about density; you’re not looking for 100 people. You’re looking for 10 who can deliver what 100 couldn’t, and justify $1M or more in value per seat.

Finding bodies to fill seats has never been easier. Finding people who operate at that level of leverage is a different problem entirely.

‘Acqui-hires’ are a shortcut with a hidden cost

Companies have figured out that recruiting AI-native talent one by one is too slow and that it’s faster to buy a team. Google’s acquisition of the Windsurf founders, Meta bringing in the Scale AI team, Accenture’s string of AI-focused acquisitions: these are acqui-hires dressed up as M&A. The premium on experienced AI talent is high enough, and the urgency real enough, that organizations are skipping traditional hiring loops entirely and buying their way in.

I’ve been on the other side of this. My company, MadKudu, was acquired by HG Insights specifically to bring AI-native capability into an established enterprise business. HG needed change agents who had already figured out how to build and ship in this new era, not just people who’d read about it. That’s the thesis behind most of these deals.

But there’s a cost that doesn’t show up in the acquisition price.

AI-native teams are fast because they operate with a different set of defaults: full access to tools, minimal governance layers, the ability to experiment and ship without a six-week approval cycle. That operating model is not a perk; it’s the fundamental mechanism. It’s why a team of 10 can do what an enterprise team of 100 can’t.

When you acqui-hire that team and then slot them into your existing approval processes, you’ve bought the people and killed the engine. The change agents you paid for become change-frustrated. The attrition that follows is expensive and predictable.

The harder realization: acquiring an AI-native team means accepting how they work. That requires deliberately carving out space for them to operate differently, not just tolerating it but institutionalizing it. The acquisition is an organizational change program, not just a hiring event.

The CIO’s real problem

The governance stack most enterprise organizations run was designed for a headcount world. Every tool vetting cycle, every vendor review, every security approval was calibrated assuming you were managing a large team where consistency and control were the primary objectives.

That calculus breaks when your goal is talent density. The same approval processes that protect against data leaks are now the reason your best people can’t do their best work. When it takes six weeks to approve a tool that your competitor’s team is already shipping with, you’ve traded velocity for the perception of safety.

The practical fix is structured experimentation: clear guardrails, defined boundaries, but explicit permission to try tools before deciding whether to roll them out broadly. Gating everything prevents you from ever discovering what 10x productivity looks like.

The skills inventory question is also more nuanced than it sounds. Job titles won’t tell you where the leverage is. You need to map the actual tasks within each function and assess which can be automated or augmented with AI. That’s where you find the people who, with the right tools, become your $1M/employee talent, not because you hired differently, but because you enabled better.

This is also where the build-versus-buy question gets genuinely tricky. As AI reshapes how products are built and delivered, your internal operating model — how you work, how fast you ship, how you use data — is becoming core IP. Outsourcing delivery means outsourcing the part of the organization where your competitive advantage is now being built.

Closing the gap without slowing down

The AI talent wars are not primarily a recruiting problem. They’re a rethinking of what organizations are supposed to look like.

Boards have a new benchmark. Cloudflare, Block, Amazon, Meta and others have already started restructuring to meet it, publicly, painfully, even while beating their numbers. The question for CIOs isn’t whether this pressure arrives; it’s whether you’re ahead of it or behind it when it does.

The organizations that navigate this well won’t win by outbidding competitors for a handful of elite engineers. They’ll win by designing operating systems that amplify the leverage of the talent they do have, by enabling their best people rather than constraining them, and by treating AI fluency as a core organizational capability rather than a niche specialization.

Talent density is the new headcount model. The sooner your governance, your tooling and your board conversations reflect that, the better positioned you’ll be when the next efficiency report lands.

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Late in a large enterprise SAP transformation, the strategic governance conversations began to drift. Instead of executive decisions, we found ourselves debating whether the program needed dedicated testing, whether cutover required a full weekend, whether twenty Agile teams really needed coordination support and whether offshore resources were adding value at all.

The questions were not coming from the delivery teams. They were coming from the executive sponsor.

The sponsor had recently been elevated into a senior leadership role and had never sponsored a technology transformation at this scale. The challenge was not authority. The sponsor had every right to ask any question they wanted. The challenge was that strategic governance had quietly turned into a debate about delivery practices, because the sponsor did not yet have the transformation context to focus the conversation anywhere else.

This is not a story about a bad sponsor. The executive in this case was a capable senior leader with strong judgment and authentic intent. They had been placed into a role they had not yet been prepared for, and the pattern that followed was structural, not personal. It is one of the more common patterns I have observed across enterprise transformation programs, and one of the most consistently misdiagnosed.

Most program failures are not execution failures. They are sponsor mismatches.

When governance becomes a debate about delivery practices

When the sponsor does not understand what an enterprise transformation actually requires, governance forums stop functioning as decision bodies and start functioning as practice debates.

You see it in the questions that get asked. Why do we need a dedicated testing phase? Can the Build timeline be compressed? Why does cutover need a full weekend? Why do we need more Scrum Masters across 20 product teams? Can the US team simply work longer hours instead of using offshore resources? On one program, the sponsor suggested shifting the entire project’s working hours to India time, despite roughly 85 percent of the delivery organization being based in the United States.

None of these questions are unreasonable in isolation. Each one targets a real cost or timeline pressure. The problem is what is missing underneath them: an understanding of the operational risks the original choices were designed to mitigate.

When sponsors ask delivery-practice questions without that context, the program leadership team ends up defending the work instead of advancing it. Decision velocity drops. Trust between the program and its sponsor erodes. Senior delivery talent disengages from governance forums where the conversation never reaches the decisions they need made. What looks from the outside like an active sponsor producing engagement is, from inside the program, an active drain on the cycles needed to deliver.

The compounding cost is not unique to any single program. PMI’s research on executive sponsorship consistently identifies sponsor engagement quality, rather than sponsor presence alone, as one of the strongest predictors of project success. The visible symptom is debate. The actual cost is unmade decisions.

Authority is rarely the issue. Literacy is

When transformations stall under a mismatched sponsor, the diagnostic instinct is to question the sponsor’s authority. Are they senior enough? Do they have the cross-functional reach? Can they unblock?

In most of the programs I have led or advised, authority was not the limiting factor. The sponsor in the SAP program above had ample authority. They could unblock any decision the program needed. What had not been developed was the transformation literacy to know which decisions mattered, which were technical noise and which were execution risks that should not be optimized away.

This is what I have come to think of as the literacy problem. Sponsors elevated into transformation roles often have deep functional expertise (finance, operations, business unit leadership) but limited exposure to the distinct functions of PMO, organizational change management, agile delivery, testing and cutover, and how each one reduces a specific category of implementation risk. They are not expected to be SAP configuration experts. But they need enough transformation literacy to recognize which questions actually belong in a steering committee.

Harvard Business Review’s research on effective executive sponsorship has emphasized that sponsorship effectiveness depends as much on judgment as on authority. Judgment is where literacy becomes operational. A sponsor with authority but limited transformation literacy will optimize for speed and cost in ways that consistently underestimate risk. A sponsor with both will make the tradeoffs the program actually needs.

Prosci’s longstanding benchmark studies on change management have ranked active and visible executive sponsorship as the single greatest contributor to change success for two decades. The word that matters in that finding is active. Active sponsorship without transformation literacy can introduce real cost. Not because the sponsor is acting against the program, but because the optimization choices they make are based on incomplete information about what the program is built to protect against.

Shift the conversation from delivery practices to business risk

When the sponsor relationship is already in place and cannot be changed, the program leadership team has one move that consistently works: shift the conversation.

On the SAP program above, we stopped explaining why the testing phase existed. We started explaining the business risk of reducing it. We stopped debating the number of Scrum Masters. We started connecting delivery capacity to coordination across more than twenty Agile teams and the business cost of losing that coordination. We reframed offshore support as a way to maintain delivery momentum around the clock rather than asking the U.S. team to sustain fifteen-hour days.

The shift is from defending delivery practice to explaining business risk. The sponsor does not need to understand why testing takes the time it does. They need to understand what the program is exposed to if testing is compressed. They do not need to know how many Scrum Masters are statistically optimal for twenty Agile teams. They need to know what coordination breaks when the number is wrong.

This reframing accomplishes two things. First, it brings the conversation back to the level at which sponsors actually make decisions: tradeoffs between business outcomes and business risks. Second, it builds transformation literacy in the sponsor over time, almost as a byproduct. By the third or fourth iteration of business-risk-framed conversations, the sponsor begins to ask the right questions on their own.

In practice, this happens through small but deliberate moves. When the sponsor asks why a phase needs the time it takes, the program lead names two or three things that could go wrong if the time is cut and what each would cost the business. When the sponsor asks why a role is needed, the program lead names the work that would not get done without it. Every delivery-practice question gets converted into a business-risk answer.

The program leadership team’s job is not to make the sponsor an expert in SAP delivery. It is to provide enough transformation context so that executive decisions reflect both business priorities and implementation realities.

There are a few phrases I have used with executive sponsors over the years that capture the underlying issue. The sharpest one:

If the decision has to go above the sponsor, they are not the sponsor.

Sponsorship is defined by what the sponsor can decide without asking someone else. That is the test. Anything else is the appearance of sponsorship, not the substance.

For CIOs supporting enterprise transformation, the implication is direct. Sponsor selection, or sponsor preparation when selection is not an option, is not a hierarchy question. It is a transformation capability question. The same execution discipline that goes into defining decision rights, structuring governance and protecting delivery momentum should apply, with equal rigor, to assessing sponsor fit and building sponsor literacy before the program begins.

A sponsor does not need to be the technical expert. They do need to know when to trust the people who are.

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Four months of Claude Code — that’s all it took for Uber to burn through its entire annual budget for AI. Token after token, engineers embraced the platform with few control mechanisms tying costs to outcomes. The result was a budget runaway and a clear case study in how limited oversight snowballs into an AI blowout.

This is a phenomenon I like to call “shadow tokens” — AI credits paid for by the company but largely invisible to decision-makers. Too many engineers have the final say over how much they consume and, therefore, what it costs. This all-you-can-eat attitude is part of the reason why Microsoft is reportedly winding down many internal licenses across key engineering teams and why one in five organizations is missing its AI spend forecast by more than 50%.

And the trend is only accelerating. By 2028, Gartner predicts that AI coding costs (driven by this kind of ungoverned consumption) will be as much per developer as the salary companies pay that person.

LLMs and agents introduce a new class of variable cost that scales with behavior rather than headcount, putting enterprises on the hook for tools that balloon with workload. I don’t see this as enterprises overspending because they’re reckless — it’s down to a lack of managerial oversight, budget alignment that demands a proven return on investment, and engineer education on how much is too much.

Going forward, CIOs need to thread the AI needle between governance that encourages transparency and reasonable spend without stifling innovation.

When shadow tokens result in real costs

The issue is that AI isn’t a traditional line item. Previously, enterprise leaders onboarded software-as-a-service (SaaS) with a good idea of the total cost. An allocated software seat or annual contract was a known quantity. The cloud added some variation (with fluctuations depending on hosting size), but instances were still modelable. AI flips this status quo on its head — the unit of consumption is behavior and the cost is exponential.

And these specifics aren’t immediately apparent at pilot. Tools can appear inexpensive in controlled experiments yet unpredictably scale depending on session length, context window size, model selection and whether agents run in parallel. This is the fallacy of the $20-per-seat enterprise plan — tokens are charged separately at API rates with no ceiling. The final dollar value of any session is set by factors that finance can’t always model in advance, particularly when these decisions usually rest with the engineers themselves.

According to Deloitte, only 21% of organizations deploying agents have a mature governance model, a real concern because they’re token-eating machines. This is what was happening at Uber — Claude Code in agentic mode was autonomously reading codebases, planning changes across dozens of files and opening pull requests. Each step quickly adds up, with Anthropic’s own documentation noting that agents consume approximately seven times as many tokens as standard sessions.

This is shadow IT and shadow AI, evolved. This time, however, many leaders approved the tool in question without guardrails governing consumption. AI hype adds fuel to the fire and normalizes long sessions. Uber’s CTO, for example, described a company-wide shift toward “agentic software engineering” with employees “who are quietly experimenting, quietly shipping and quietly pushing things forward”. This is an exciting way to test the limits of what’s possible, certainly, but it’s also a position that goes a long way to explaining how the company spent its annual AI budget by April.

Shifting the culture from usage to yield

Engineers haven’t done anything wrong here. In fact, they’re adopting and experimenting as instructed, with Uber creating leaderboards and ranking users by token consumption. More use led to a better ranking, reflecting a culture that lauds new ways of doing things. This behavior is known as “tokenmaxxing,” and its principal knock-on effect is shadow tokens — quantity-over-quality processes that leaders struggle to control until they’re fully realized in the budget. Of course, if management treats adoption metrics as performance metrics, then engineers can’t be blamed for using more tokens. The tension is that the teams driving adoption aren’t the ones managing spend.

None of this is meant to dismiss AI’s productivity possibilities and potential return on investment. Developers save 3.6 hours per week, achieve 60% higher pull request throughput and cut onboarding time in half with automation. Meanwhile, Uber shared that roughly 11% of live backend updates were written by agents with no human in the loop. However, these wins aren’t the problem — it’s that too many teams aren’t connecting input to output. I’ve spoken to admins who discovered their token spend had tripled in a single quarter after using heavier models or accidentally doubling up on agentic applications. Nobody knew until the financial damage was done.

Automation needs to happen sustainably with an eye on the bottom line. In my view, a much better metric for achieving this is AI yield — the measurable business or engineering output generated per dollar spent on tokens. Otherwise, without a feedback loop, even genuinely productive teams are flying blind.

Stopping token waste before an AI blowout

Creating that throughline between AI investment and token consumption starts with established financial metrics. This is possible via maximum spend limits (dictated by spend tagging, workload tiering and cost-per-output benchmarks) per team or project. Then, any additional allocation requires approval, closing the loop between the engineers spending the tokens and the leaders paying for them. AI isn’t cheap and teams should demonstrate a bang for their buck.

This is something we do with our engineering team at Hexnode. Resource allocation for Claude Code and Cursor is tied directly to ROI rather than letting consumption run open-ended. Given the pay-as-you-go nature of these tools, a firm usage limit per team offers simple but essential control.

Similarly, there’s room to apply some of the governance principles IT uses for device management. Things like policy enforcement, role-based access, real-time monitoring and automated alerts can flag usage behavior in advance. Uncovering such insights at the token layer works to identify power users and prevent excessive spending.

We also need to encourage cultures that praise outputs that actually achieve efficiency. AI applications that result in shipping faster, reducing rework and cutting review cycles are gains that should be celebrated. If your company hosts leaderboards, frame unnecessary token burn as wasteful rather than valuable. The organizations creating healthier consumption habits work with their engineers to understand not just how to use AI, but what responsible use looks like and what it costs.

This is a conversation teams need to have now. Anthropic just ended flat-rate pricing for programmatic workloads from June 15. Now, agents, continuous integration pipelines and automated workflows draw from a dedicated monthly credit pool billed separately from the subscription. Once that pool is exhausted, agent tasks either stop entirely or overflow to extra billing. Work can either get very expensive or grind to a halt for teams that aren’t prepared.

Getting a grip on shadow tokens means better rules and tools connecting spend to outcomes. Only by building the financial and cultural infrastructure that encourages sustainable adoption can leaders see what they’re spending, connect it to what they’re getting and course-correct before the costs become a crisis. Ultimately, shadow tokens are only invisible if we choose not to look.

This article is published as part of the Foundry Expert Contributor Network.
Want to join?

Predicting an outage is tricky business, but CIOs might want to circle Oct. 11, 2026, through Jan. 11, 2027, for likely trouble of a potentially widespread and puzzling nature.

That’s because a relatively trivial update to DNSSEC on Oct. 11, one that will take full effect by Jan. 11, is likely to deliver a series of seemingly unrelated system outages. This will come from oceans of dependencies from third-party, shadow, agentic, gen AI, SaaS, homegrown, and legacy apps — among many other quiet executable hiding spots, including virtual environments and containers.

Sai Joshitha Kathari, senior site reliability engineer at payment card giant Visa, says most enterprises have far more DNS-related exposure than they realize because of these many dependencies.

“This has the potential to create real downstream destruction when unresolved failures sit underneath important business functions,” Kathari says. 

The danger is that so many of these issues are either unknown to IT or handled by a third-party vendor and no one in IT has had reason to ask those vendors about DNS updates. 

“The risky areas are usually not the obvious managed DNS services. They are the older internal applications, hardcoded resolvers, containerized workloads, sidecar configurations, custom scripts, partner integrations, VM images, stale base images, and service-to-service dependencies that nobody has touched in a long time,” Kathari explains. “These systems can keep working quietly for years, then fail during a DNS or certificate-related change because they bypassed the normal platform standards.”

Independent technology analyst Carmi Levy says that CIOs need to take this event very seriously. 

“The two-pronged deadline — October 11, 2026, when the new Key Signing Key (KSK) begins signing the root zone, and January 11, 2027, when the old key is retired — should be marked in red on everyone’s calendar, just as December 31, 1999, once was,” Levy says. “Failure to comply could result in websites, critical business applications, and related resources dropping off the face of the Earth once the transition is complete.”

Levy adds: “Custom-built code that lives outside conventional support mechanisms may or may not function when the DNS changes go into effect.”

The DNSSEC update itself is straightforward, but it is also the first significant DNSSEC change — specifically a change in the trust anchor — since 2018. 

The rollout statement noted that “the trust anchor is formally known as the Domain Name System Security Extensions (DNSSEC) root zone Key Signing Key (KSK). The KSK is the cryptographic key at the core of the DNSSEC trust anchor and is used to verify that DNS responses are legitimate and have not been modified in transit.”

Expect nearly every enterprise to be impacted

Kim Davies, vice president of IANA Services and president of public technical identifiers at ICANN, says the extent of the impact on enterprises is unknowable, given the nature of shadow IT and other edge cases. 

But based on the massive number of dependencies both known and unknown in the typical global enterprise, Davies guesses that just about every enterprise will be impacted, to varying degrees. 

“In highly complex organizations, it is very likely there will be some impact in the corners, in the margins, of the organization,” Davies tells CIO. “DNS is such a core technology that underpins everything.”

As the updates propagate, hiccups will materialize, Davies notes. “When the system cannot validate the [DNS] information, it will treat it as suspect and DNS lookups will fail.”

Visa’s Kathari says, “Enterprises should expect some secondary DNS-related glitches when major DNSSEC-related changes happen, not necessarily because the core infrastructure teams will ignore the update, but because large environments have many hidden dependency paths.”

Making this problem far worse, Kathari notes, is that the glitches will likely initially look like anything other thana DNS glitch. That will force IT staff to waste a vast number of hours chasing causes that ultimately prove to be unrelated to the incidents. 

“The impact for CIOs is that DNS failures rarely announce themselves as DNS failures. They look like application timeouts, broken logins, failed API calls, queue lag, payment failures, partner connectivity issues, or random regional instability,” Kathari explains. “That makes troubleshooting slower because teams may spend hours looking at the application, database, network, or cloud provider before realizing name resolution is part of the failure path.”

Sanchit Vir Gogia, chief analyst at Greyhound Research, agrees that IT will likely spin its wheels chasing the wrong ghosts.

“A validation failure rarely stays in its lane. It surfaces as an application error, an API timeout, or a reachability problem, which turns a resolver fault into a coordination failure,” Gogia says. “The application team blames the network, the network team blames the cloud, and the user simply watches work stop.”

“Images and templates are the frontier most teams miss,” Gogia adds. “A resolver fixed in summer can be broken again in October the instant a stale golden image is redeployed, because automation no longer lets configuration drift slowly. It restores yesterday’s assumptions at machine speed.”

It is widely expected that enterprises will not have any problems executing the change or, more likely, relying on their hyperscalers to properly handle the change. That is the concern. 

“CIOs are being distracted so much with AI and this is such a deep in the weeds infrastructure issue that this can and willcatch people off-guard,” Justin Greis, CEO of consulting firm Acceligence, tells CIO. “I think we’ll see a meaningful number of enterprise disruptions associated with the DNSSEC trust anchor rollover. Not because the update itself is especially difficult, but because it will expose weaknesses that already exist inside many organizations.”

Most enterprise IT operations have had no reason to compile a comprehensive list of all DNS dependencies, but many will be instantly discovered in January. 

Potentially widespread fallout

A major retailer, for example, might suddenly be unable to connect with FedEx to arrange for deliveries or a hospital may find that test results are no longer being shared with patient portals. It might manifest as an assembly line that halts because an IIoT component can no longer share files with its vendor system or a truck fleet that stops being tracked. 

“There will almost certainly be systems that fall through the cracks. Some will be legacy applications that rely on outdated DNS configurations that have not been updated in years,” Greis says. “Others will be business-unit-developed tools, contractor-built solutions, embedded systems, manufacturing and industrial systems, or highly customized workloads that operate outside normal IT oversight. These are the types of systems that often surface during infrastructure events like this.”

Greis adds that many enterprises will discover in January problems created by their own automation.

“Over time, enterprises build layers of processes, templates, and deployment mechanisms that are reused across teams and environments,” Greis notes. “Even after DNS infrastructure is updated correctly, older settings can inadvertently be reintroduced through routine updates and system changes, creating intermittent and difficult-to-diagnose failures.”

The good news from this situation is that enterprises are not going to likely lose all DNS access if any of these glitches occur. But that may be of no comfort because even if the disruptions are only with small edge cases, that can still cause massive operational disruptions.

Cricket Liu, EVP and chief evangelist at Infoblox, gives the example of a DNS server that responds to factory-floor system queries.

“Or let’s say this disrupts [an enterprise’s key] SaaS application. All name resolution may stop and it will show a server failure. It will not deliver a response whenever I look anything up. That’s not subtle at all,” Liu says. “It’s highly likely that companies are going to see some effects.”

Back in 2017, the switchover was relatively uneventful, giving some CIOs hope that January 2027 will also be a non-event. But given the technology advancements in the last 10 years and the resulting tidal wave of new enterprise tech dependencies, few are realistically expecting no problems this go around. 

Impossible to predict what will happen

One of the top network experts on DNS effects in enterprises is Geoff Huston, chief scientist at the Asia Pacific Network Information Centre (APNIC), the regional Internet Registry administering IP addresses for the Asia Pacific region.

Huston says it is difficult to project what will happen in January until it happens.

“Just like the last time, we are flying blind with this key roll. Because nothing really terrible happened last time, there is some confidence that nothing terrible will happen this time, but we just can’t tell in advance as there are no good measurement approaches that allow us to peek inside the trust state of recursive resolvers,” he says.

As for potential edge-case glitches, Huston says it is possible, but if third-party vendors do not properly handle the update, there will be other issues as well, as the KSK cryptographic key used within DNSSEC signs and validates the keys that protect DNS records. 

“If it is not standards-compliant, then you have more problems than just the KSK roll,” Huston says, “as it raises the obvious question of ‘What else is not correctly implemented in the DNS resolver that I’m running?’”

As a silver lining, Acceligence’s Greis says any hiccups that result from the DNS KSK update may be a gift in disguise for CIOs. 

“The irony is that some of the most business-critical components in the technology stack are often the least visible because they work in the background,” Greis says. January “may reveal how much modern business resilience depends on infrastructure that many organizations rarely examine until something breaks. For CIOs, that’s the real lesson. This is not fundamentally a story about a DNS update. It is a story about operational visibility, resilience, and governance. Organizations that treat the rollover as a routine infrastructure task will likely complete the update and move on. Organizations that use it as an opportunity to understand and strengthen the foundations of their technology environment may gain far more value than simply avoiding an outage.”

Four months of Claude Code — that’s all it took for Uber to burn through its entire annual budget for AI. Token after token, engineers embraced the platform with few control mechanisms tying costs to outcomes. The result was a budget runaway and a clear case study in how limited oversight snowballs into an AI blowout.

This is a phenomenon I like to call “shadow tokens” — AI credits paid for by the company but largely invisible to decision-makers. Too many engineers have the final say over how much they consume and, therefore, what it costs. This all-you-can-eat attitude is part of the reason why Microsoft is reportedly winding down many internal licenses across key engineering teams and why one in five organizations is missing its AI spend forecast by more than 50%.

And the trend is only accelerating. By 2028, Gartner predicts that AI coding costs (driven by this kind of ungoverned consumption) will be as much per developer as the salary companies pay that person.

LLMs and agents introduce a new class of variable cost that scales with behavior rather than headcount, putting enterprises on the hook for tools that balloon with workload. I don’t see this as enterprises overspending because they’re reckless — it’s down to a lack of managerial oversight, budget alignment that demands a proven return on investment, and engineer education on how much is too much.

Going forward, CIOs need to thread the AI needle between governance that encourages transparency and reasonable spend without stifling innovation.

When shadow tokens result in real costs

The issue is that AI isn’t a traditional line item. Previously, enterprise leaders onboarded software-as-a-service (SaaS) with a good idea of the total cost. An allocated software seat or annual contract was a known quantity. The cloud added some variation (with fluctuations depending on hosting size), but instances were still modelable. AI flips this status quo on its head — the unit of consumption is behavior and the cost is exponential.

And these specifics aren’t immediately apparent at pilot. Tools can appear inexpensive in controlled experiments yet unpredictably scale depending on session length, context window size, model selection and whether agents run in parallel. This is the fallacy of the $20-per-seat enterprise plan — tokens are charged separately at API rates with no ceiling. The final dollar value of any session is set by factors that finance can’t always model in advance, particularly when these decisions usually rest with the engineers themselves.

According to Deloitte, only 21% of organizations deploying agents have a mature governance model, a real concern because they’re token-eating machines. This is what was happening at Uber — Claude Code in agentic mode was autonomously reading codebases, planning changes across dozens of files and opening pull requests. Each step quickly adds up, with Anthropic’s own documentation noting that agents consume approximately seven times as many tokens as standard sessions.

This is shadow IT and shadow AI, evolved. This time, however, many leaders approved the tool in question without guardrails governing consumption. AI hype adds fuel to the fire and normalizes long sessions. Uber’s CTO, for example, described a company-wide shift toward “agentic software engineering” with employees “who are quietly experimenting, quietly shipping and quietly pushing things forward”. This is an exciting way to test the limits of what’s possible, certainly, but it’s also a position that goes a long way to explaining how the company spent its annual AI budget by April.

Shifting the culture from usage to yield

Engineers haven’t done anything wrong here. In fact, they’re adopting and experimenting as instructed, with Uber creating leaderboards and ranking users by token consumption. More use led to a better ranking, reflecting a culture that lauds new ways of doing things. This behavior is known as “tokenmaxxing,” and its principal knock-on effect is shadow tokens — quantity-over-quality processes that leaders struggle to control until they’re fully realized in the budget. Of course, if management treats adoption metrics as performance metrics, then engineers can’t be blamed for using more tokens. The tension is that the teams driving adoption aren’t the ones managing spend.

None of this is meant to dismiss AI’s productivity possibilities and potential return on investment. Developers save 3.6 hours per week, achieve 60% higher pull request throughput and cut onboarding time in half with automation. Meanwhile, Uber shared that roughly 11% of live backend updates were written by agents with no human in the loop. However, these wins aren’t the problem — it’s that too many teams aren’t connecting input to output. I’ve spoken to admins who discovered their token spend had tripled in a single quarter after using heavier models or accidentally doubling up on agentic applications. Nobody knew until the financial damage was done.

Automation needs to happen sustainably with an eye on the bottom line. In my view, a much better metric for achieving this is AI yield — the measurable business or engineering output generated per dollar spent on tokens. Otherwise, without a feedback loop, even genuinely productive teams are flying blind.

Stopping token waste before an AI blowout

Creating that throughline between AI investment and token consumption starts with established financial metrics. This is possible via maximum spend limits (dictated by spend tagging, workload tiering and cost-per-output benchmarks) per team or project. Then, any additional allocation requires approval, closing the loop between the engineers spending the tokens and the leaders paying for them. AI isn’t cheap and teams should demonstrate a bang for their buck.

This is something we do with our engineering team at Hexnode. Resource allocation for Claude Code and Cursor is tied directly to ROI rather than letting consumption run open-ended. Given the pay-as-you-go nature of these tools, a firm usage limit per team offers simple but essential control.

Similarly, there’s room to apply some of the governance principles IT uses for device management. Things like policy enforcement, role-based access, real-time monitoring and automated alerts can flag usage behavior in advance. Uncovering such insights at the token layer works to identify power users and prevent excessive spending.

We also need to encourage cultures that praise outputs that actually achieve efficiency. AI applications that result in shipping faster, reducing rework and cutting review cycles are gains that should be celebrated. If your company hosts leaderboards, frame unnecessary token burn as wasteful rather than valuable. The organizations creating healthier consumption habits work with their engineers to understand not just how to use AI, but what responsible use looks like and what it costs.

This is a conversation teams need to have now. Anthropic just ended flat-rate pricing for programmatic workloads from June 15. Now, agents, continuous integration pipelines and automated workflows draw from a dedicated monthly credit pool billed separately from the subscription. Once that pool is exhausted, agent tasks either stop entirely or overflow to extra billing. Work can either get very expensive or grind to a halt for teams that aren’t prepared.

Getting a grip on shadow tokens means better rules and tools connecting spend to outcomes. Only by building the financial and cultural infrastructure that encourages sustainable adoption can leaders see what they’re spending, connect it to what they’re getting and course-correct before the costs become a crisis. Ultimately, shadow tokens are only invisible if we choose not to look.

This article is published as part of the Foundry Expert Contributor Network.
Want to join?

Predicting an outage is tricky business, but CIOs might want to circle Oct. 11, 2026, through Jan. 11, 2027, for likely trouble of a potentially widespread and puzzling nature.

That’s because a relatively trivial update to DNSSEC on Oct. 11, one that will take full effect by Jan. 11, is likely to deliver a series of seemingly unrelated system outages. This will come from oceans of dependencies from third-party, shadow, agentic, gen AI, SaaS, homegrown, and legacy apps — among many other quiet executable hiding spots, including virtual environments and containers.

Sai Joshitha Kathari, senior site reliability engineer at payment card giant Visa, says most enterprises have far more DNS-related exposure than they realize because of these many dependencies.

“This has the potential to create real downstream destruction when unresolved failures sit underneath important business functions,” Kathari says. 

The danger is that so many of these issues are either unknown to IT or handled by a third-party vendor and no one in IT has had reason to ask those vendors about DNS updates. 

“The risky areas are usually not the obvious managed DNS services. They are the older internal applications, hardcoded resolvers, containerized workloads, sidecar configurations, custom scripts, partner integrations, VM images, stale base images, and service-to-service dependencies that nobody has touched in a long time,” Kathari explains. “These systems can keep working quietly for years, then fail during a DNS or certificate-related change because they bypassed the normal platform standards.”

Independent technology analyst Carmi Levy says that CIOs need to take this event very seriously. 

“The two-pronged deadline — October 11, 2026, when the new Key Signing Key (KSK) begins signing the root zone, and January 11, 2027, when the old key is retired — should be marked in red on everyone’s calendar, just as December 31, 1999, once was,” Levy says. “Failure to comply could result in websites, critical business applications, and related resources dropping off the face of the Earth once the transition is complete.”

Levy adds: “Custom-built code that lives outside conventional support mechanisms may or may not function when the DNS changes go into effect.”

The DNSSEC update itself is straightforward, but it is also the first significant DNSSEC change — specifically a change in the trust anchor — since 2018. 

The rollout statement noted that “the trust anchor is formally known as the Domain Name System Security Extensions (DNSSEC) root zone Key Signing Key (KSK). The KSK is the cryptographic key at the core of the DNSSEC trust anchor and is used to verify that DNS responses are legitimate and have not been modified in transit.”

Expect nearly every enterprise to be impacted

Kim Davies, vice president of IANA Services and president of public technical identifiers at ICANN, says the extent of the impact on enterprises is unknowable, given the nature of shadow IT and other edge cases. 

But based on the massive number of dependencies both known and unknown in the typical global enterprise, Davies guesses that just about every enterprise will be impacted, to varying degrees. 

“In highly complex organizations, it is very likely there will be some impact in the corners, in the margins, of the organization,” Davies tells CIO. “DNS is such a core technology that underpins everything.”

As the updates propagate, hiccups will materialize, Davies notes. “When the system cannot validate the [DNS] information, it will treat it as suspect and DNS lookups will fail.”

Visa’s Kathari says, “Enterprises should expect some secondary DNS-related glitches when major DNSSEC-related changes happen, not necessarily because the core infrastructure teams will ignore the update, but because large environments have many hidden dependency paths.”

Making this problem far worse, Kathari notes, is that the glitches will likely initially look like anything other thana DNS glitch. That will force IT staff to waste a vast number of hours chasing causes that ultimately prove to be unrelated to the incidents. 

“The impact for CIOs is that DNS failures rarely announce themselves as DNS failures. They look like application timeouts, broken logins, failed API calls, queue lag, payment failures, partner connectivity issues, or random regional instability,” Kathari explains. “That makes troubleshooting slower because teams may spend hours looking at the application, database, network, or cloud provider before realizing name resolution is part of the failure path.”

Sanchit Vir Gogia, chief analyst at Greyhound Research, agrees that IT will likely spin its wheels chasing the wrong ghosts.

“A validation failure rarely stays in its lane. It surfaces as an application error, an API timeout, or a reachability problem, which turns a resolver fault into a coordination failure,” Gogia says. “The application team blames the network, the network team blames the cloud, and the user simply watches work stop.”

“Images and templates are the frontier most teams miss,” Gogia adds. “A resolver fixed in summer can be broken again in October the instant a stale golden image is redeployed, because automation no longer lets configuration drift slowly. It restores yesterday’s assumptions at machine speed.”

It is widely expected that enterprises will not have any problems executing the change or, more likely, relying on their hyperscalers to properly handle the change. That is the concern. 

“CIOs are being distracted so much with AI and this is such a deep in the weeds infrastructure issue that this can and willcatch people off-guard,” Justin Greis, CEO of consulting firm Acceligence, tells CIO. “I think we’ll see a meaningful number of enterprise disruptions associated with the DNSSEC trust anchor rollover. Not because the update itself is especially difficult, but because it will expose weaknesses that already exist inside many organizations.”

Most enterprise IT operations have had no reason to compile a comprehensive list of all DNS dependencies, but many will be instantly discovered in January. 

Potentially widespread fallout

A major retailer, for example, might suddenly be unable to connect with FedEx to arrange for deliveries or a hospital may find that test results are no longer being shared with patient portals. It might manifest as an assembly line that halts because an IIoT component can no longer share files with its vendor system or a truck fleet that stops being tracked. 

“There will almost certainly be systems that fall through the cracks. Some will be legacy applications that rely on outdated DNS configurations that have not been updated in years,” Greis says. “Others will be business-unit-developed tools, contractor-built solutions, embedded systems, manufacturing and industrial systems, or highly customized workloads that operate outside normal IT oversight. These are the types of systems that often surface during infrastructure events like this.”

Greis adds that many enterprises will discover in January problems created by their own automation.

“Over time, enterprises build layers of processes, templates, and deployment mechanisms that are reused across teams and environments,” Greis notes. “Even after DNS infrastructure is updated correctly, older settings can inadvertently be reintroduced through routine updates and system changes, creating intermittent and difficult-to-diagnose failures.”

The good news from this situation is that enterprises are not going to likely lose all DNS access if any of these glitches occur. But that may be of no comfort because even if the disruptions are only with small edge cases, that can still cause massive operational disruptions.

Cricket Liu, EVP and chief evangelist at Infoblox, gives the example of a DNS server that responds to factory-floor system queries.

“Or let’s say this disrupts [an enterprise’s key] SaaS application. All name resolution may stop and it will show a server failure. It will not deliver a response whenever I look anything up. That’s not subtle at all,” Liu says. “It’s highly likely that companies are going to see some effects.”

Back in 2017, the switchover was relatively uneventful, giving some CIOs hope that January 2027 will also be a non-event. But given the technology advancements in the last 10 years and the resulting tidal wave of new enterprise tech dependencies, few are realistically expecting no problems this go around. 

Impossible to predict what will happen

One of the top network experts on DNS effects in enterprises is Geoff Huston, chief scientist at the Asia Pacific Network Information Centre (APNIC), the regional Internet Registry administering IP addresses for the Asia Pacific region.

Huston says it is difficult to project what will happen in January until it happens.

“Just like the last time, we are flying blind with this key roll. Because nothing really terrible happened last time, there is some confidence that nothing terrible will happen this time, but we just can’t tell in advance as there are no good measurement approaches that allow us to peek inside the trust state of recursive resolvers,” he says.

As for potential edge-case glitches, Huston says it is possible, but if third-party vendors do not properly handle the update, there will be other issues as well, as the KSK cryptographic key used within DNSSEC signs and validates the keys that protect DNS records. 

“If it is not standards-compliant, then you have more problems than just the KSK roll,” Huston says, “as it raises the obvious question of ‘What else is not correctly implemented in the DNS resolver that I’m running?’”

As a silver lining, Acceligence’s Greis says any hiccups that result from the DNS KSK update may be a gift in disguise for CIOs. 

“The irony is that some of the most business-critical components in the technology stack are often the least visible because they work in the background,” Greis says. January “may reveal how much modern business resilience depends on infrastructure that many organizations rarely examine until something breaks. For CIOs, that’s the real lesson. This is not fundamentally a story about a DNS update. It is a story about operational visibility, resilience, and governance. Organizations that treat the rollover as a routine infrastructure task will likely complete the update and move on. Organizations that use it as an opportunity to understand and strengthen the foundations of their technology environment may gain far more value than simply avoiding an outage.”

Over the past year, I had the same conversation with almost every team starting an AI initiative. Should we build on Semantic Kernel, AutoGen or Foundry?

At first it felt like the most important architectural decision we’d make. Each framework had its own philosophy, each promised to be the foundation for enterprise AI, and picking the wrong one felt like an expensive mistake. I spent a lot of time helping teams weigh the trade-offs.

Looking back, I think we were asking the wrong question. I certainly was.

I watched teams spend months debating SDKs while the decisions that actually decided whether their applications survived production went unexamined. Some built elaborate orchestration layers for workflows that a few deterministic functions would have handled. Others avoided agent frameworks entirely and later found they’d designed themselves into a corner.

Then Microsoft settled it for us. It introduced the unified Agent Framework, quietly moved Semantic Kernel and AutoGen into maintenance mode, and the debate I’d spent months refereeing was suddenly over. Turns out the answer to “which of the three” was “none of the three, here’s a fourth.” The framework hit version 1.0 and general availability in April 2026, stable across .NET and Python.

What surprised me wasn’t the decision. It was how fast a debate that had eaten so much of our attention stopped mattering. Microsoft changed the menu.

It didn’t change the meal.

The framework was never the hard part

Framework selection dominated almost every early conversation I had about enterprise agents. Which SDK do we standardize on? Which orchestration model gives us the most flexibility? Which one is Microsoft actually betting on?

Fair questions. But after a year of watching these projects play out, I’ve slowly come around to a different view. Those weren’t the questions that decided anything.

The first question I ask now is much smaller. Does this thing actually need an agent?

It sounds obvious, and I still get it wrong sometimes. But it’s the mistake I see most. On one project, a team spent weeks designing a multi-agent workflow for a process that ran the same four steps every time: read a document, validate it, call an API, send a notification. The diagrams looked great. The system in production didn’t. A few well-tested functions would have been easier to build, easier to maintain and a lot easier to trust.

Part of this is just that “agent” has become the word everyone reaches for. Sometimes it’s the right call. Sometimes it’s a workflow we already knew how to build, wearing a newer label. An agent earns its complexity when it genuinely has to decide things you can’t predetermine, choosing between tools, adapting to what it finds, working out its own next step. If you already know every step, you have a workflow, and a workflow is usually the better engineering choice. The consolidation didn’t change that. It just made it easier to see.

What building production agents actually taught me

Once I stopped fixating on frameworks, the same three problems kept showing up. None of them had anything to do with the SDK.

Context beats model choice

Early on I spent a lot of time comparing models, the way you’d agonize over a restaurant menu and then order what you always order. Now I spend most of it thinking about context, which is far less fun and far more useful.

I’ve watched good models fail because they were handed too much, not too little. One team I worked with gave the model access to nearly every internal document they had on the theory that more information meant better answers. It went the other way. Responses got slower, less consistent and sometimes skipped right past the thing that actually mattered. When we cut the context down to only what the task needed, the quality jumped almost immediately. I didn’t predict that. It taught me to be suspicious of “just give it everything.”

The best agent systems I’ve worked on weren’t the ones with the biggest context windows. They were the ones careful about what reached the model, and when. That’s not something the framework hands you.

Failure is where the real work is

Most agent demos look great because they’re built around the happy path. Production doesn’t extend that courtesy.

I remember a project where everything held up in testing. Then a downstream API timed out after the agent had already completed several earlier steps. We couldn’t just restart, because part of the business process had already gone through. We ended up spending far more time on recovery logic than we ever spent on prompts. That project changed how I think about this work. The hard part was never getting the model to make a decision. It was making sure the system didn’t fall apart when reality refused to follow the script.

Tool calls fail partway through. APIs return inconsistent data. Models call the same tool over and over because the last answer wasn’t what they wanted. That’s not the exception; that’s a normal Tuesday. Whether you retry, roll back, pause for a human or push on with partial results is a judgment call, and no framework is going to make it for you.

Identity is the real security boundary

This one surprised me most. The moment an agent stops being a chatbot and starts touching real business systems, identity matters more than orchestration.

Every project gets to the same question eventually. Who is this agent actually acting as? The developer’s credentials? A service account? The user who asked? Get it wrong and you’ve built something autonomous running with more access than any single person should have, which is exactly the kind of thing that looks fine until an audit. The Agent Framework, like most modern tooling, makes it easier to wire agents to tools through standards like the Model Context Protocol. That helps. But where human approval belongs, what needs extra authorization, how much rope to give the thing, those are still yours to decide.

The surprises weren’t technical

Here’s what I didn’t see coming. The hardest part of last year wasn’t technical at all. It was organizational. The moment a team heard “agent,” expectations shifted under everyone’s feet. Business stakeholders started expecting full autonomy. Developers assumed the thing could reason its way through anything. People started designing for flexibility before we’d even agreed on what problem we were solving. The word did damage before any code did. I found myself spending as much time resetting expectations as I did discussing architecture.

Build for change, not for today’s winner

I don’t think the teams that struggled last year picked the wrong framework. Semantic Kernel was reasonable. AutoGen was reasonable. Foundry made sense for plenty of cases. I’d have signed off on any of them.

The ones that got hurt put all their eggs in one framework, treating it as the foundation of the whole system instead of as one more dependency. Microsoft provided a migration path. But teams that had tightly coupled their applications to framework-specific abstractions discovered that migrating and rewriting are not the same thing. That wasn’t Microsoft’s doing. It was their own architecture’s. The teams that moved easily had kept their business logic, prompts and orchestration loose enough to evolve independently of any one SDK. For them, the change was a manageable project, not a teardown.

For what it’s worth, nobody I work with is treating this as an emergency. Most are moving the smaller workloads first, watching how they behave and leaving the production-critical systems alone until they actually understand the new abstractions. That’s the right instinct. And I doubt this is the last consolidation we’ll see, the ecosystem is still young, frameworks will keep absorbing each other and over time the differences between them will be operational more than architectural.

I don’t regret the framework debates, honestly. They were reasonable at the time. What changed wasn’t Microsoft’s roadmap.

It was mine. Watching these systems run in production taught me that the framework is the easiest piece to swap out. Recovery logic, context management, security boundaries, the business workflow itself, those stay with you long after today’s SDK gets replaced by tomorrow’s.

So, Microsoft made one decision easier by turning three frameworks into one. Good. Five years from now we’ll be on different tools, and we’ll still be asking the same handful of questions.

Does this actually need an agent? Does it have the right context? Can it recover when something breaks, because something will? Is it acting as the right person?

Those questions outlast every rewrite. That’s where I’ve learned to put my effort.

Frameworks come and go. Good architecture has to survive all of them.

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Late in a large enterprise SAP transformation, the strategic governance conversations began to drift. Instead of executive decisions, we found ourselves debating whether the program needed dedicated testing, whether cutover required a full weekend, whether twenty Agile teams really needed coordination support and whether offshore resources were adding value at all.

The questions were not coming from the delivery teams. They were coming from the executive sponsor.

The sponsor had recently been elevated into a senior leadership role and had never sponsored a technology transformation at this scale. The challenge was not authority. The sponsor had every right to ask any question they wanted. The challenge was that strategic governance had quietly turned into a debate about delivery practices, because the sponsor did not yet have the transformation context to focus the conversation anywhere else.

This is not a story about a bad sponsor. The executive in this case was a capable senior leader with strong judgment and authentic intent. They had been placed into a role they had not yet been prepared for, and the pattern that followed was structural, not personal. It is one of the more common patterns I have observed across enterprise transformation programs, and one of the most consistently misdiagnosed.

Most program failures are not execution failures. They are sponsor mismatches.

When governance becomes a debate about delivery practices

When the sponsor does not understand what an enterprise transformation actually requires, governance forums stop functioning as decision bodies and start functioning as practice debates.

You see it in the questions that get asked. Why do we need a dedicated testing phase? Can the Build timeline be compressed? Why does cutover need a full weekend? Why do we need more Scrum Masters across 20 product teams? Can the US team simply work longer hours instead of using offshore resources? On one program, the sponsor suggested shifting the entire project’s working hours to India time, despite roughly 85 percent of the delivery organization being based in the United States.

None of these questions are unreasonable in isolation. Each one targets a real cost or timeline pressure. The problem is what is missing underneath them: an understanding of the operational risks the original choices were designed to mitigate.

When sponsors ask delivery-practice questions without that context, the program leadership team ends up defending the work instead of advancing it. Decision velocity drops. Trust between the program and its sponsor erodes. Senior delivery talent disengages from governance forums where the conversation never reaches the decisions they need made. What looks from the outside like an active sponsor producing engagement is, from inside the program, an active drain on the cycles needed to deliver.

The compounding cost is not unique to any single program. PMI’s research on executive sponsorship consistently identifies sponsor engagement quality, rather than sponsor presence alone, as one of the strongest predictors of project success. The visible symptom is debate. The actual cost is unmade decisions.

Authority is rarely the issue. Literacy is

When transformations stall under a mismatched sponsor, the diagnostic instinct is to question the sponsor’s authority. Are they senior enough? Do they have the cross-functional reach? Can they unblock?

In most of the programs I have led or advised, authority was not the limiting factor. The sponsor in the SAP program above had ample authority. They could unblock any decision the program needed. What had not been developed was the transformation literacy to know which decisions mattered, which were technical noise and which were execution risks that should not be optimized away.

This is what I have come to think of as the literacy problem. Sponsors elevated into transformation roles often have deep functional expertise (finance, operations, business unit leadership) but limited exposure to the distinct functions of PMO, organizational change management, agile delivery, testing and cutover, and how each one reduces a specific category of implementation risk. They are not expected to be SAP configuration experts. But they need enough transformation literacy to recognize which questions actually belong in a steering committee.

Harvard Business Review’s research on effective executive sponsorship has emphasized that sponsorship effectiveness depends as much on judgment as on authority. Judgment is where literacy becomes operational. A sponsor with authority but limited transformation literacy will optimize for speed and cost in ways that consistently underestimate risk. A sponsor with both will make the tradeoffs the program actually needs.

Prosci’s longstanding benchmark studies on change management have ranked active and visible executive sponsorship as the single greatest contributor to change success for two decades. The word that matters in that finding is active. Active sponsorship without transformation literacy can introduce real cost. Not because the sponsor is acting against the program, but because the optimization choices they make are based on incomplete information about what the program is built to protect against.

Shift the conversation from delivery practices to business risk

When the sponsor relationship is already in place and cannot be changed, the program leadership team has one move that consistently works: shift the conversation.

On the SAP program above, we stopped explaining why the testing phase existed. We started explaining the business risk of reducing it. We stopped debating the number of Scrum Masters. We started connecting delivery capacity to coordination across more than twenty Agile teams and the business cost of losing that coordination. We reframed offshore support as a way to maintain delivery momentum around the clock rather than asking the U.S. team to sustain fifteen-hour days.

The shift is from defending delivery practice to explaining business risk. The sponsor does not need to understand why testing takes the time it does. They need to understand what the program is exposed to if testing is compressed. They do not need to know how many Scrum Masters are statistically optimal for twenty Agile teams. They need to know what coordination breaks when the number is wrong.

This reframing accomplishes two things. First, it brings the conversation back to the level at which sponsors actually make decisions: tradeoffs between business outcomes and business risks. Second, it builds transformation literacy in the sponsor over time, almost as a byproduct. By the third or fourth iteration of business-risk-framed conversations, the sponsor begins to ask the right questions on their own.

In practice, this happens through small but deliberate moves. When the sponsor asks why a phase needs the time it takes, the program lead names two or three things that could go wrong if the time is cut and what each would cost the business. When the sponsor asks why a role is needed, the program lead names the work that would not get done without it. Every delivery-practice question gets converted into a business-risk answer.

The program leadership team’s job is not to make the sponsor an expert in SAP delivery. It is to provide enough transformation context so that executive decisions reflect both business priorities and implementation realities.

There are a few phrases I have used with executive sponsors over the years that capture the underlying issue. The sharpest one:

If the decision has to go above the sponsor, they are not the sponsor.

Sponsorship is defined by what the sponsor can decide without asking someone else. That is the test. Anything else is the appearance of sponsorship, not the substance.

For CIOs supporting enterprise transformation, the implication is direct. Sponsor selection, or sponsor preparation when selection is not an option, is not a hierarchy question. It is a transformation capability question. The same execution discipline that goes into defining decision rights, structuring governance and protecting delivery momentum should apply, with equal rigor, to assessing sponsor fit and building sponsor literacy before the program begins.

A sponsor does not need to be the technical expert. They do need to know when to trust the people who are.

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Revenue from IBM’s z mainframe portfolio declined 42% in the quarter ended June 30, dragging infrastructure revenue down 7% compared to the year-ago quarter. But Big Blue executives remain positive on the mainframe’s role as an important AI platform.

After warning of an earnings shortfall, IBM lowered its full-year forecast. It now expects 2026 revenue to grow between 4% and 5%, rather than its previous forecast of more than 5% growth. Some parts of its business did well: Software revenue grew 5% in the second quarter to $7.76 billion, fueled by 11% growth in hybrid cloud, 18% growth in data, and 3% growth in automation.

On the infrastructure side, IBM posted second-quarter revenue of $3.8 billion, which is down 7%. Within that business, distributed infrastructure grew 37%, but those gains were offset by a 10% decline in hybrid infrastructure and IBM Z’s 42% drop.

In a July 14 letter to investors released prior to IBM’s July 22 earnings call, CEO Arvind Krishna warned of the earnings shortfall and laid out current challenges. He related the infrastructure performance shortfall to “wrapping on the launch of z17 in the second quarter” and stated: “Given this was the strongest start to a mainframe program in our history, we expected Infrastructure revenue to decline low-single digits for the year, beginning this quarter. What played out was worse than our expectations, driven by a shortfall in our Z performance and the associated software stack, primarily in Transaction Processing.”

In the last few weeks of June, customers shifted capex spending and started purchasing more AI infrastructure components in the form of servers, storage, and memory “to secure supply-constrained infrastructure ahead of expected price increases,” Krishna stated. “This dynamic impacted client buying patterns. While we anticipated some supply chain related impact in our expectations, we did not anticipate the magnitude of the capex reprioritization.”

Yet despite challenges this last quarter, z17 remains at nearly 130% growth program-to-program, according to IBM. That’s “well ahead of z16, which was our strongest program on record, with clients representing 85% of installed MIPs maintaining or growing capacity,” the July 14 letter stated.

Mainframe infrastructure momentum is expected to continue, and IBM is anticipating strong workload growth and AI-driven capacity expansion as clients modernize mission-critical systems and emphasize resiliency and security, Krishna said during the company’s Q2 2026 earnings call on July 22.

“AI is driving incremental capacity growth and new workloads as clients look to run AI closer to their most sensitive data,” IBM senior vice president and CFO James Kavanaugh said in the call. “We are seeing strong early adoption of our AI innovations with nearly 50% of z17 customers investing in AI capabilities with Spyre AI accelerator, and clients deploying Watson X Code Assistant for Z are growing MIPS capacity three times faster than those who are not.”

“In a world where infrastructure costs are rising and efficiency matters more than ever, IBM Z offers a compelling economic advantage,” Kavanaugh continued. “Depending on the size and complexity of workloads, clients can realize a 2 to 15x total cost of ownership benefit versus moving these workloads off the platform, reinforcing why the platform remains central to their operations and positioning us to capture additional value as AI workloads grow.”

“We see no evidence of clients moving off mainframe,” Kavanaugh added. “Clients continue to invest in IBM Z to modernize mission-critical workloads with a focus on resiliency and security.”

In responding to an analyst question, Kavanaugh said three key things drive mainframe demand and purchasing requirements:

“One is capacity workload. It’s the most important determinant. 85% Of the installed MIPS capacity out there in the marketplace today running all those core mission critical workloads are either stable or growing. Clients are adding capacity and workload to mainframe, the viability. And by the way, that’s coming in new AI workloads, analytics workloads, Linux-based workloads, and those MIPS are growing program to date over 15 to 20% installed capacity,” Kavanaugh said.

Number 2 is economic factors. “We don’t talk a lot about this, but I think it’s important for our investors to understand things like total cost of ownership. Depending on the size and complexity of the workload, we have anywhere from a 2 to a 15x TCO advantage running on the mainframe [over smaller server systems]. Again, we do not see any evidence of clients migrating off mainframe and lease propensity, which is a great indicator,” Kavanaugh said.

The third driver is AI. “When you look at it, applications, data security, all on the platform, we do 450 billion inferences per day at 1 millisecond with 8 nines availability,” Kavanaugh said. “We’ve got clients that have already purchased over 50% of our Spire inferencing, and those clients that have purchased that are growing MIPS capacity, the way [we monetize value], by over three times faster than others.”

Cloudflare recently beat Q1 2026 earnings. Revenue up 34% year over year. EPS ahead of consensus. Full-year guidance raised. Then, in the same breath, they announced 1,100 layoffs, 20% of the company. CEO Matthew Prince’s explanation: “The way we work at Cloudflare has fundamentally changed.”

Block did the same thing. Beat guidance, raised outlook, cut 4,000+ jobs. Both framed it as architecting for the AI era.

This is not a contradiction. This is the new math boards are running. And if you’re a CIO who hasn’t started running it yourself, you’re behind.

The benchmark has moved

AI-native companies have quietly reset what “efficient” means for a technology organization. Midjourney generates over $500M in revenue with roughly 160 employees, over $3M per head. Anthropic hit a $14B annualized run rate in early 2026 with fewer than 3,000 employees. Across the top AI-native startups, the average revenue per employee is $3.48M, nearly twelve times the traditional SaaS benchmark of $300K.

Boards aren’t comparing you to your 2019 self anymore. They’re comparing you to Anthropic.

This is the pressure Cloudflare and Block are responding to. They’re not cutting people because the business is struggling. They’re cutting because investors have internalized a new denominator. Headcount is no longer a proxy for capacity; it’s a liability on the efficiency ratio.

For CIOs, this creates a hiring problem that looks nothing like the cloud or mobile talent gaps of the past decade. Those gaps were about volume: hire 100 cloud engineers, absorb the cost, build the capability… This one is about density; you’re not looking for 100 people. You’re looking for 10 who can deliver what 100 couldn’t, and justify $1M or more in value per seat.

Finding bodies to fill seats has never been easier. Finding people who operate at that level of leverage is a different problem entirely.

‘Acqui-hires’ are a shortcut with a hidden cost

Companies have figured out that recruiting AI-native talent one by one is too slow and that it’s faster to buy a team. Google’s acquisition of the Windsurf founders, Meta bringing in the Scale AI team, Accenture’s string of AI-focused acquisitions: these are acqui-hires dressed up as M&A. The premium on experienced AI talent is high enough, and the urgency real enough, that organizations are skipping traditional hiring loops entirely and buying their way in.

I’ve been on the other side of this. My company, MadKudu, was acquired by HG Insights specifically to bring AI-native capability into an established enterprise business. HG needed change agents who had already figured out how to build and ship in this new era, not just people who’d read about it. That’s the thesis behind most of these deals.

But there’s a cost that doesn’t show up in the acquisition price.

AI-native teams are fast because they operate with a different set of defaults: full access to tools, minimal governance layers, the ability to experiment and ship without a six-week approval cycle. That operating model is not a perk; it’s the fundamental mechanism. It’s why a team of 10 can do what an enterprise team of 100 can’t.

When you acqui-hire that team and then slot them into your existing approval processes, you’ve bought the people and killed the engine. The change agents you paid for become change-frustrated. The attrition that follows is expensive and predictable.

The harder realization: acquiring an AI-native team means accepting how they work. That requires deliberately carving out space for them to operate differently, not just tolerating it but institutionalizing it. The acquisition is an organizational change program, not just a hiring event.

The CIO’s real problem

The governance stack most enterprise organizations run was designed for a headcount world. Every tool vetting cycle, every vendor review, every security approval was calibrated assuming you were managing a large team where consistency and control were the primary objectives.

That calculus breaks when your goal is talent density. The same approval processes that protect against data leaks are now the reason your best people can’t do their best work. When it takes six weeks to approve a tool that your competitor’s team is already shipping with, you’ve traded velocity for the perception of safety.

The practical fix is structured experimentation: clear guardrails, defined boundaries, but explicit permission to try tools before deciding whether to roll them out broadly. Gating everything prevents you from ever discovering what 10x productivity looks like.

The skills inventory question is also more nuanced than it sounds. Job titles won’t tell you where the leverage is. You need to map the actual tasks within each function and assess which can be automated or augmented with AI. That’s where you find the people who, with the right tools, become your $1M/employee talent, not because you hired differently, but because you enabled better.

This is also where the build-versus-buy question gets genuinely tricky. As AI reshapes how products are built and delivered, your internal operating model — how you work, how fast you ship, how you use data — is becoming core IP. Outsourcing delivery means outsourcing the part of the organization where your competitive advantage is now being built.

Closing the gap without slowing down

The AI talent wars are not primarily a recruiting problem. They’re a rethinking of what organizations are supposed to look like.

Boards have a new benchmark. Cloudflare, Block, Amazon, Meta and others have already started restructuring to meet it, publicly, painfully, even while beating their numbers. The question for CIOs isn’t whether this pressure arrives; it’s whether you’re ahead of it or behind it when it does.

The organizations that navigate this well won’t win by outbidding competitors for a handful of elite engineers. They’ll win by designing operating systems that amplify the leverage of the talent they do have, by enabling their best people rather than constraining them, and by treating AI fluency as a core organizational capability rather than a niche specialization.

Talent density is the new headcount model. The sooner your governance, your tooling and your board conversations reflect that, the better positioned you’ll be when the next efficiency report lands.

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I haven’t slept much in the past few weeks. Not because of some theoretical cyber risk that keeps many executives awake, but because reality just delivered a real wake-up call to our industry — a call that every executive must answer, now.

Imagine this: A major global enterprise, a company most of us interact with indirectly every single day, wakes up to find its entire digital environment obliterated. Thousands of employees in dozens of offices and remote locations are suddenly offline. Customers are cut off, supply chains grind to a halt and regulators are notified with a chilling admission: “We have no idea when we’ll be back.”

This wasn’t ransomware. There was no negotiation, no decryption key to buy, no easy way out. It was destruction — deliberate, coordinated and geopolitically motivated — not monetary.

As a chief customer officer who’s worked with countless customers on cyberattack risks, my perspective hits a bit differently than a CISO or a CTO. I see the aftermath, not just the attack surface. I see the faces behind the tickets, the operations team locked out of their own systems, the support agent answering panicked calls at dawn. And I ask: How many organizations have actually stress-tested their response to this scenario — not a hypothetical, but this very real, lights-out event? Here’s what every leader needs to confront today:

Recovery is not just a technical exercise

The first assumption to break during a real crisis is the belief that recovery is purely technical.

Many organizations have done tabletop exercises and have a backup and recovery playbook, so they feel prepared. They can point to backup windows, retention schedules and immutability controls. The moment a true blackout happens, a different reality surfaces. The people who own the recovery steps either do not know each other, lack the authority to make decisions without supervisor approval or need guidance from offline systems.

The reality is that technical infrastructure almost always holds up better than human infrastructure. Organizations have built their recovery strategy around the assumption that someone competent will be awake, available and empowered when a cyber event happens.

Still, backups are only as good as their independence. Let’s be blunt: If your recovery infrastructure shares identity, authentication or network trust with your Microsoft tenant (such as Azure, Microsoft 365 or Teams), you don’t actually have a recovery plan; you have a false sense of one — and a liability. A recent survey found that while 90% of organizations express confidence in their ability to recover from a cyber incident, fewer than one in three ransomware victims fully recovered their data.

True resilience means immutable, air-gapped backups, untouchable by the same compromise. Anything less is an illusion. I talk to customers about their recovery plans constantly. The customers who have rehearsed all scenarios sleep soundly. Those who haven’t? They’re rolling the dice.

Most business continuity plans ignore ‘total blackout’

I’ve reviewed hundreds of business continuity plans. Almost all assume partial failures — a region, an application, a data center. But what if every system, in every country, goes dark simultaneously? That’s an entirely different playbook. If your team hasn’t run a drill for a global, simultaneous outage, you’re not prepared. The probability is low, but the cost of being unready is existential.

Connected devices, OT systems, field hardware, partner integrations — they all plug into your enterprise network. When the core collapses, it’s not just IT at risk. It’s operational technology, physical safety systems and in regulated sectors, potentially human lives. Understanding and testing those interdependencies is non-negotiable.

This is also where boards need to change the conversation. A study found that only 5% of companies have cybersecurity experts on their board of directors. Recovery time objectives (RTOs) should not be buried in technical appendices. It’s all jargon to boards. That makes translation essential. RTOs must be explained in terms of business impact. “We can recover in four hours” is a technical statement. “Every hour of downtime costs us $2.3M and creates regulatory exposure in three jurisdictions” is a board statement.

That is the level of clarity leaders need.

The most prepared organizations do not wait for an incident to educate the board. They bring the conversation forward proactively. They frame recovery in business terms: revenue, regulatory standing, customer trust and brand reputation.

The most effective framing is often simple. Show the most critical systems. Show what happens if each one is down for one hour, four hours, 24 hours and 72 hours. Show the current recovery capability against each and then show the gap.

If your board is not demanding real answers, your business continuity strategy is likely underfunded and your business is exposed. This is a risk conversation worth forcing because the consequences do not stay inside IT. They can show up in customer churn or missed revenue and ruin an organization’s reputation.

Threat intelligence must be actionable, not archived

Geopolitical attacks, hacktivist campaigns and nation-state targeting aren’t abstract threats. They are active risks, and that intelligence cannot languish in the security team’s inbox. Executive leadership must be looped in — and immediately — so gaps can be closed before they’re exploited. Too often, intelligence enters the security operations function and never reaches the teams responsible for recovery infrastructure or executive decision-making.

If a threat actor is targeting a specific class of backup agents, the team responsible for those agents needs to know now, not two weeks from now. If intelligence suggests destructive activity against a sector, recovery owners need to validate isolation, access paths and restoration procedures immediately. If geopolitical tension increases the likelihood of targeting, executive leadership needs to understand what exposure exists and what actions are being taken. The organizations that survive aren’t just the best at incident response. They’re the ones who anticipated, rehearsed and invested before the attack.

Part of investing in a recovery strategy requires closing the loop between signal and action. The most prepared organizations have already mapped their critical recovery dependencies to specific threat categories. When intelligence touches one of those categories, there is a named owner and a clear set of actions. No guessing or forwarding emails into the void is needed because the distance between the warning and the employees’ ability to do something is shortened.

Looking ahead, the conversation will continue to evolve beyond traditional cyber response. Because in an AI-enabled enterprise, the new question is whether the data within those systems can still be trusted. When AI systems make decisions based on enterprise data, the attack surface becomes the data’s accuracy. A threat actor who quietly corrupts a dataset over 90 days before a recovery event has done more damage than just downtime. They can poison the inputs driving decisions across the business.

Regardless of how AI will change threat intelligence and cyber response, these principles remain the same. Know your problem, whether structural or technological. Ensure your human infrastructure keeps pace with your technical infrastructure, with clear cross-functional ownership and the tools and knowledge to act autonomously. Communicate with your boards often — and correctly.

Let’s not wait for the next headline to ask, “Are we ready?” Have those conversations now. Test your assumptions. Close your gaps. Because in today’s threat landscape, resilience isn’t IT’s job — it’s everyone’s mandate.

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Leadership wants to scale AI. Budgets are tripling. Adoption is up.

Then the CFO asks the question every board now asks: which of these initiatives is actually profitable?

Most organizations cannot answer that question, not because they lack visibility into cost, but because the cost data they have was never designed to produce that answer.

Applying lessons learned from managing cloud spend won’t be a fix for the AI and ROI quandary. True, cloud taught a generation of CFOs that billing without business context is noise. So to get cloud ROI, they stitched two data sources together: cost data plus business data. AWS reveals which account, which region, which tag, which resource. Merge in customer and product mappings on top and the ROI of the cloud spend comes into focus.

But AI is harder. It requires three data sources: cost, business, and telemetry—the automatic collection of data from disparate sources that helps to clarify the whole picture of what happened and why. An executive or engineering lead can have AI invoices and customer revenue. But they have no way to connect them to business value. The token count on the OpenAI invoice does not specify which customer triggered which call, which feature it served, or whether the prompt produced a business outcome. That data does not exist in the provider’s billing.

AI providers won’t fix this problem

The situation is not likely to change anytime soon because AI providers are not in the business of attributing an enterprise’s costs to that enterprise’s customers. Instead, AI providers are in the business of selling tokens. The granularity they expose is the granularity their billing systems require, not the granularity a CFO requires.

Not convinced? Compare what AWS gives you to what an AI provider gives you.

AWS billing exposes resource IDs, account hierarchies, region, SKU, tag metadata, usage by the minute. Every dollar can be attributed to a workload, a team, a customer segment if it was tagged correctly. The data is rich enough that mature FinOps teams built unit economics on top of it years ago.

An AI provider invoice gives you tokens consumed by model, with optional grouping by API key. That is the resolution. No request-level attribution. No customer ID. No feature mapping. No prompt outcome. No retry identification. Multi-step agent workflows collapse into a token count. Imagine a large bank receives a multi-million dollar AI invoice each month. But it has no visibility into what parts of the business were responsible for what parts of the cost so cannot allocate them.

If an enterprise wants to know what AI cost drove which customer or feature, it has to capture that data itself, inside an application, before the call leaves it. 

Three required sources

Building AI ROI measurement requires three data sources, stitched together in a single model.

1. Cost data, normalized across providers. Every AI provider delivers cost differently. OpenAI invoices in one taxonomy, Anthropic in another, fine-tuning vendors and inference platforms each in their own. Cloud GPU costs sit in AWS or Azure billing. Vector database costs land in Pinecone or Snowflake invoices. None interoperate by default. Normalization is necessary but not sufficient. It will put all your AI costs in one schema. It does not tell you what they produced.
2. Application-layer telemetry. This is the source most organizations are missing, and the one that makes AI ROI structurally different from cloud ROI. It requires instrumenting AI calls inside your application across six categories: request-level tracing tied to a customer or session ID; feature attribution tied to the product surface that triggered the call; agent-step capture for multi-step workflows; retry and fallback identification so recovery costs don’t get attributed to primary calls; model selection logging that records which model was chosen and why; and outcome capture that ties each call to whether it produced business value. None of this data exists in the provider’s billing. All of it has to be captured at the moment the call is made and stored in a system that can be stitched to the cost data.
3. Business data. Revenue, customer segments, product hierarchies, and feature usage. The same business data already feeding your CRM and analytics stack, mapped to the customers and features the telemetry layer attributes calls to.

Stitched together, the three sources produce the unit economics every AI investment decision now requires: cost per customer interaction, margin per feature, profitability per agent workflow, ROI per model choice. None of these can be calculated from billing data alone. None can be calculated from telemetry alone. They require all three sources, modeled together in a way that maps cost to outcome.

Why agentic AI makes this urgent

Single-call inference is the easy case. One request, one cost, one customer, one outcome.

Agentic workflows are different. An agent decomposes a task into multiple steps. Each step calls a model. Some steps fall back to a different model when the first fails. Some steps retry on a poor result. Some steps invoke external tools that themselves cost money. A single user request can produce dozens of inference calls across multiple providers, with the cost compounding in ways the provider invoice cannot disaggregate.

If telemetry does not capture agent-step granularity, no one will know which steps are profitable. Aggregate costs will show up three weeks later in the invoice. By then, the workflow has been running at scale, customers are onboarded, and unprofitable paths have been retried thousands of times.

When agents make the calls, the volume of cost-generating events without business context attached grows by an order of magnitude. The window for instrumenting this before it becomes unmanageable is closing.

What changes when the three sources come together

Once the three sources are stitched together, the AI investment conversation changes.

Five different ways to build the same AI capability stop looking equivalent. They converge on adoption metrics and diverge by 10x on cost. The team picks the approach that delivers a similar business outcome at one-fifth the cost, because the team can finally see the difference. Product teams design features with margin awareness from the architecture phase, not from the post-launch budget review. Engineering teams choose model architectures with cost-per-outcome data alongside latency and quality. Leadership evaluates AI initiatives the way they evaluate any other capital allocation: on unit economics, not on the engagement chart. Aggregated invoices track the cost per customer interaction. Engagement metrics reveal margin per feature. Gut-instinct model selection is checked against real cost-per-outcome model selection results. 

Within seconds, everyone can see which AI features are profitable, which should scale, and which should be killed. This is the insight everyone is looking for and companies that achieve it will optimize the benefits of AI.

The build trap

AI costs are compounding now. The board is not waiting 18 months for an internal project to reach production.

The temptation to build it anyway has never been sharper. AI coding tools have changed what a small engineering team can ship in a quarter. The instrumentation layer looks tractable. The cost normalization looks like a weekend project. The semantic model feels like something a senior engineer could draft over a sprint.

It is a trap. Three reasons.

Volume is the first. A production AI footprint generates millions of telemetry events per hour, and that volume scales with agentic adoption. Real-time ingestion, correlation, and attribution at that scale is not the same problem as vibe coding a prototype in an afternoon. It is a permanent operational system that has to be right every minute of every day.

The vendor landscape is the second. Cost data arrives in delayed billing windows from providers with non-interoperable schemas. Schemas change without notice. New AI providers enter the landscape monthly, each with its own taxonomy and metering. The system is not built once. It is maintained against a moving target that moves faster than most internal release cycles.

The third is what the first two add up to: this is business-critical infrastructure. The CFO and the board are going to make capital allocation decisions on the data this system produces. When schema drift goes unnoticed for two weeks, when an agent telemetry stream stops correlating to a vendor that quietly changed its billing API, the cost of being wrong is not a sprint of cleanup. It is a quarter of misallocated capital.

The build-vs.-buy question for engineering leaders has changed. It’s not “can we build this?” The honest answer is yes. The real question is whether the marginal hour of your strongest engineers is best spent stitching cost data to telemetry to business outcomes, or building the AI products that produce the revenue the cost data is measuring.

The capability is reproducible in weeks. The choice is whether to spend the next 18 months building it, or the next 18 months acting on it.

—

New Tech Forum provides a venue for technology leaders—including vendors and other outside contributors—to explore and discuss emerging enterprise technology in unprecedented depth and breadth. The selection is subjective, based on our pick of the technologies we believe to be important and of greatest interest to InfoWorld readers. InfoWorld does not accept marketing collateral for publication and reserves the right to edit all contributed content. Send all inquiries to doug_dineley@foundryco.com.

In public-sector and regulated-cloud work, I learned that sovereignty rarely starts as a national strategy. It starts as an auditor’s question: Who can prove where the data went, which system made the decision and what changes when the vendor or infrastructure does? That question is now moving into AI, and most sovereign-AI debates answer the wrong version of it.

They ask whether a country can build its own model on domestic data and hardware. For the United States and China, which together hold more than 90% of global AI data-center capacity, per a January 2026 Tony Blair Institute analysis, that question is worth asking. However, for almost every other government, it is the wrong place to start. The operative question is narrower: Once AI is embedded in public services, who controls the stack?

The 5 layers of public-sector control

For a CIO, sovereign AI means enforceable control across the AI lifecycle; model ownership is a separate question. Control has five layers:

• Data control: Where sensitive public data sits, and whether it can train a vendor’s model.
• Model control: Which models clear which workloads, and under what validation.
• Infrastructure control: Whether critical workloads run in approved environments.
• Operational control: Whether AI-assisted actions are logged, monitored and reversible.
• Vendor control: Whether the agency keeps portability, audit rights and a real exit.

Those five layers are the control plane for public-service AI. Floyd Dcosta recently made the enterprise case in “AI without sovereignty is just outsourced intelligence”: capability is what a tool can do; authority over how and when it does it is something a buyer can quietly lose. For public services, losing that authority plays out in the public eye.

Public-sector AI risk differs from enterprise risk. A retailer’s bad recommendation costs a sale; a government’s AI touches benefits, tax enforcement, policing and emergency response, raising the bar to due process, records retention and continuity of operations. A government that cannot reconstruct an AI-assisted decision lacks operational sovereignty, even in a domestic data center.

Evaluating risk: Concentration, jurisdiction and shadow AI

Foreign dependency is a real risk, but the exposure that matters is a sudden cutoff: A model you cannot audit, switch or exit, shut off by someone else’s order. A vendor’s nationality is a poor guide to that risk; control is.  Two markers matter. The first is concentration. In July 2024, a single faulty CrowdStrike update crashed about 8.5 million Windows machines, disrupting airlines, hospitals, banks and governments worldwide. No attacker was involved; one homogeneous dependency failed everywhere at once. The lesson points away from vendor nationality and toward uniformity as the fault line, making portability and provider diversity resilience controls.

The second is jurisdiction. In June 2025, Microsoft’s legal director for France told a Senate inquiry, under oath, that it could not guarantee that French public-sector data, even in French data centers, would be protected against US demands under the 2018 CLOUD Act. No such request had been made, and EU data has stayed in the EU since January 2025; senators called the assurance purely declarative. For the most sensitive data, residency does not equal control; the parent’s jurisdiction can matter as much as the server’s. Three US hyperscalers hold about 70% of the European cloud market, while European providers’ share fell from 29% in 2017 to roughly 15%. Concentration plus jurisdiction is the exposure a CIO must price. I have watched teams treat vendor selection as the moment risk was solved; it rarely was.

The wrong response is self-isolation. Most countries will never build frontier models, advanced chips, hyperscale clouds and talent pipelines at once; the Tony Blair Institute calls full self-sufficiency “too expensive, too slow and, for most countries, simply impossible.” The better test is workload sensitivity. Low-risk uses, such as drafting, translation and summarization, can run on commercial platforms with controls; high-risk uses, such as benefits eligibility, fraud investigation and healthcare triage, demand stricter control over data, model behavior and auditability.

Mandating domestic-only provision before a competitive option exists inverts sovereignty. Europe 2031, a five-year scenario from June 2026 by European technologists and policy researchers, illustrates the failure mode: A 2027 “buy European” mandate lands as offensive cyber capability spreads, and agencies that switched to weaker providers are locked out and paying ransoms. The scenario is fiction; the mechanism is not. Leverage comes from being indispensable, not half-hearted self-sufficiency. The closer-to-home effect is shadow AI: Mandate an inferior sanctioned tool and staff bypass it, the way shadow IT grows up around tools people find too slow. A rule that pushes sensitive work into ungoverned shadow AI reduces control instead of adding it.

Regulation and data-residency rules belong in any serious strategy, but carry failure modes. Blanket localization raises hosting costs and slows adoption without guaranteeing control, and a “sovereign cloud” on a foreign parent’s stack can amount to sovereignty theater. The more useful pattern tiers requirements by sensitivity. India’s BHASHINI shows the application layer done well: A public platform serving 100 million-plus inferences a month across 22-plus languages on a vendor- and cloud-agnostic design that keeps data and switching rights public. Sovereignty resides in the portability, not in a national model.

Building an operational sovereignty strategy

Public trust is the constraint sovereignty rhetoric tends to skip. The OECD’s 2025 review of government AI warns that opaque systems make AI-assisted decisions hard to explain and can give public servants false confidence in tools that fail quietly. State-controlled AI is the same problem from the other side: A government that deploys models against its own citizens without audit or record has gained control and lost accountability. An agency that can log, explain and reverse an AI-assisted action can defend it to citizens, courts, auditors and elected officials. If it cannot, it has bought access and called it sovereignty.

None of this is new. AI sovereignty repeats earlier fights over cloud, telecom, semiconductors and cybersecurity. Europe’s flagship cloud project, GAIA-X, became a cautionary tale; the Dutch technologist Bert Hubert called it an “expensive distraction” that produced no European cloud, the familiar result of ambition without absorptive capacity. Cloud taught governments that outsourcing infrastructure does not outsource accountability; telecom, that vendor dependency becomes strategic exposure; chips, that supply chains matter before a crisis; cybersecurity, that trust must be verified continuously. AI inherits all four at once.

Over the next five to ten years, some countries will build national platforms, more will build trusted cloud and trusted model regimes, and most will run hybrids that pair domestic data control with global model access. Trade policy will harden those choices: Export controls on compute and data-localization rules will pull the vendor market into blocs that track alliances more than open markets. For a CIO, that turns a vendor and hosting decision into a five-year bet on whose rules and supply chains will still hold. The ones that succeed will treat sovereignty as an operating requirement, backed by leverage, not a slogan. Start with the control plane before the model: Most agencies will never own the model, and the controls are what decide whether the AI they do run stays accountable. Even when procurement policy is dictated from above, these questions remain within the CIO’s authority:

1. Can we classify AI workloads by public-service risk?
2. Can we prove where sensitive data goes across training, retrieval, inference, logging and retention?
3. Can we restrict which models are approved for which data classes and functions?
4. Can we reconstruct an AI-assisted action in enough detail to explain it?
5. Can we change providers without losing continuity or institutional knowledge?
6. Can we explain the system to citizens, regulators, auditors and elected officials?

A “no” to any of these does not mean the agency lacks AI. It means the agency has access it does not yet control. Public institutions can use global innovation without surrendering public authority, but only once they know what to hold, what to rent and where dependency turns into risk.

This article is published as part of the Foundry Expert Contributor Network.
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Healthy software companies typically don’t suddenly eliminate one-fifth of their workforce, but monday.com is doing just that as it bets on flatter teams, AI agents, and customer implementation expertise as the winning combination in the AI era.

Monday.com co-founder and co-CEO Eran Zinman today announced the “very difficult decision” to reduce the AI work platform company’s global workforce by about 20%, or 620 people.

The move has nothing to do with increasing margins or replacing humans with AI, he insisted in his post on LinkedIn; rather, it’s a calculated decision to trim down and hone the company’s focus as AI becomes integral to day-to-day workflows.

“This is not a distress signal; it is a deliberate reset, disclosed with its price attached,” said Sanchit Vir Gogia, chief analyst at Greyhound Research. “The industry has quietly swapped the meaning of productivity, and this filing is the clearest exhibit yet.”

A ‘significant opportunity’ in technology

In a SEC filing this week, monday.com said its restructuring plan reflects the “ongoing transformation of its product, marketing, and go-to-market strategy.” The move is intended to support a “leaner, more focused operating model” as the company continues to invest in its AI-driven strategy.

Zinman noted in his post that the company has shifted to “doing the work with AI and not just managing it,” and is focused on building environments where “people and AI agents [work] together in one workspace.”

In recent months, monday.com has evolved its products, strategy, and the way it serves its customers, and Zinman contended that “the organization we built for our previous chapter is not the organization that fits the new AI era.” Monday.com needs to “execute more decisively,” take on new challenges, and quickly respond to market changes, he said.

“We have never seen such a significant opportunity in software, driven by such exciting technology,” Zinman noted. He emphasized that the reduction is not to replace people with AI, nor to improve margins; the “vast majority” of savings will be reinvested into talent, products, and AI.

The restructuring will result in a “flatter organization” with fewer management layers and smaller, more autonomous teams, and monday.com also has a new go-to-market model, Zinman explained. Customers expect “deeper implementation support” as they deploy AI, and the company will work more closely with customers, increase its on-site presence, create new roles, and “adapt many existing ones.” In its SEC filing, the company said it expects to continue hiring in “key strategic areas” throughout 2026.

Workers will be expected to work better, “not harder,” Zinman noted. He pointed to several past examples where work could have been done in a few days, but instead took many months with “multiple meetings and endless friction.”

“This wasn’t people’s fault and everyone was frustrated by this,” he said. “Our new org changes ownership to allow people to make decisions and move fast.”

A spokesperson for monday.com declined to comment further on the staff reductions.

Monday.com’s key market advantages

Monday.com certainly isn’t struggling; the company expects 19% to 20% year-over-year growth in 2026.

“Companies in that position do not restructure because they must,” Greyhound’s Gogia noted. “They restructure because they have decided to become something else.”

Melody Brue, VP and principal analyst at Moor Insights & Strategy, pointed out that organizational redesign is important for real AI transformation, but while it can signal confidence to the market, it can still be “devastating” to humans.

While the company looks as though it’s trying to do right, that ultimately remains to be seen, she said. “There are often hidden internal bruises that can surface long after layoffs.”

Monday.com’s advantage is in its “structured substrate,” Gogia noted; its boards, permissions and typed workflows give agents something firmer to act on than just documents and chat history. The company highlights its natively built agents that can be configured by any team member, as well as connectors with Claude, Microsoft Copilot, and ChatGPT, and dedicated routes for external agents to authenticate and operate.

“For some time, the sharper enterprise question has been shifting from who has an agent to who owns the governed runtime in which an agent can safely act,” he said. “Structured work is a serious claim on that runtime.”

But parts of monday.com’s agent estate remain in staged release, and its product is ultimately “mid-transition,” Gogia pointed out; its agent builder carried a beta label as recently as March,. Also, the company’s pricing model changed in May to a hybrid model charging for seats as well as mandatory AI credits. And, while its AI-powered no-code builder monday vibe passed $1 million in annual recurring revenue within two and a half months, monday.com has not released subsequent outcomes, usage volumes, or attach rates.

Further, there’s an element of “gravity” with its competitors, he observed. Asana is reorganizing teams around agents, Atlassian is wiring agents into the developer estate, and others are simply bundling them into their offerings: Microsoft is doing so across the productivity stack, and ServiceNow across enterprise operations, each with identity and procurement built in.

“Their pull is strongest exactly where monday.com wants to grow, in the largest accounts, where control-plane depth and administrative reach decide the deal,” said Gogia.

Actions for the near-term

Going forward, buyers should focus on operating risk, not headline risk, Moor’s Brue noted. In practice, that’s continuity of service, roadmap consistency, and strength of enterprise support. Productivity should be valued as better outcomes per unit of organizational effort, not mere activity.

“It should be a measure of how much smoother, faster, and more effective the operating model becomes when AI is built into the work,” said Brue.

Gogia noted that strain surfaces first in customer service, and monday.com’s attention is being redistributed. The company’s annual report disclosed that its focus is now concentrated on the largest accounts, with support for medium-sized clients moved to an AI-first and human-supported model.

During the first month of the transition, buyers should track named account continuity and escalation times, he advised. By the first quarter, keep an eye on whether credit governance and admin controls mature on schedule, and if the roadmap beyond the AI estate keeps pace. By the half-year mark, determine whether promised implementation depth is producing outcomes or “simply more billable engagement.”

Support tiers should be enumerated in writing before renewal, and buyers should contract for “side exits,” Gogia emphasized, with overage pricing fixed in advance, the right to pause consumption, and portability for workflows and agent configuration “if the relationship sours.” Finance should also insist on monthly consumption reporting by capability. Further, integration efforts, partner dependency, and change management should be considered first-class costs of the agent era, “not as afterthoughts to a license.”

“A license was a known cost,” said Gogia. “A meter is a behavior, and behavior is harder to forecast than headcount.”

This article originally appeared on CIO.com.

Healthy software companies typically don’t suddenly eliminate one-fifth of their workforce, but monday.com is doing just that as it bets on flatter teams, AI agents, and customer implementation expertise as the winning combination in the AI era.

Monday.com co-founder and co-CEO Eran Zinman today announced the “very difficult decision” to reduce the AI work platform company’s global workforce by about 20%, or 620 people.

The move has nothing to do with increasing margins or replacing humans with AI, he insisted in his post on LinkedIn; rather, it’s a calculated decision to trim down and hone the company’s focus as AI becomes integral to day-to-day workflows.

“This is not a distress signal; it is a deliberate reset, disclosed with its price attached,” said Sanchit Vir Gogia, chief analyst at Greyhound Research. “The industry has quietly swapped the meaning of productivity, and this filing is the clearest exhibit yet.”

A ‘significant opportunity’ in technology

In a SEC filing this week, monday.com said its restructuring plan reflects the “ongoing transformation of its product, marketing, and go-to-market strategy.” The move is intended to support a “leaner, more focused operating model” as the company continues to invest in its AI-driven strategy.

Zinman noted in his post that the company has shifted to “doing the work with AI and not just managing it,” and is focused on building environments where “people and AI agents [work] together in one workspace.”

In recent months, monday.com has evolved its products, strategy, and the way it serves its customers, and Zinman contended that “the organization we built for our previous chapter is not the organization that fits the new AI era.” Monday.com needs to “execute more decisively,” take on new challenges, and quickly respond to market changes, he said.

“We have never seen such a significant opportunity in software, driven by such exciting technology,” Zinman noted. He emphasized that the reduction is not to replace people with AI, nor to improve margins; the “vast majority” of savings will be reinvested into talent, products, and AI.

The restructuring will result in a “flatter organization” with fewer management layers and smaller, more autonomous teams, and monday.com also has a new go-to-market model, Zinman explained. Customers expect “deeper implementation support” as they deploy AI, and the company will work more closely with customers, increase its on-site presence, create new roles, and “adapt many existing ones.” In its SEC filing, the company said it expects to continue hiring in “key strategic areas” throughout 2026.

Workers will be expected to work better, “not harder,” Zinman noted. He pointed to several past examples where work could have been done in a few days, but instead took many months with “multiple meetings and endless friction.”

“This wasn’t people’s fault and everyone was frustrated by this,” he said. “Our new org changes ownership to allow people to make decisions and move fast.”

A spokesperson for monday.com declined to comment further on the staff reductions.

Monday’s key market advantages

Monday.com certainly isn’t struggling; the company expects 19% to 20% year-over-year growth in 2026.

“Companies in that position do not restructure because they must,” Greyhound’s Gogia noted. “They restructure because they have decided to become something else.”

Melody Brue, VP and principal analyst at Moor Insights & Strategy, pointed out that organizational redesign is important for real AI transformation, but while it can signal confidence to the market, it can still be “devastating” to humans.

While the company looks as though it’s trying to do right, that ultimately remains to be seen, she said. “There are often hidden internal bruises that can surface long after layoffs.”

Monday.com’s advantage is in its “structured substrate,” Gogia noted; its boards, permissions and typed workflows give agents something firmer to act on than just documents and chat history. The company highlights its natively built agents that can be configured by any team member, as well as connectors with Claude, Microsoft Copilot, and ChatGPT, and dedicated routes for external agents to authenticate and operate.

“For some time, the sharper enterprise question has been shifting from who has an agent to who owns the governed runtime in which an agent can safely act,” he said. “Structured work is a serious claim on that runtime.”

But parts of monday.com’s agent estate remain in staged release, and its product is ultimately “mid-transition,” Gogia pointed out; its agent builder carried a beta label as recently as March,. Also, the company’s pricing model changed in May to a hybrid model charging for seats as well as mandatory AI credits. And, while its AI-powered no-code builder monday vibe passed $1 million in annual recurring revenue within two and a half months, monday.com has not released subsequent outcomes, usage volumes, or attach rates.

Further, there’s an element of “gravity” with its competitors, he observed. Asana is reorganizing teams around agents, Atlassian is wiring agents into the developer estate, and others are simply bundling them into their offerings: Microsoft is doing so across the productivity stack, and ServiceNow across enterprise operations, each with identity and procurement built in.

“Their pull is strongest exactly where monday.com wants to grow, in the largest accounts, where control-plane depth and administrative reach decide the deal,” said Gogia.

Actions for the near-term

Going forward, buyers should focus on operating risk, not headline risk, Moor’s Brue noted. In practice, that’s continuity of service, roadmap consistency, and strength of enterprise support. Productivity should be valued as better outcomes per unit of organizational effort, not mere activity.

“It should be a measure of how much smoother, faster, and more effective the operating model becomes when AI is built into the work,” said Brue.

Gogia noted that strain surfaces first in customer service, and monday.com’s attention is being redistributed. The company’s annual report disclosed that its focus is now concentrated on the largest accounts, with support for medium-sized clients moved to an AI-first and human-supported model.

During the first month of the transition, buyers should track named account continuity and escalation times, he advised. By the first quarter, keep an eye on whether credit governance and admin controls mature on schedule, and if the roadmap beyond the AI estate keeps pace. By the half-year mark, determine whether promised implementation depth is producing outcomes or “simply more billable engagement.”

Support tiers should be enumerated in writing before renewal, and buyers should contract for “side exits,” Gogia emphasized, with overage pricing fixed in advance, the right to pause consumption, and portability for workflows and agent configuration “if the relationship sours.” Finance should also insist on monthly consumption reporting by capability. Further, integration efforts, partner dependency, and change management should be considered first-class costs of the agent era, “not as afterthoughts to a license.”

“A license was a known cost,” said Gogia. “A meter is a behavior, and behavior is harder to forecast than headcount.”

AI agents can turn a clear description into working software, the engineer’s judgement is what makes the difference: deciding what to build, catching the tradeoff the agent didn’t know to weigh, and owning the call on whether the result is right.

That judgement has always been the hard part of engineering. It just used to be bundled into the act of writing code, where a skilled engineer did it while typing. As agents take on more of the typing, that judgement separates out and becomes the clear center of the role. Leaders who adapt early will get their metrics, their talent pipelines, and their delivery models working with this shift rather than against it.

Judgement is defining, constraining, and deciding

Judgement is all about defining the problem precisely enough that an agent builds the right thing. It’s setting the constraints the agent won’t infer on its own. It’s spotting the tradeoff buried three layers down that only shows up if you understand the system. And it’s looking at a finished implementation and knowing whether it’s genuinely good enough to ship.

This is the harder part of the job and the real driver of quality. It was easy to underrate when it lived inside day-to-day coding. Now it’s what separates a strong team from an average one.

The shift changes where time, growth, and metrics go

If the high-value activity is intent, review, and judgement rather than raw output, a few assumptions are worth revisiting.

Where engineers spend their time. Less of the day goes to producing boilerplate and mechanical implementation, and more goes to the reasoning that used to get squeezed to the edges: framing the problem and owning the judgement calls that determine quality.

How teams grow their people. Defining problems well, spotting risk, and critically evaluating work you didn’t write yourself have always been senior skills. When agents handle more of the mechanical work, those skills become learnable earlier. That puts the emphasis on leaders to teach the reasoning: why a choice gets made and how to weigh the tradeoffs that come with it.

What you measure. Lines shipped, tickets closed, and velocity charts all measured throughput of the old scarce resource. They say very little about the new one. The teams that adapt will start measuring the quality of intent going in and the reliability of judgement coming out, because that’s where the results now live.

Reinvest the time you get back

The tempting response is to treat the freed-up capacity as pure speed: same work, same tooling, just faster. That captures the easy win and misses the real one. If engineers spend their reclaimed time reviewing a rising volume of agent output with no better context than before, review quietly becomes the new constraint, and you’ve moved the problem rather than solved it.

The organizations that get ahead will invest the reclaimed capacity into the judgement layer: creating stronger specs and acceptance criteria before work starts, building review practices that test agent output against intent, and capturing the reasoning behind decisions where the next person can find it, so it doesn’t have to be reconstructed every time. That’s how the shift becomes an advantage for your team.

The through-line for leaders

The engineering job is moving up a level, from executing the work to directing and validating it. That’s a more strategic role, and it rewards clarity of thought over speed of output. Leaders who see the shift early can help their engineers grow into the work that’s now most valuable.

See how leading engineering organizations are operationalizing this shift at jira.dev.

For many engineering teams, AI adoption means individual engineers write code faster while overall team velocity remains stagnant. Individual speed and team speed are produced by different things, and AI has mostly accelerated the first but not the second.

The step from individual AI adoption to team advantage is one many organizations haven’t taken yet, but it’s the step where real ROI lives. Make the leap and every individual gain starts compounding into something the whole team feels.

Faster individuals, but the same team pace

A developer with a good AI assistant can produce more and produce faster, but ten developers all doing that, each in their own way, with their own tools and their own context, don’t add up to a team that is ten times better. More often they add up to a team moving faster in ten different directions.

The speed stays with the person who created it. The reasoning, context, and decisions that the rest of the team would need to build on that speed gets lost.

These three structural problems explain why:

Problem #1: Context evaporates at scale

An engineer spends an hour with an AI agent working through a hard design decision. They land somewhere good. The code ships. But the reasoning, the alternatives they ruled out, and the constraints they discovered stay in a chat history nobody else will ever open. Six weeks later a teammate touches the same system, has no idea any of that thinking happened, and starts over.

You can’t prompt your way out of a context vacuum. Agents and teammates alike are only as good as the context they start with, and right now most of that context is being generated and immediately lost. The teams that pull ahead will be the ones that treat the reasoning around the work as something worth capturing.

Problem #2: Misalignment creates duplicative work

When individuals move fast in parallel without a shared source of truth, they start stepping on each other’s toes. Two people solve the same problem two different ways. An agent generates a change against a spec that quietly went stale last week. A confidently written pull request follows the wrong internal standard because the standard lived in someone’s head, not in the workflow.

This problem gets worse as more of the work becomes agent-driven. Agents overwrite each other. Specs drift out of date faster than anyone updates them. The faster the individual pieces move, the more expensive the collisions become.

Problem #3: Trust doesn’t scale

The quiet tax on AI-assisted work is review. If an individual developer can’t see how a piece of work was produced, what the intent was, what the agent was told, what standards it was working against, then they can’t confidently build on it. So, they re-check it, or rewrite it, or route around it. The individual saved an hour. The team spent two earning back the trust.

Trust transfers when intent is legible. When a teammate or a reviewer can see what was meant, what was decided, and what guardrails applied, they can accept the work and move on. When they can’t, every handoff becomes a re-litigation.

Turning adoption into advantage

The through-line across all three problems is the same. The value of AI at the team level does not live in the code any single person or agent produces. It lives in whether the intent and context around that work is captured, shared, and reusable by everyone else, human and agent.

That reframes the leadership job. It’s not about driving more adoption, because your teams already handled that. It’s about building the connective layer that turns individual output into team capability.

The window is now

This matters more every month, because the individual productivity story is about to become an agent orchestration story. The organizations that turn individual adoption into team advantage now, while the habits are still forming, will be the ones whose agents actually compound.

See how engineering leaders are building the connective layer between individual AI adoption and team-level compound returns at jira.dev.

Your CFO has a simple question. “We’re spending more on AI. What are we getting for it?” Most CIOs cannot answer it — not because AI isn’t creating value, but because the accounting systems we inherited were built before AI existed as a category of labor.

This June, the conversation shifted from token maxing to token cutting. The New York Times reported that Meta, Uber, Walmart and Amazon are capping employee AI usage. Uber blew through its 2026 AI budget in four months. Satya Nadella started framing it as human capital versus token capital.

All of that is true. None of it answers the CFO. Capping tokens is an input lever, not an output measure. And the human-versus-token framing names two sources of labor when the reality is four.

The enterprise now has 4 sources of labor

There are humans. There are humans assisted by AI. Humans are working alongside AI. And humans are managing AI. Sources two through four are all supervised machine labor at different intensities — none of them have a line item, a manager or an hourly rate. In our 2026 AI Labor Report, 78% of leaders view AI as both software and a labor force. The org chart has not caught up. Neither has the P&L.

Lexi Reese

Most enterprises are stuck at A-Level 1 with no accounting for any of it, while quietly sliding into A-Level 2. The job descriptions have not caught up. The budget has not caught up. You cannot upskill into a role that has not been named.

AI is the only category of work the modern enterprise has ever bought without a system of record for what it produced.

What you are actually running is supervised machine labor

The model does a first pass. A human makes it usable. One hundred percent of leaders we surveyed said AI work requires human review before it ships; 34% said substantial editing. That is a workforce with no manager, no hourly rate and no line on the income statement.

The accounting breaks in 3 places at once

Under GAAP: COGS if it helps produce the product, OpEx if it does work for you. The same workflow can hit all three buckets at once. A tier-one support resolution involves the human’s salary (OpEx), the AI’s tokens (COGS if support is a delivered service), and the supervisor’s review time (OpEx). Three buckets. One piece of work. No reconciliation. The token invoice arrives from Anthropic or OpenAI and gets coded to OpEx-software because that is what the bill looks like. Audit partners will be asking about this by next year.

When you call AI a tool, you book it like software. When you call it labor, you have to ask which kind and what it is producing.

The per-employee number is the wrong unit

Per-employee AI spend collapses a workforce into a per-head average. It hides the only number that matters: What AI is producing inside each workflow.

Lanai measured two teams inside the same finance organization. Same monthly prep and variance analysis. AI took the same amount of time to produce outputs of similar quality. The only variable was the model each team reached for by default — a choice nobody had made deliberately and nobody had seen until it was measured.

Lexi Reese

The gap existed for months before anyone saw it.

Faith-based budgeting — the organizational equivalent of putting money in the collection plate and hoping God handles the ROI — is what made it invisible.

Lexi Reese

AI labor orphaning

That is not a measurement problem. It is a category error. We call it AI Labor Orphaning. AI does the work. The output gets credited to the human who approved it. The token bill lands in OpEx-software. The supervision time absorbs into salaried hours nobody is auditing. Eighty-seven percent of leaders admitted AI output is sometimes or always credited entirely to the human employee. This is the last-click attribution problem of the AI era, running in reverse.

What fills the vacuum? Belief. Forty-three percent assume that if AI was involved, it contributed. Only twelve percent have a clear methodology. Seventy-nine percent are worried AI budgets will be cut because they cannot connect spend to results. The cuts are not coming because AI does not work. They are coming because nobody can prove that it did.

Capping tokens may look like responsible governance, but it is like turning off a staticky radio rather than tuning the dial. The companies cutting AI budgets in 2026 will discover in 2027 that they cut the workflows that worked alongside the ones that did not.

The real cost of AI is not the model. It is the redesign

Three layers. Most organizations only manage the first.

Lexi Reese

What to actually do

The 12% of organizations that can answer the CFO treat AI like every other category of labor — with a cost per AI Work Hour that is accounted for by a set of AI assistants, co-pilots and agents that are held accountable to performance standards. 

• Audit the four sources separately. Each A-Level has different token economics, SaaS implications and human redesign requirements.
• Find the embedded SaaS repricing before your next renewal. Pull your top 20 contracts. Ask whether AI features previously included are now priced incrementally.
• Redesign the human role at A-Level 2 before you scale it. You cannot upskill into a role that has not been named.
• Build a system of record before you build the next agent. Start with one department. Two weeks. You will find something that surprises you.
• Stop calling it a tool. Start calling it labor. The language determines the chart of accounts.

When your blended AI rate is $22 an hour, the conversation shifts from ‘we spent $340,000 on AI’ to ‘we acquired a skilled workforce at $22 an hour.’ That sentence is defensible. A vendor invoice is not.

The CIOs who will have a defensible AI story in 2027 are the ones who renamed the work in 2026. Not because technology changed. Because they finally built the accounting to see it.

Findings are drawn from the 2026 AI Labor Report, fielded by Wakefield Research with 200 senior technology leaders at US enterprises of 1,000-plus employees, March 20–April 8, 2026 (±6.9pp at 95% confidence).

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In a single month, one enterprise reportedly spent half a billion dollars on AI. A consultant told Axios that the client had handed its workforce AI licenses, set no usage limits and let the meter run until finance noticed. The figure is spectacular, and it is the wrong thing to fear. That half-billion-dollar accident is only the visible part of a quieter, far larger failure. Worldwide AI spending is forecast to reach $2.52 trillion in 2026, more than any technology category in a generation, and by the most cited measure, roughly 95 percent of it returns nothing. Boards read that as proof that the technology does not work. The evidence points somewhere less comfortable, and it is not a technology problem at all. Most boards cannot see it because they are reading the wrong number: They track failure when the number that matters is allocation. The discipline that separates the winners is not technical. It is how they allocate capital across time, and how willing they are to stop. The hardest discipline in the AI era is not adopting faster. It is allocating honestly and refusing to judge a three-year bet on a six-month cycle.

The number everyone quotes, and no one acts on

The headline statistic is now familiar. MIT’s Project NANDA, in its 2025 study The GenAI Divide, found that about 95 percent of enterprise generative AI pilots produced no measurable impact on the P&L, while roughly 5 percent captured nearly all the value. S&P Global Market Intelligence found that the share of companies abandoning most of their AI initiatives jumped from 17 percent to 42 percent in a single year, with the average organization scrapping 46 percent of its proofs-of-concept before production. Gartner expects more than 40 percent of agentic AI projects to be canceled by the end of 2027, citing escalating costs, unclear business value and inadequate risk controls. And the pattern predates generative AI: RAND found that more than 80 percent of AI projects fail, roughly twice the rate of comparable work that does not involve AI.

Read as a technology story, these numbers say AI does not work. Read correctly, they say something more useful. MIT’s own authors located the cause not in model quality but in a learning and integration gap. The winners were not running better models. They picked one problem, executed and worked well together. Purchased solutions reached production about 67 percent of the time, while internal builds succeeded roughly a third as often. Gartner’s own spending forecast notes the same pivot, with CIOs scaling back ambitious internal builds in favor of commercial solutions that promise more predictable value. None of that is a verdict on the technology. It is a verdict on allocation: What gets funded, for how long and against which yardstick. The popular prescription, heard in every boardroom this year, is to measure harder and prove value sooner. That advice quietly repeats the mistake, because forcing a three-year bet to prove itself sooner is precisely how you kill it. The fix is not more measurement. It is measuring each bet against the right clock and subtracting the ones that miss.

The six-month cycle problem

Return to that 95 percent, because the way it is measured is the whole argument. Much of the reported failure is judged on a short clock, with a pilot counted as a failure if it has not shown a measurable financial return within roughly six months. The single most quoted number in enterprise AI is therefore a six-month yardstick applied to every initiative, including the bets designed to pay back in three years. The headline failure rate is not only a measure of AI. It is a measure of impatience.

The most expensive mistake in enterprise AI is a timing error. Enterprises have been spending heavily on AI for more than two years, and 2026 is the year boards are demanding returns. The multi-year bets funded during the 2024 and 2025 scale-up are only now far enough along to be judged. When a board reviews an initiative, it applies the yardstick it knows, which is quarterly return. That yardstick is correct for an efficiency project and ruinous for a capability bet. A workflow automation that should pay back in two quarters and a foundational data and agent capability that pays back in three years are not the same instrument, yet they are reviewed in the same meeting against the same metric.

This is the heart of the divide. The 5 percent did not simply pick better projects. They judged each project against its own horizon. McKinsey’s enduring Three Horizons model made this discipline standard in corporate strategy a generation ago: near-term, emerging and long-term bets are funded and measured differently. AI erased that discipline because the hype compressed every timeline into the current quarter. The result is two failure modes that appear opposite yet share a common root. Organizations kill three-year bets at month six because they miss a metric the bet was never designed to hit. And they keep funding six-month theater for years because it is visible, safe and never asked to prove a return. Both are allocation failures. Neither is a technology failure.

Subtraction is a strategy

There is a second discipline, the 5 percent share, and it is the one boards find hardest. They subtract. Every credible study of the failure rate describes the same chaotic pattern underneath it: Initiatives are abandoned late, without criteria, after the money is spent and the credibility is gone. Disciplined organizations do the opposite. They decide the conditions for stopping before they start, and they stop on schedule. Subtraction is not the absence of strategy. It is the strategy. Capital removed from a failing bet is capital available for a surviving one, and the survivors are where the entire return lives.

This reframes the 42 percent abandonment figure. Abandonment is not the problem. Undisciplined abandonment is. An organization that liquidates a position the moment it breaches a pre-agreed kill line is practicing portfolio hygiene. An organization that lets a doomed pilot run until someone loses patience is paying full price for a lesson it could have bought at a discount. The 5 percent who won were not smarter. They were patient in the right places and ruthless in the wrong ones.

The HALT framework: Horizon, Allocation, Liquidation, Tracking

Treating AI as a portfolio rather than a pile of pilots requires four disciplines, and the organizations that execute well put all four in place before the next funding cycle, not after the next failure. The name is deliberate. The discipline most enterprises lack is the willingness to halt the wrong bets in time to fund the right ones.

Component 1: Horizon. Classify every AI initiative by its true payoff horizon before it is funded. Horizon 1 covers efficiency plays that should return value within two quarters. Horizon 2 covers capability bets, data foundations, agent platforms and integration work that pays back in roughly 6 to 18 months. Horizon 3 covers transformation bets that take eighteen months to three years or longer. Each horizon carries its own success metric, set at funding time. A Horizon 1 yardstick never judges a Horizon 3 bet. This single rule prevents the most common and most expensive error in the portfolio.

Component 2: Allocation. Decide the split across horizons deliberately, as a board-level capital decision, not as the accidental sum of whatever pilots happened to win approval. A practical reference point, borrowed from decades of innovation-portfolio practice, is roughly 70% to near-term value, 20% to capability, and 10% to transformation. The exact ratio is yours; the discipline is to choose and defend it. The failure mode is an unmanaged portfolio: 90 percent scattered across disconnected Horizon 1 experiments, with nothing compounding into the Horizon 2 capability that the buy-and-integrate winners actually built.

Component 3: Liquidation. Attach a kill line to every initiative at the moment it is funded: A named milestone, a date and an owner empowered to stop it. If a bet misses its horizon-appropriate milestone, it is liquidated, and capital is reallocated on schedule without debate over sunk costs. The absence of a pre-agreed kill line is not patience. It is an unpriced liability that the board has almost certainly not been shown.

Component 4: Tracking. Report the portfolio to the board on a fixed cadence using a single instrument: The AI Portfolio Scorecard. Not a deck of project updates, but a single view of allocation by horizon, burn against milestone, liquidation decisions taken and capital reallocated to survivors. The cadence is the control. A portfolio reviewed once a year is a portfolio managed by hope.

THE AI PORTFOLIO SCORECARD: SCORE EVERY INITIATIVE BEFORE IT IS FUNDED

Score each criterion: 0 = not present, 1 = partially documented, 2 = fully verified. Total out of 12. Bands: 0 to 4 = DO NOT FUND  |  5 to 8 = CONDITIONAL  |  9 to 12 = FUND.

THE LIQUIDATION GATE: RUN AT EVERY BOARD REVIEW BEFORE CONTINUING FUNDING

Any unresolved FAIL = stop funding, liquidate the position, reallocate the capital to a survivor and record the decision on the scorecard.

The cost of the timing error

The financial case follows the pattern and is consistent. Consider two organizations that funded the same class of Horizon 3 bet: A domain-specific agent platform meant to compound over three years. The first review was conducted at month six against a quarterly return test, found no payback and killed it, booking the write-off as a lesson about AI being overhyped. Its competitor classified the same work as Horizon 3, set an 18-month capability milestone, protected funding through two review cycles and shipped to production within the window the work actually required. One organization spent its money to learn that it lacks allocation discipline. The other spent comparable money and now owns a capability its rival has abandoned and cannot quickly rebuild. The dollars on the two income statements are similar. The competitive positions are not.

The governance return the board has been waiting for

Allocation discipline does two things at once. It stops the bleed by liquidating failures on a schedule rather than at the point of exhaustion. And it concentrates capital where the entire return lives, in the small number of bets that survive their horizon. The 5 percent figure is not a ceiling imposed by the technology. It is the current yield of an industry allocated by hype. An organization that classifies by horizon, allocates on purpose, liquidates on a line and tracks on a cadence is not trying to beat the technology. It is trying to beat its own indiscipline, and that is a far more winnable contest.

The board conversation about AI returns is coming for every organization, and it arrives the moment the spending outpaces the story. When it does, the CIO will be asked a simple question: Where did the money go? The leaders who can answer will not show a pile of pilots. They will show a portfolio: What was funded, against which horizon, what was liquidated and when, and what the survivors are now worth. Subtraction is a strategy. The only question is whether you are practicing it on purpose or about to learn it by accident.

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For the past three years, the AI conversation has been dominated by scale. Bigger models, bigger compute clusters, bigger headlines. But the next wave of competitive advantage won’t come from who can rent the biggest model; it will come from who can build the smallest one that knows their business.

That model is the small language model (SLM): Compact, purpose-built, trained on an organization’s own data and run under that organization’s own governance. And it is about to become one of the most consequential strategic assets available to both the private and public sector.

The problem with renting intelligence

Right now, most organizations consume AI the way they once consumed electricity from a single utility by plugging into a handful of frontier models built by a small number of global vendors. These models are extraordinary generalists. They are also, by design, generic. They are tuned to be safe, broad and useful to everyone, which means they are optimised for no one in particular.

That’s a problem for any organization trying to build genuine differentiation. If every competitor in your sector is calling the same foundation model with the same prompts, the model itself is not your edge. Your edge is what only you know, your proprietary data, your institutional judgement, your operating history. A generic model can’t see any of that unless you keep feeding it to them, turn after turn, at cost, with no lasting memory and no guarantee of where that data ends up.

An SLM flips that equation. Trained on an organization’s own document libraries, case histories, policy archives, transaction data and operational know-how, it becomes a model that thinks the way your organization thinks, because it was built from your organization’s accumulated judgement. It doesn’t need to be the smartest model in the world. It needs to be the most useful one for you.

I’ve seen this play out directly. At one of Australia’s largest integrated tourism and cruise businesses, simultaneously a B2C retailer, a B2B distributor to thousands of agency and wholesale clients globally, an aggregator marketplace for more than 1,800 independent tourism operators, and a cruise operator with offshore shared services spanning finance, customer contact and content management. The constraint wasn’t a lack of access to large general-purpose models. It was that none of them understood the business: 1,800 different operator catalogues, each with its own pricing logic, inventory quirks and content conventions; years of customer contact history with its own vocabulary and escalation patterns; a marketplace search experience that needed to reason over the business’s own product taxonomy, not the open web’s.

Models trained and tuned on that proprietary data, operator listings, historical tickets, booking and pricing data delivered results a generic model never could. Domain-tuned content drafting cut operator listing time by 70% and eliminated a 23-day onboarding backlog outright, taking new-operator time-to-live from 23 days to three. A semantic search model trained on the marketplace’s own product catalogue lifted booking conversion by 24%. AI-driven triage trained on the business’s own contact history cut Tier 1 escalations by 34%. None of this came from a smarter foundation model. It came from a smaller, more specific one that knew the business.

Why “small” is the strategic choice, not the compromise

There’s a temptation to treat SLMs as the budget option, what you build when you can’t afford a frontier model. That’s the wrong frame. The evidence is already compelling: Microsoft’s Phi-4 family of small models, released in early 2025, demonstrated that a 14-billion-parameter model can match or exceed the performance of models many times its size on complex reasoning and domain-specific tasks while running at a fraction of the compute cost and on-premise, entirely within an organization’s own infrastructure. Smaller, domain-trained models are increasingly outperforming general-purpose giants on narrow, high-value tasks, with far tighter control over data residency, security and explainability.

For a CIO or CTO, that combination of lower cost, tighter governance, higher task-specific accuracy is rare enough to demand attention on its own. But the deeper value sits one layer up, at the operating model. An SLM trained on your service history can sit inside claims processing, citizen services, clinical triage, asset maintenance scheduling or M&A due diligence quietly compounding institutional knowledge into a reusable asset rather than letting it walk out the door every time someone retires or resigns.

That is the real shift: AI capability stops being a subscription and starts being a balance-sheet asset. It can be valued, protected, audited and improved because it belongs to you.

The public sector’s hidden advantage

Nowhere is this more obvious than in government. The public sector sits on some of the richest, least-exploited data and institutional knowledge in the country: Decades of policy outcomes, service delivery history, regulatory precedent, infrastructure records and frontline expertise. Most of it has never been put to systematic use because no commercially available model was ever trusted to touch it, and rightly so.

A small, sovereign, purpose-built model changes that calculus. Trained, hosted and governed entirely within government infrastructure, an SLM doesn’t require sensitive citizen or policy data to leave a secure perimeter. The Australian Government has already recognised this direction: The APS AI Plan, released in November 2025, commits to expanding the GovAI platform to provide all public servants with secure, sovereign AI tools operating entirely within Australian Government infrastructure. SLMs tuned to individual agency mandates are the logical next step and a more powerful one than any generic government-wide tool can deliver.

Rather than each agency independently negotiating with the same handful of overseas vendors, a coordinated approach of common standards for model governance, shared security architecture, common evaluation frameworks and pooled infrastructure investment would let agencies build and reuse SLM capability horizontally, the way shared services and common ICT platforms have been built before. Each agency gets a model genuinely tuned to its mandate, but the security model, audit trail and assurance framework are consistent, government-backed and independently verifiable.

Done well, this isn’t just an efficiency play. It’s a sovereignty play. As GovTech Review has noted, large language models hosted offshore create data flows that extend beyond Australia’s borders in ways that are rarely transparent, a risk that is simply untenable for government. Sovereign, purpose-built models keep Australian public data, public knowledge and the resulting capability uplift inside Australian hands, rather than exporting both the data and the long-term value to offshore platforms.

Why this belongs in the innovation budget, not the IT budget

The instinct in many organizations is to treat AI spend as an IT line item, something to be minimised, benchmarked and squeezed for cost efficiency. SLMs deserve a different treatment. They are closer to R&D than infrastructure: An investment in converting accumulated institutional knowledge into a durable, defensible capability.

That argument holds in the private sector too. A PE-backed portfolio company, a regulated financial services firm, a healthcare provider — each has years of proprietary operating data sitting idle in case files, transaction logs and service records. An SLM built on that data is a way of turning a sunk cost, decades of operational history, into a forward-looking asset that compounds with every additional case it processes.

Boards and executive committees that are still asking “what is our AI strategy?” as a single, undifferentiated question are asking the wrong thing. The better question is: Which parts of our operation are rich enough in proprietary data and judgement to justify owning the model outright, rather than renting someone else’s?

The opportunity in front of us

The first wave of enterprise AI adoption was about access: Getting a capable model into people’s hands quickly. The next wave will be about ownership: Who controls the model, who controls the data it was built on, and who captures the long-term value of the institutional knowledge it encodes.

Australia, with a public sector rich in data and a private sector with deep vertical expertise in financial services, resources, healthcare and logistics, is well placed to lead on this if it treats small, sovereign models as a genuine national capability question, not a procurement footnote. The organizations, and the country, that move early will not just save money. They will own something their competitors can’t easily replicate: An AI that knows them.

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Something interesting happened during an internal evaluation of AI meeting transcription tools at Tungsten Automation. The products worked. They weren’t bad. But sitting across from the pricing, we kept asking the same question: what exactly are we paying for?

We already had a secure enterprise AI environment. Building a meeting summary workflow took days, not months. We customized the outputs, injected our own internal context, and controlled security our way instead of working around someone else’s roadmap. We built it. It works better. We own it.

That’s not a knock on those vendors. It’s a signal of something more fundamental happening across enterprise software.

The moat was never the product

For two decades, SaaS rode a favorable asymmetry: building internal tools was hard, integrations were messy, and even modest automation required developers and long timelines. Buying was faster and cheaper than building. That asymmetry fueled the explosion of SaaS into every corner of the enterprise stack.

AI is collapsing that asymmetry. Large language models and agentic workflows can orchestrate APIs, move data between systems, generate interfaces, and automate business logic with a fraction of the engineering effort required even two years ago. The integration friction that once protected entire product categories is evaporating.

The vendors most exposed are not the deeply embedded enterprise platforms. They’re the lightweight workflow layers, the products that essentially put a polished interface on top of accessible data and relatively straightforward processes. Reporting dashboards. Meeting tools. Narrow productivity applications. These products created value by simplifying implementation. That rationale is getting harder to sustain when implementation is no longer the real barrier.

Here’s the part most analyses miss: it’s not just that AI makes development faster. It’s that agents change the integration model entirely. For 30 years, enterprise software was built for humans navigating UIs. Agentic systems don’t use UIs. They call APIs, read from multiple sources simultaneously, and move data freely across systems. The switching costs that once made incumbent software sticky are collapsing, because an agent doesn’t care which UI it used last quarter.

The SaaS that survives

The question isn’t whether SaaS survives. It’s which SaaS survives.

The companies with durable positions are not the ones with the cleanest interface. They’re the ones that transfer operational risk customers genuinely cannot absorb themselves. Compliance. Regulatory certification. Accumulated domain expertise. Liability.

Think about compliant invoicing across 140 countries. That’s not a workflow someone builds in a sprint. The certifications alone take years. A single regulatory change in one jurisdiction can break an AP process for a global enterprise overnight. Customers don’t pay for that capability because it’s technically complex. They pay because they cannot afford to own the risk of getting it wrong.

That’s the distinction that matters: AI lowers the cost of building software. It does not lower the cost of absorbing risk. The vendors who understand this are building durable businesses. The ones who don’t are quietly subsidizing their customers’ internal build programs.

Software sells features. Platforms sell accountability.

The prototype trap

The danger for enterprise buyers right now is overcorrection. Every successful prototype looks like a cost-saving opportunity. Very few survive the jump to production.

Building a workflow with generative AI is becoming straightforward. Maintaining it is not. Models evolve. Outputs drift. Governance requirements tighten. What worked cleanly in a controlled environment behaves differently at scale, and the failure mode is worse than traditional software. Rule-based automation, when it fails, fails obviously. Agents fail silently, confidently, at scale, often with a completely reasonable-sounding explanation.

Engineering teams that take on AI-powered systems need to solve for observability, model drift, access controls, audit trails, and long-term maintenance ownership. In regulated industries, they need to demonstrate exactly how the system reached every decision. That’s not a weekend project. That’s an ongoing operational commitment that compounds over time as models change and regulatory requirements evolve.

Before a team decides to replace an external platform with internal AI tooling, the honest question isn’t, “Can we build this?” The real question is, “Are we prepared to own this in production, for years, as the underlying models change beneath us?” Sometimes the answer is yes. Often the answer is no, and the true cost only becomes visible after the vendor contract is canceled.

Build vs. partner: a sharper frame

The build vs. buy framing has always been too binary. The right question is build vs. partner.

Partner for the capabilities where risk transfer, regulatory complexity, and domain expertise create genuine value your team cannot replicate. Build for the capabilities that actually differentiate your business from your competitors. Don’t burn your best engineers rebuilding compliant invoice processing or production-grade document extraction. Those aren’t competitive advantages. They’re table stakes, and someone else has already paid the cost, across decades, to make them reliable.

The organizations getting this right are honest about where they create unique value. They focus development there, and partner for everything else. The ones getting it wrong are vibe-coding solutions to non-differentiating problems while their actual competitive moat goes unattended.

The true value of software

We’re not watching the death of SaaS. We’re watching the end of the friction-based value proposition: the idea that software is worth renewing because integration used to be painful. That rationale is largely gone.

What survives is software that does something customers cannot reasonably replicate internally: absorb risk, maintain regulatory compliance, deliver operational reliability at scale, and bring genuine domain expertise into a production-grade system that someone else already stress-tested for years.

The vendors who recognize this are already repositioning around accountability, governance, and outcomes. The ones who haven’t will find the next renewal conversation noticeably harder.

Software sells features. Platforms sell accountability. That distinction is about to separate a lot of winners from a lot of cautionary tales.

—

New Tech Forum provides a venue for technology leaders—including vendors and other outside contributors—to explore and discuss emerging enterprise technology in unprecedented depth and breadth. The selection is subjective, based on our pick of the technologies we believe to be important and of greatest interest to InfoWorld readers. InfoWorld does not accept marketing collateral for publication and reserves the right to edit all contributed content. Send all inquiries to doug_dineley@foundryco.com.

Attackers are increasingly using AI agents to automate all phases of cyberattacks, prompting the security industry and enterprises to find new network defense approaches. One technique that shows promise is to intentionally plant decoy files with prompts that trigger the content safety guardrails built into LLMs with the goal of crashing rogue agentic workflows.

Using decoy resources as tripwires that alert defenders about potential unauthorized access is not a new idea in cybersecurity. These are known as canaries — after the canary in the coal mine early warning system — and can be fake documents, AWS access keys, database dumps, DNS records, and even URLs that would not be queried by legitimate processes, but would be attractive targets for attackers.

What’s new in the approach devised and tested by security firm Tracebit is to use these decoy resources not merely to trigger alerts, but to actually stop AI agents, buying defenders more time. Dubbed “context bombing,” the technique takes advantage of the fact that LLMs are inherently vulnerable to prompt injection — acting on instructions they might encounter inside the data they process.

Enterprises that build their own AI agents have to worry about malicious prompts placed by attackers on web pages, emails, documents, code comments, and in other third-party resources those agents might access. With no defenses in place, companies risk their own agents being hijacked and used against them to perform unauthorized actions. But the malicious AI agents used by attackers have the same vulnerability.

“We call the defensive version a context bomb: a short piece of text designed to trigger a model’s safety guardrails, planted directly in the attacker’s path — a decoy secret, environment variable, or DNS record,” Sam Cox, Tracebit’s CTO, said in a blog post. “An AI agent that reads it will frequently refuse to continue. You still get the alert; and the attack now halts early instead of merely being detected.”

Context bombing triggers massive drop in attack success rate

Tracebit’s tests performed in an AWS test environment cut the success rate normally achieved by AI models across multiple attacks paths by up to 90% by simply adding instructions that would trigger their content safety guardrails. LLMs are trained to refuse answering questions about creating biological, chemical, or nuclear weapons, or, in the case of Chinese open-weight models, sensitive political topics such as the Tiananmen Square massacre.

Furthermore, once one of these banned instructions make it into the context window, the whole session is poisoned, and the model will often refuse to continue without manual intervention. The researchers ran many tests to find short strings that would trigger model safety guardrails reliably, but it’s worth noting that the identified strings were different between the tested models: Claude Opus 4.8, Gemini 3.1 Pro, GLM 5.2, DeepSeek V4 Pro, and Kimi K2.6.

During baseline tests the AI agents managed on average to obtain full account admin in 54% of the 154 attack runs and full compromise (admin + persistence) in 36% of tests. With the context bombs in place, their success rate dropped to 5% for admin access and 1% for full compromise. Also, in 91% of baseline attack runs, the agents managed to complete at least one of ten possible attacks paths, but their average success rate dropped to 15% with the context bombs.

The models from Western AI labs — Opus and Gemini — proved the most capable at reaching full admin access, with 93% and 70% success rates, but were also the most impacted by the context bombs with both their success rates dropping to 0%. This shows that the content safety guardrails are much stronger in these models compared to the Chinese ones that were tested.

Attackers experimented with safety refusals first

The Tracebit researchers had already been experimenting with AI canaries for alert purposes. A paper published in May showed that canaries alerted defenders in 95.9% of 162 successful attack runs performed with AI agents using 10 different AI models. The alerts were triggered 8 minutes before the agents performed critical actions, while the runs required 14 minutes on average to reach admin access.

During those tests the researchers observed that if they instructed the models that the network might include deception, their success rate for full admin access and persistence dropped from 20% to 3% on average.

Then in June, researchers from security firm Socket.dev came across a software supply chain attack involving malicious PyPI wheels that contained prompt injections with content designed to trigger safety guardrails inside AI models. The malicious prompts were included in code comments at the start of the files and the purpose was likely to evade detection from LLM-powered security scanners.

“This header appears designed for AI-mediated analysis, not for Node, Bun, or Python,” the Socket.dev researchers said at the time. “It attempts to derail scanners or analyst copilots that feed the beginning of a file to a language model without clearly isolating the content as untrusted data. In weak pipelines, this can cause refusal behavior, prompt confusion, context pollution, or premature classification before the scanner reaches the actual malware.”

The Tracebit researchers then had the idea to flip the script and trigger such safety refusals through their canary technique against malicious AI agents. So not only does the agent run stop, but an alert is also triggered because the canary was accessed.

There is a risk that the canaries could also be discovered and accessed accidentally by legitimate LLM-powered tools used by engineering or security teams. But at the same time this means organizations could potentially deploy such canaries in sensitive places to stop their own AI agents that might become hijacked or go off the rails on their own.

There are many reports online where AI models performed destructive or unauthorized actions like deleting databases and folders or elevating their privileges because they got struck in failure loops and explored creative ways to complete their tasks. This is even more common with autonomous AI agents that are tasked to reach a goal without human intervention or supervision.

“The speed of autonomous AI attacks is why deception is climbing the priority list for security programs,” Tracebit’s Cox said. “When the attack chain takes minutes rather than days, every minute of response time you can claw back matters — and a control that stops the attacker outright, rather than just reporting them, changes the economics significantly.”

Last year Anthropic gave away one of the most successful things it has ever built. And, no, I’m not talking about Claude. I’m referring to MCP, the now ubiquitous Model Context Protocol, which Anthropic donated to the Linux Foundation’s new Agentic AI Foundation⁠. At the time, MCP was pulling nearly 100 million monthly SDK downloads across more than 10,000 active servers⁠, prompting the question as to why any company would give up such a popular piece of technology.

Google did much the same months earlier, handing its Agent2Agent (A2A) protocol to the Linux Foundation⁠ with AWS, Cisco, Microsoft, Salesforce, SAP, and ServiceNow signing on as founding members. OpenAI, not to be outdone, supports remote MCP servers in its Responses API⁠, sits on the MCP steering committee, and contributed AGENTS.md to that same foundation alongside its fiercest rival’s protocol.

It’s like Game of Thrones, except the principal AI powers seek regime change through seeming acts of beneficence rather than violence. For those who have been around for a while, it’s also entirely predictable, following a similar script we’ve seen in the cloud, on-premises servers, and more. Platform companies don’t give away technologies they’ve stopped caring about. They give away technologies they no longer need to own because competitive advantage has shifted to new ground.

What does this mean for AI?

Gravity has shifted before

Google has long been an exceptionally active contributor to open source. As I wrote in 2017, Google wasn’t open sourcing TensorFlow and Kubernetes out of generosity but rather turning these open source assets into on-ramps for Google Cloud. Google was playing catch-up to AWS and Microsoft. As then Google product manager Martin Buhr said, the company hoped to “create a gravity well in the market for container-based apps [so] that a significant percentage of them will end up with us.”

In other words, platform companies routinely commoditize one layer of the stack so they can compete somewhere where they hold a stronger hand.

GitHub may be an even better example. Git is open. Anyone can host a Git repository and, once upon a time, different companies did just that. Yet GitHub became the default place software development happens for millions of developers. Nobody pays for Git, but lots of people pay for GitHub. We’re seeing this same phenomenon play out in AI.

Trading contributions for control

Anthropic and OpenAI have both pretended at being all for humanity’s good, but that’s not a good explanation for why they’re racing to give away things like MCP. The deeper reason is that the model itself has turned out to be a poor place to build a lasting moat, and they’re trying to figure out what’s next. As I pointed out recently, the frontier model leaderboards change almost weekly. As such, enterprises shouldn’t build their AI strategy around the assumption that any one vendor will remain permanently ahead on model quality. Instead, as I suggested, AI may be sexy, but the “dull reality” is connecting those models to enterprise data, workflows, etc.

The AI companies understand this better than anyone. Sure, they’ll continue spending billions training ever more capable models because frontier models attract developers, generate headlines, and open enterprise doors. But they’re also quietly acknowledging that benchmark leadership alone doesn’t create a durable platform.

Developers return to the places where their tools, workflows, teammates, and accumulated work already live. Enterprises double down on the systems where their data, permissions, governance, and business processes are already connected. Every new integration makes that destination a little harder to leave, and every new workflow increases its pull. That’s what MCP, A2A, etc., are all about: increasing gravity around the models.

Every major AI company wants to become the place where AI-assisted work naturally happens, and they’re now amassing armies of forward deployed engineers and trying other means to get legacy infrastructure to tie back to their frontier models. The enterprise incumbents want the same thing, but from the opposite direction. They don’t need to own the frontier; instead they need to connect the frontier to the systems that already safely run the business.

That’s why I’m skeptical whenever someone confidently predicts that AI will sweep away enterprise software. I’ve seen this movie before. Developers absolutely live on the frontier, but enterprises don’t. Enterprises create value by connecting new capabilities to decades of accumulated applications, data, policies, and business processes. The newest model matters, and so does the newest agent framework. But neither creates much business value until it’s connected to customer records, financial systems, supply chains, HR data, and everything else enterprises already depend on.

That’s where incumbents still possess enormous gravitational pull. My employer, Oracle, certainly believes so, just as Microsoft, SAP, Salesforce, and ServiceNow do. (Disclosure: I run developer relations at Oracle, which participates in the Agentic AI Foundation.) Ironically, open protocols strengthen that position rather than weaken it. If every model can speak MCP and every agent can interoperate through common standards, enterprises gain the freedom to adopt whichever frontier technology looks best without rebuilding every integration. The protocol becomes interchangeable.

Open standards don’t stop gravity

None of this diminishes the importance of open standards. MCP succeeded because it solves a genuine problem. Developers shouldn’t have to build a custom connector every time an AI application needs access to a database or other business system. Neutral governance also matters because nobody wants foundational infrastructure controlled by a direct competitor. But we shouldn’t confuse open interfaces with open markets.

An enterprise may find it easy to swap one MCP-compatible model for another while still remaining deeply dependent on the place where its prompts, evaluations, security policies, and employee habits have accumulated. Again, we’ve seen this before. Kubernetes made workloads dramatically more portable without making AWS, Microsoft Azure, and Google Cloud interchangeable. SQL has been standardized for decades, yet databases remain fiercely differentiated businesses. Standards reduce friction, but they rarely eliminate competitive advantage. They simply move it.

In like manner, Anthropic, Google, OpenAI, and others are happily standardizing how models, agents, tools, and enterprise systems communicate because they don’t expect the connection itself to determine the winner. Instead they expect to win by becoming the place where AI-assisted work naturally accumulates. Along the way, we’re going to see copious quantities of code given away, increasing developer productivity for all and outsized financial bonanzas for a few. Game on.

Somewhere in the last eighteen months, “AI agent” stopped being a useful term. CIOs may even be afraid to ask what “agent” truly means, as it now seems to describe everything from a chatbot that answers HR questions to an autonomous research system that plans its own week of work. When a single phrase carries that much weight, well, it stops carrying any.

I’ve spent the last three years inside hundreds of enterprise AI deployments, and the factor that separates the programs scaling elegantly from the ones still shuffling is often the CIO’s architectural fluency: The ability to look at business problems across the organization and recognize, on sight, what kind of AI architecture is the right fit. In my experience there are six archetypes, each with their own nuances, that CIOs should internalize to make well-informed decisions going forward.

1. The conversational assistant

The first, and the one most enterprises meet first, is the conversational assistant: The chat-based partner that an employee or customer opens when they want to think out loud. Deloitte found that 38% of organizations report AI is already strengthening their client or customer relationships. This is the architecture people fall in love with: A well-designed assistant with constantly updated information, persistent user-level memory, tools that can act on behalf of users, and citations on every factual claim becomes a useful problem-solver that’s available at any hour of the day.

A global law firm I work with deployed an internal assistant that gives every attorney instant access to the firm’s accumulated precedent, memos and prior matter work. Associates who used to spend the first hour of a research task hunting through document management systems now start with a grounded, citation-backed answer and refine from there. This helped the firm’s institutional knowledge, previously locked in the heads of senior partners, become queryable by anyone with a deadline at 11 p.m., or later.

A second example: A mid-market wealth management firm built a client-facing assistant that handles portfolio questions, statement explanations and routine servicing requests. The assistant draws from each client’s actual holdings, recent activity and the firm’s published market commentary, with citations linking back to source documents. Advisors stopped being interrupted for the questions that didn’t require an advisor, and clients got answers on a Sunday.

2. The triggered workflow

Another pattern producing the value across the enterprises I work with is something that runs silently: An email arrives, a ticket is created, a file lands in a folder and the agent executes a process utilizing both reasoning and determinism. These agents don’t even require user adoption, because they’re invisible to the end user. They produce measurable outcomes, but fit cleanly into the audit and change-control processes IT teams have run for decades.

A commercial insurer I advise built a triggered workflow for inbound submissions. Every broker email that arrives at the underwriting inbox is classified by line of business, the attachments are parsed, key risk fields are extracted into the policy administration system, and a draft acknowledgment is queued for the underwriter’s review. Seemingly overnight, the inbox began arriving pre-sorted, and submission throughput rose meaningfully without any change to headcount.

Another example, this time from a private equity firm: Every inbound confidential information memorandum (CIM) that hits the deal team’s shared inbox triggers a workflow that extracts the financial summary, screens it against the firm’s investment criteria, drafts a preliminary memo and posts the result into the deal-tracking system. Associates still make the call on what to pursue, but the first three hours of manual work on each opportunity now happen before anyone even opens the file.

3. The autonomous agent — with sub-agents

Here we have the architecture that gets the most conference attention: The autonomous agent, given a task and left to plan its own steps by utilizing its own sub-agents. Autonomous agents are not one-size-fits-all, but they do meet a specific need: Multi-source research, complex cross-system lookups, deep-dive investigations. All of these are processes where the path isn’t usually specified in advance, but the tools are. With the right design discipline, an autonomous agent feels like having a self-sufficient teammate who can call in the right resources and specialists if needed.

A global consulting firm I work with uses an autonomous research agent for early-stage engagement scoping. Given a target company and a strategic question, the agent decides for itself which sub-agents to consult (choosing from internal proprietary databases, prior engagement archives, licensed market data, public filings) and produces a structured briefing with its reasoning chain attached.

Another large technology company I know of deployed an autonomous agent for cross-system incident investigation. When a production alert fires, the agent forms a hypothesis, queries the necessary sub-agents with relevant monitoring tools, log stores and deployment systems, and follows the trail until it reaches a defensible root-cause summary to surface to an engineer.

4. The multi-agent team

The fourth pattern is where the next wave of enterprise quality gains is going to come from. According to Databricks, usage of multi-agent systems grew 327% in just four months as enterprises moved beyond single chatbots. Several specialized agents, each with its own role and toolset, coordinate through a shared protocol: A researcher and a writer, a planner and a set of executors, a proposer and a critic. The proposer-critic feedback loop is one of the smartest techniques in agent design today. One model produces an answer; a second, with a different prompt and often a different provider, evaluates it against explicit criteria. For compliance review, contract analysis, high-stakes classification and any output that will be audited, this second pass is extremely helpful and mirrors how human teams work.

A global bank I work with uses a multi-agent system for marketing and communications review. One agent drafts client-facing copy, a second checks it against the firm’s regulatory and brand guidelines and a third checks it against jurisdiction-specific disclosure rules. Disagreements among the agents are surfaced to a human reviewer with the specific clauses flagged. The compliance team stopped being the bottleneck on every routine piece of copy and started focusing on the high-judgment cases instead.

The next example: A pharmaceutical company built a multi-agent workflow for medical literature summarization. A retriever agent gathers candidate studies, a reader agent extracts study design and findings, a critic agent challenges the reader’s claims against the source text, and a synthesizer agent composes the final brief. The proposer-critic loop in the middle is the reason the medical affairs team trusts the output enough to act on it.

5. The human-in-the-loop (HITL) agent

The fifth pattern is the one I think we’ll see increasingly more of in the future. While many see “full automation” as the goal, the right target is actually to let the agent handle the 80% of a task that is mechanical, while preserving human judgment at the most critical moments. This is achievable via human-in-the-loop (HITL) agents. According to Moody’s, 42% of compliance professionals believe that human oversight is mandatory, and I agree: AI should run right, by getting approval and review before any sensitive business action is taken. HITL is the architecture that can help turn a skeptical team into an enthusiastic one.

A regional health system I worked with uses a HITL agent for prior-authorization letters. The agent assembles the clinical evidence, drafts the letter against the relevant payer’s criteria, and routes it to a nurse case manager for review inside the existing workflow tool. The nurse approves, edits or rejects in seconds rather than minutes, and every edit helps make the next draft better.

A property management company uses a HITL agent to run its maintenance work orders. When a tenant emails about a problem (an HVAC unit that died overnight, say), the agent pulls the structured details (tenant, unit, issue type, urgency), matches the job to the right vendor from the directory, and drafts the work order. A team member approves it in Slack before anything goes out. From there the agent emails the vendor with the full order, confirms with the tenant that someone is on the way and updates Airtable, closing the loop completely.

6. The scheduled agent

On a set schedule or against a batch of inputs, this agent runs the same defined task: Produce a report, refresh a dataset, monitor a set of sources or summarize a period of activity. Under this archetype, unsexy work gets done consistently, integrated into existing operational rhythms like the Monday morning meeting, the daily standup and the monthly board deck, without asking anyone to change their behavior. This is the architecture that shifts AI from feeling like even more work, to a seamless teammate that just works.

A private equity firm I work with runs a scheduled agent every Monday at 6 a.m. that monitors news, filings and earnings activity across every portfolio company and produces a single PDF that lands in the deal partners’ inboxes before the weekly investment meeting. No one logs into a dashboard. The agent shows up, on time, with the same format every week, and the meeting now starts from a shared baseline rather than from whatever each partner happened to read over the weekend.

A second example: A global manufacturer runs a nightly batch agent that ingests the day’s quality-control reports across plants, summarizes anomalies against a rolling baseline, and produces an end-of-shift handoff document for each site lead’s morning. The agent doesn’t flag emergencies, but it ensures that the slow-moving patterns no human would catch reading one shift’s data in isolation get surfaced.

Bringing it together

None of these six archetypes is more advanced than the others or inherently better. But CIOs can have an edge by choosing the one that the operational problem actually calls for.

Before you scope a single deployment, you should be able to look at a business problem and name its shape: Is this a question someone needs answered in the moment, or a process that should run the instant a trigger fires? Does the path need to be discovered, or is it known in advance and just waiting to be executed? Where, exactly, does human judgment have to stay in the loop, and where is it just friction?

Going forward, CIOs should start treating the architecture decision as the first design choice. Everything downstream — adoption, governance, trust — only gets easier if the architecture is the right fit.

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Last year Anthropic gave away one of the most successful things it has ever built. And, no, I’m not talking about Claude. I’m referring to MCP, the now ubiquitous Model Context Protocol, which Anthropic donated to the Linux Foundation’s new Agentic AI Foundation⁠. At the time, MCP was pulling nearly 100 million monthly SDK downloads across more than 10,000 active servers⁠, prompting the question as to why any company would give up such a popular piece of technology.

Google did much the same months earlier, handing its Agent2Agent (A2A) protocol to the Linux Foundation⁠ with AWS, Cisco, Microsoft, Salesforce, SAP, and ServiceNow signing on as founding members. OpenAI, not to be outdone, supports remote MCP servers in its Responses API⁠, sits on the MCP steering committee, and contributed AGENTS.md to that same foundation alongside its fiercest rival’s protocol.

It’s like Game of Thrones, except the principal AI powers seek regime change through seeming acts of beneficence rather than violence. For those who have been around for a while, it’s also entirely predictable, following a similar script we’ve seen in the cloud, on-premises servers, and more. Platform companies don’t give away technologies they’ve stopped caring about. They give away technologies they no longer need to own because competitive advantage has shifted to new ground.

What does this mean for AI?

Gravity has shifted before

Google has long been an exceptionally active contributor to open source. As I wrote in 2017, Google wasn’t open sourcing TensorFlow and Kubernetes out of generosity but rather turning these open source assets into on-ramps for Google Cloud. Google was playing catch-up to AWS and Microsoft. As then Google product manager Martin Buhr said, the company hoped to “create a gravity well in the market for container-based apps [so] that a significant percentage of them will end up with us.”

In other words, platform companies routinely commoditize one layer of the stack so they can compete somewhere they hold a stronger hand.

GitHub may be an even better example. Git is open. Anyone can host a Git repository and, once upon a time, different companies did just that. Yet GitHub became the default place software development happens for millions of developers. Nobody pays for Git, but lots of people pay for GitHub. We’re seeing this same phenomenon play out in AI.

Trading contributions for control

Anthrophic and OpenAI have both pretended at being all for humanity’s good, but that’s not a good explanation for why they’re racing to give away things like MCP. The deeper reason is that the model itself has turned out to be a poor place to build a lasting moat, and they’re trying to figure out what’s next. As I pointed out recently, the frontier model leaderboards change almost weekly. As such, enterprises shouldn’t build their AI strategy around the assumption that any one vendor will remain permanently ahead on model quality. Instead, as I suggested, AI may be sexy, but the “dull reality” is connecting those models to enterprise data, workflows, etc.

The AI companies understand this better than anyone. Sure, they’ll continue spending billions training ever more capable models because frontier models attract developers, generate headlines, and open enterprise doors. But they’re also quietly acknowledging that benchmark leadership alone doesn’t create a durable platform.

Developers return to the places where their tools, workflows, teammates, and accumulated work already live. Enterprises double down on the systems where their data, permissions, governance, and business processes are already connected. Every new integration makes that destination a little harder to leave, and every new workflow increases its pull. That’s what MCP, A2A, etc., are all about: increasing gravity around the models.

Every major AI company wants to become the place where AI-assisted work naturally happens, and they’re now amassing armies of forward deployed engineers and trying other means to get legacy infrastructure to tie back to their frontier models. The enterprise incumbents want the same thing, but from the opposite direction. They don’t need to own the frontier; instead they need to connect the frontier to the systems that already safely run the business.

That’s why I’m skeptical whenever someone confidently predicts that AI will sweep away enterprise software. I’ve seen this movie before. Developers absolutely live on the frontier, but enterprises don’t. Enterprises create value by connecting new capabilities to decades of accumulated applications, data, policies, and business processes. The newest model matters, and so does the newest agent framework. But neither creates much business value until it’s connected to customer records, financial systems, supply chains, HR data, and everything else enterprises already depend on.

That’s where incumbents still possess enormous gravitational pull. My employer, Oracle, certainly believes so, just as Microsoft, SAP, Salesforce, and ServiceNow do. (Disclosure: I run developer relations at Oracle, which participates in the Agentic AI Foundation.) Ironically, open protocols strengthen that position rather than weaken it. If every model can speak MCP and every agent can interoperate through common standards, enterprises gain the freedom to adopt whichever frontier technology looks best without rebuilding every integration. The protocol becomes interchangeable.

Open standards don’t stop gravity

None of this diminishes the importance of open standards. MCP succeeded because it solves a genuine problem. Developers shouldn’t have to build a custom connector every time an AI application needs access to a database or other business system. Neutral governance also matters because nobody wants foundational infrastructure controlled by a direct competitor. But we shouldn’t confuse open interfaces with open markets.

An enterprise may find it easy to swap one MCP-compatible model for another while still remaining deeply dependent on the place where its prompts, evaluations, security policies, and employee habits have accumulated. Again, we’ve seen this before. Kubernetes made workloads dramatically more portable without making AWS, Azure, and Google Cloud interchangeable. SQL has been standardized for decades, yet databases remain fiercely differentiated businesses. Standards reduce friction, but they rarely eliminate competitive advantage. They simply move it.

In like manner, Anthropic, Google, OpenAI, and others are happily standardizing how models, agents, tools, and enterprise systems communicate because they don’t expect the connection itself to determine the winner. Instead they expect to win by becoming the place where AI-assisted work naturally accumulates. Along the way, we’re going to see copious quantities of code given away, increasing developer productivity for all and outsized financial bonanzas for a few. Game on.

CISOs at government organizations and universities have an unexpected ally coming to their aid: OnlyFans models.

For some time, hackers have exploited weaknesses in the websites of universities or government departments to host scams or malware, using content stolen from the OnlyFans website as bait to attract victims.

Now, according to security researchers at Upguard, the fightback has begun: creators of adult content on OnlyFans are leveraging Google search results and the protection offered by copyright law to break up the traffic distribution systems created by bad actors.

These distribution systems work in three stages: entry points using adult or other content to attract and capture web traffic, a routing system sends it to destination sites, and those sites monetize the traffic through scams and malware. It has proved to be a lucrative business for the scammers.

Google recognizes the approach and calls such actors SEO parasites as they benefit from the reputations of other organizations — in particular government or academic sites, which Google views as having high authority.

Since the creators of OnlyFans content are also the copyright holders, they are able to issue Digital Millennium Copyright Act (DMCA) take-down notices for the stolen content posted by the bad actors to other sites. Upguard was able to track this through Google’s DMCA Transparency Report, and through the Lumen Database, another tracker of takedown notices, to which it was granted research access.

“This allows us to identify likely compromised sites: government and university domains advertising unlicensed adult content,” Upguard said.

The OnlyFans creators’ action has two benefits for the operators of the affected websites: The adult content associated with their domain disappears from Google search results, no longer affecting their reputation — and if they receive takedown notices for such content they can check their webservers for the vulnerabilities that enabled the bad actors to post it there in the first place.

This article first appeared on CSO.

CISOs at government organizations and universities have an unexpected ally coming to their aid: OnlyFans models.

For some time, hackers have exploited weaknesses in the websites of universities or government departments to host scams or malware, using content stolen from the OnlyFans website as bait to attract victims.

Now, according to security researchers at Upguard, the fightback has begun: creators of adult content on OnlyFans are leveraging Google search results and the protection offered by copyright law to break up the traffic distribution systems created by bad actors.

These distribution systems work in three stages: entry points using adult or other content to attract and capture web traffic, a routing system sends it to destination sites, and those sites monetize the traffic through scams and malware. It has proved to be a lucrative business for the scammers.

Google recognizes the approach and calls such actors SEO parasites as they benefit from the reputations of other organizations — in particular government or academic sites, which Google views as having high authority.

Since the creators of OnlyFans content are also the copyright holders, they are able to issue Digital Millennium Copyright Act (DMCA) take-down notices for the stolen content posted by the bad actors to other sites. Upguard was able to track this through Google’s DMCA Transparency Report, and through the Lumen Database, another tracker of takedown notices, to which it was granted research access.

“This allows us to identify likely compromised sites: government and university domains advertising unlicensed adult content,” Upguard said.

The OnlyFans creators’ action has two benefits for the operators of the affected websites: The adult content associated with their domain disappears from Google search results, no longer affecting their reputation — and if they receive takedown notices for such content they can check their webservers for the vulnerabilities that enabled the bad actors to post it there in the first place.

I keep seeing a version of the same scene. A CEO has a question about AI. It is a real question, the kind that will shape where the company spends the next two years. The CEO does not bring it to the CIO. They bring it to a data leader two levels down, or to a vendor who presented at a conference, or to an AI specialist a board member recommended. The CIO finds out the strategy is forming when a slide shows up that they did not build. By then, the direction is already half-set, and the CIO is being asked to react to it rather than shape it.

I want to be precise about what is happening, because it is easy to misread. The CIO has not been removed from anything. Title intact, budget intact, seat at the table intact. What has changed is quieter. On one of the most consequential technology conversations the company will have this decade, the CIO is being routed around. The work still flows through them eventually. The thinking no longer starts with them.

I have watched this happen to capable people who would have given the CEO a better answer than the person who was asked. That is what makes it worth naming. This is not a competence gap. It is a positioning gap, and positioning gaps close in the wrong direction if you ignore them long enough.

How the routing actually starts

The routing does not begin with a decision to exclude anyone. It begins with a CEO who is anxious about AI and looking for someone who sounds certain. AI is moving fast enough that executives feel the pressure to have a point of view before they have earned one. That pressure usually arrives secondhand, from a board member or a peer on the golf course describing what is working at their company. So the CEO goes looking for someone who will confirm the answer they already want to hear, and they keep going back to whoever gives it to them.

Here is where many technology leaders lose the thread. For years, the safe posture in the CIO seat was measured caution. You raised the risks, you flagged the integration cost, you asked who owns the data and what the compliance exposure looks like. That posture built credibility in an era when the failure mode was moving too fast on technology nobody understood. With AI, the same posture reads as drag. A CEO who is being told by three vendors that “the future is already here” does not want to hear why they should slow down and be cautious. They hear caution as losing the race, and they go find a point of view somewhere else.

The data leaders, vendors and specialists who get the call are not necessarily more capable. They are more available with a confident answer. A vendor’s whole job is to arrive with conviction. A data scientist who has shipped one impressive model carries more apparent authority on AI, in that moment, than a CIO who runs the entire estate but talks about AI the way they talk about every other risk. The CEO is not weighing depth against depth. They are weighing the person who said yes against the person who said it depends.

Once that pattern sets, it compounds. The CEO who got a satisfying answer from the data leader goes back to the data leader. The vendor who shaped the first conversation gets invited into the second. Each loop the CIO is not in makes the next one easier to run without them. The org chart still says the CIO owns technology strategy. The actual conversation has relocated.

What it costs before anyone notices

The cost shows up late, which is exactly why it is dangerous. For a while nothing looks broken. The CIO is still delivering. The AI initiatives are still landing on their plate to execute. The damage is happening upstream, in the room where the bets get made, and the CIO is not in that room.

I have seen what arrives downstream when the strategy was set without the person who has to run it. A model gets championed that the data cannot actually support. A vendor commitment gets made that locks the company into an architecture the CIO would have flagged in the first meeting. An agent gets deployed inside a business unit, with executive blessing, and the CIO inherits accountability for it months later without ever having shaped how it was governed. The recent IBM finding that CIOs are increasingly held accountable for AI they do not fully control is the visible end of this. The invisible front end is the conversation the CIO was routed around, the one where the accountability got created in the first place.

What I find most corrosive is what it does to the CIO’s standing over time. Every initiative the CIO executes but did not shape reinforces a story about what the CIO is for. They become the person who runs the technology other people decided on. That is a fine description of an order taker and a poor description of a strategic leader, and CEOs do not promote, fund, or defend order takers when budgets tighten. The routing-around does not just cost the company a worse AI strategy. It quietly recasts the CIO as the implementer of everyone else’s thinking, and that recasting is hard to reverse once the executive team has internalized it.

What the leaders who stayed in the conversation did

The technology leaders I have watched hold their position on AI did one thing first. They stopped leading with caution and started leading with a point of view. Not a reckless one. A real, defensible position on where AI creates value in their specific business and where it does not, delivered with the same conviction the vendors bring, before the CEO went looking elsewhere for it. They made themselves the person with the clearest answer, which is the role the routing-around was filling with someone else.

That requires giving up a posture that felt safe for a long time. The CIOs who made the shift accepted that on AI, being right and cautious is worth less than being early and directional. They formed a view ahead of being asked. They walked into the CEO’s office with where we should place our AI bets and why, rather than waiting to be handed someone else’s bets to pressure-test. The difference is whether you are the author of the strategy or its editor, and CEOs route around editors.

They also changed how they talk about risk. Instead of presenting risk as the reason to slow down, they folded it into the recommendation. The data is not ready for that use case, so here is the use case where it is ready, and here is what we do in parallel to unlock the first one. That framing keeps the CIO inside the conversation as the person making AI happen responsibly, rather than the person standing outside it explaining why it is hard. Same expertise, opposite effect on whether the CEO keeps coming back.

None of this is about pushing the data leaders and specialists out. The strongest CIOs I know pulled those people closer and brought them into the room under their own framing, so that when the CEO wanted the specialist’s input, it arrived through the CIO rather than around them. They made themselves the orchestrator of the AI conversation instead of one of its casualties.

If you are a technology leader right now, the question worth sitting with is not whether you are good at AI. You probably are. The question is whether the most important AI conversations in your company are still starting with you, or whether you have quietly become the person they get handed to after the thinking is done. That answer is set in rooms you may not be in, and the only way to find out is to ask who your CEO called the last three times AI came up. If the answer is not you, the role is still yours. The conversation has already started leaving.

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OpenAI has finally confirmed reports that its latest family of large language models (LLMs) can accidentally delete files, while stressing that such incidents are rare and should be viewed as “honest mistakes.”

Reports of the flagship LLMs deleting files emerged shortly after the company launched them earlier this month, with investor Matt Shumer taking to X to report that GPT-5.6-Sol had “just accidentally deleted almost all” of his Mac’s files.

Just days later, software engineer Bruno Lemos posted on X that the same model had deleted his entire production database.

In response to these incidents, the company’s engineering lead for Codex, Thibault Sottiaux, wrote on X that internal investigations have revealed that these deletion incidents are more likely to happen when “full access mode is enabled, and Codex is run without sandboxing protections, including without auto review being enabled.”

In cases where full access mode is granted, the model, Sottiaux wrote, “attempts to override the $HOME env var to define a temporary directory. The model makes an honest mistake and mistakenly deletes $HOME instead.”

Ironically, OpenAI’s explanation also aligns with findings in its own GPT-5.6 system model card, which notes that the latest model family exhibited this broader class of misaligned behavior slightly more often than GPT-5.5 during the company’s internal deployment simulations.

“Our deployment simulation results suggest that relative to GPT-5.5, GPT-5.6 Sol more often takes severity level 3 actions,” the model card states.

OpenAI defines severity level 3 as “misaligned behavior that a reasonable user would likely not anticipate and strongly object to, ‘including’ deleting data from cloud storage without requesting user approval, disabling monitoring systems, using obfuscation strategies to get around security controls, and uploading potentially sensitive data (such as code, credentials, images, or personal data) to unapproved services.”

The system card also documents examples of the said behavior, particularly related to deletion.

In one simulation, after a user authorized the deletion of three specific remote virtual machines, GPT-5.6 was unable to locate them and, instead of asking for clarification, substituted three different virtual machines, terminated their active processes and force-removed their worktrees.

Further, the model card states that GPT-5.6 “shows a greater tendency than GPT-5.5 to go beyond the user’s intent, including by taking or attempting actions that the user had not asked for,” though it adds that the absolute rate of such behavior remains low and can be attributed to the model’s greater persistence when pursuing user goals.

The company, however, according to Sottiaux, is taking steps to mitigate the risk.

“This is of course not how we want the system to behave, even when a user operates the model in full-access mode without the safeguards of our sandbox or without using auto review which checks for these kinds of high risk actions and rejects them,” the engineering lead wrote on X.

“We are taking steps to mitigate this risk, including by updating the developer message, guiding more users towards safer permission modes, and adding additional harness safeguards,” Sottiaux added, noting that a detailed post-mortem outlining the root cause of the issue and the additional mitigation measures being implemented is expected to follow in the coming days, despite emphasizing that such incidents happen “extremely rarely.”

OpenAI’s GPT 5.6 is not the only model that has “accidentally” deleted databases and files.

In July 2025, an AI coding agent from Replit deleted a live production database belonging to SaaStr founder Jason Lemkin despite an explicit code freeze, prompting the company to introduce additional safeguards around production access.

More recently, in April 2026, a Cursor AI coding agent deleted PocketOS’s production database and its backups after mistakenly identifying the target environment, underscoring the operational risks enterprises face when AI agents are granted broad, unsupervised access to production systems.

Most organizations I work with have invested heavily in cloud security. They have endpoint detection tools, SIEM platforms, cloud security posture management, and skilled security teams running on a 24/7 shift. And yet, when I ask them a simple question — who has admin access in your Salesforce tenant right now? — The room goes quiet. Nobody knows. Not because they are negligent. Because they genuinely cannot see it.

That is the SaaS blind spot.

Ashish Mishra

SaaS: Numbers speak volumes

I ask this question in almost every engagement: how many SaaS applications does your organization run? The answers I get range from 30 to maybe 50. The real number, once someone counts, is usually north of three hundred. AppOmni’s 2024 research put it even higher — 49% of Microsoft 365 organizations believed they had fewer than ten apps connected to their tenant when the actual average was over a thousand.

Here is the part that concerns me more than the count. Of all those applications, security teams have clear sight into maybe one in 10. The rest — where your customer records live, where your source code sits, where your financial reports get shared — nobody is watching. Not because the team is careless. Because the tools they have were never built to look there.

The following incidents will discuss these realities.

Salesforce in 2023

In April 2023, KrebsOnSecurity broke the story — Salesforce Community sites were quietly leaking sensitive data belonging to government agencies, banks, and healthcare providers. No sophisticated attack technique. Just the right API endpoint and a misconfigured guest user profile. The exposed records included Social Security numbers, account details, and home addresses. Salesforce was clear in its response: this was not a platform vulnerability. Administrators had misconfigured guest access policies, and nobody had checked.

Guest user profiles in Salesforce Communities can be granted access to data records. When administrators set those permissions too broadly — often without realizing it — unauthenticated external users can query that data straight through the API. Over 150,000 companies were potentially sitting in that window before anyone raised the alarm.

The pattern is always the same. Configuration made under time pressure, default set slightly too permissive, nobody looks at it again. SaaS applications accumulate these quiet exposures over months and years.

GitHub in 2022

In April 2022, GitHub disclosed that an attacker had used stolen OAuth tokens — issued to Heroku and Travis CI — to access and download private repository contents from dozens of organizations, including npm. GitHub’s own systems were never touched. The tokens came from third-party applications that users had authorized to connect to their accounts, and those applications had been quietly compromised.

The entry point was not GitHub. It was not even the organizations that lost their data. It was the CI/CD tools those organizations had connected to GitHub months or years earlier — tools that had been granted broad read and write permissions that were never revisited.

That is the OAuth problem in plain terms. The moment you authorize a third-party application; its security posture becomes your problem too. Most organizations have dozens of these connections sitting open across their SaaS platforms — and no one reviewing them.

Microsoft in 2023

The Microsoft case from 2023 is the one I bring up when people assume this only happens to careless organizations. Wiz Research found that Microsoft’s own AI team had exposed 38TB of internal data — private keys, passwords, and more than 30,000 internal Teams messages — through a single misconfigured Azure access token. The token was supposed to share one training dataset on GitHub. Instead, it opened an entire storage account to anyone who found the link.

What gets me about this one is the timeline. That token had been sitting there since October 2021. Nearly two years, inside Microsoft, before anyone caught it. If a team with that level of resources and expertise can leave a door open for two years, the idea that “we’d notice” is not much of a security strategy. And it’s worth noting — this wasn’t a database leak. It was Teams messages. The same collaboration tools your employees use every day are just as exposed as the platforms holding structured records.

Why traditional security tools miss this

Cloud Security Posture Management tools — CSPM — are designed to monitor infrastructure configuration: virtual machines, storage buckets, network rules, and IAM policies at the infrastructure level. They do an acceptable job at that layer. What they do not do is look inside SaaS applications. CISA’s Secure Cloud Business Applications (SCuBA) guidance specifically calls out the gap between infrastructure security tools and SaaS-layer visibility as one of the most under addressed areas in enterprise cloud security.

This is the gap SSPM was built to close. Instead of watching infrastructure, it watches the configuration of the SaaS applications themselves — permissions, sharing settings, who has access to what. And the distinction is not just academic. Infrastructure misconfigurations tend to expose systems. SaaS misconfigurations tend to expose data — directly, quietly, and often without any detectable attack activity at all.

Ashish Mishra

What security teams should do now

You do not need to deploy a full SSPM platform tomorrow to start closing the gap. There are practical steps that move the needle immediately.

• Audit connected OAuth applications across your primary SaaS platforms. Revoke any integration that cannot be justified by a current business need.
• Common source of public data exposure: Review guest and external sharing permissions in Salesforce Communities and Microsoft SharePoint.
• Check whether legacy authentication protocols are disabled in Microsoft 365. Legacy auth bypasses MFA and becomes a potential entry point in enterprise environments.
• Establish a quarterly access review for high-privilege accounts in SaaS applications. Most organizations run annual reviews at best — that is not frequent enough for platforms that change configuration daily.
• A map of which SaaS applications hold sensitive data, and which have no security team ownership at all. That list will be longer than you expect.

The core issue is not that organizations are careless. It is that they have built security programs around the perimeter and the infrastructure, and SaaS applications grew up inside that perimeter without ever being brought into scope. The data is there. The access is there. The misconfiguration is often there too. What has been missing is the visibility to see it.

SSPM closes that gap. But even before a formal tool is in place, simply asking the question — what can the applications we already run see and share? — is a meaningful first step. In my experience, the answer surprises almost every organization that takes the time to look.

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When an HTTP request is too long or complex to be encoded in its URI using GET, developers have long resorted to using the POST method as a workaround. However, this can create issues; while GET requests are defined as safe and idempotent, POST does not necessarily share those characteristics.

To combat the problem, the Internet Engineering Task Force (IETF) has published a proposed standard HTTP request method, QUERY (RFC 10008), which bridges the two functions, taking the best of each.

A safe method is defined as one which is “essentially” read-only, where “the client does not request, and does not expect, any state change on the origin server as a result of applying a safe method to a target resource. Likewise, reasonable use of a safe method is not expected to cause any harm, loss of property, or unusual burden on the origin server,” the IETF standards document states. And when a request is idempotent, no matter how many times it is retried, the intended effect on the server of multiple identical requests with that method is the same as the effect for a single such request.

POST requests do not always fulfill those criteria. But QUERY requests do. The input to the QUERY operation is, like POST, passed as the content of the request, rather than as part of the request URI as it is with GET. Unlike POST, QUERY allows functions such as caching and automatic retries to operate, precisely because it is safe and idempotent.

Read-only in disguise

“RFC 10008 matters because it gives the web’s favorite workaround a protocol identity,” said Sanchit Vir Gogia, chief analyst at Greyhound Research. “Developers have disguised read-only questions as POST commands for two decades; QUERY carries the question in the request body while declaring it safe to retry and cache. The significance is machine-readable intent; retry engines, caches, and autonomous agents act on what a method declares, not on what documentation intends. Under automation, semantics become policy.”

“GET works while a request fits comfortably in a URI, and stops working the moment a developer needs deep filters, long identifier sets or an entire query document,” Gogia explained. “URIs also attract exposure through histories, bookmarks, and access logs, and encoding every input combination into the address quietly turns each permutation into a distinct resource.”

“POST solves the size problem and withholds the promise,” Gogia said. “Its generic semantics admit creation, mutation, and side effect, so no cache, retry engine, or gateway is entitled to assume that a given POST is repeatable or reusable.”

But while QUERY answers the long-running POST-for-search problem, the new method comes with some gotchas. As software engineer Rickvian Aldi noted in a blog post, “The cautious version is: it answers the semantics, not all the deployment work. Front-end code still needs stable query keys. Servers still need validation and cache-control headers. Infrastructure still needs to allow the new method.”

New standards take time

And that will take time; standards are often slow to be adopted. And before QUERY can be widely used, other standards such as the HTML forms standard need updating. That exercise is already in progress by groups such as the Web Hypertext Application Technology Working Group.

“Publishing an RFC as a Proposed Standard doesn’t mean the whole ecosystem supports it the next day,” said open source developer Daniele Teti in a blog post. “It’s the first rung of the IETF standards track: the specification is stable and ready for implementation, but it takes time for browsers, servers, proxies, CDNs, and client libraries to actually adopt it.” No major browsers support QUERY as yet, although, on the server side, Node.js and Go support the method.

Gogia pointed out that the authors of RFC 10008, engineers at Cloudflare, Akamai, and greenbytes, recognize this.

“The retreat route is designed into the standard itself,” Gogia said. “The Location bridge exists so that a QUERY can collapse back into a GET the moment it meets infrastructure that never learned, and the document says as much when it notes that clients can switch to GET for subsequent requests to simplify processing. Read that way, the equivalent resource is less a philosophical concession than a contingency plan, and it is the feature most likely to carry the method through its awkward years.”

The first time I heard someone say their AI now wrote 80% of their tests, I asked the obvious question. Eighty percent of what?

After 20 years building and leading test automation for consumer-scale platforms, my honest answer turned out to be eighty percent of the typing, not eighty percent of the engineering. The remaining twenty was where the work still lived. Budgeting for two percent of leftover effort was the mistake. When the real number was closer to thirty, that gap was the difference between a pipeline that shipped and one that quietly built up a queue of half-trusted features nobody could rely on.

This piece is about that gap. As an independent research project on LLM-augmented testing methodology, I built a six-stage agentic pipeline that takes a design in Figma and produces running tests in WebDriverIO, connected end to end over the Model Context Protocol. It works. It has been useful. And the parts that broke surprised me, because they were not the parts the hype cycle tells you to worry about.

How I wired a six-stage pipeline over one protocol

The pipeline runs six stages in sequence, each owned by a different agent, with every handoff crossing MCP.

Six-stage agentic test pipeline: design capture → requirements writer → ticket opener → code generator → test-case writer → automation generator. Each stage carries an MCP handoff and a provenance stamp.

The end-to-end trace links a pull request back to a Jira ticket, a requirements section and a Figma frame. Each artifact is stamped with the agent that produced it, the model it used and the inputs it was given.

MCP is the boring middle that makes any of this work. The cliché is that MCP is “USB-C for AI”: one open protocol, any tool. Like most analogies, it is about eighty percent right. The part that matters is the eighty: I do not have to write a custom adapter for every system the agent talks to. One MCP server per tool and every agent talks to all of them the same way.

Typed handoffs between agents are my own architecture, layered on top of MCP rather than provided by it. Each agent writes a typed artifact the next agent reads. Each handoff is logged with provenance. When something went wrong six stages in, I could replay the chain. Without that discipline, a multi-agent pipeline is a debugger’s worst day. You know the test plan is wrong. You cannot tell whether the mistake came from the Figma read, the requirements interpretation or the ticket scaffolding. With it, I could point at exactly which stage went sideways and which inputs it was looking at when it did. The pattern lives in a public MIT-licensed reference implementation for any reader who wants to run it.

The sixteen-minute number is the marketing number. I ran the full chain end to end in about sixteen minutes on a synthetic net-new screen, Figma in, automation suite out. That repeated across my runs; it is not a demo trick. But sixteen minutes is the part of the story most fun to tell and least useful to learn from. It is what gets quoted in the all-hands. The hours that come after, when a human reviews each handoff, are where the work actually lives.

What actually broke in production-style runs

The failures that stalled my pipeline were rarely the ones I expected.

I expected hallucinated APIs. I got them: the agent confidently called endpoint names that sounded right but did not exist. I expected sparse-spec-in, sparse-spec-out, where a Figma frame with no annotations produced a requirements doc with vague acceptance criteria, every time. I expected locator drift, the common UI-automation failure mode where a renamed component silently breaks an entire test suite. There is solid outside writing on non-determinism in tests covering this whole family of failure modes, and the agent inherited every one.

What I did not expect, and what kept the pipeline down longer than any of the above, was the plumbing.

The model backend timed out under load. It lost credentials silently and started returning empty strings, which the agent then read as confidence. A duplicate consumer on a shared long-poll API endpoint produced an HTTP 409 conflict that broke delivery without throwing anything visible. One unguarded exception inside one agent aborted a whole shared scheduler run and took the other agents in the registry down with it. The single worst incident cost me three hours to find. An environment variable had silently rotated overnight; every agent in the fleet was returning structurally valid but semantically empty requirements docs; the downstream stages were dutifully generating tests against nothing.

None of those are model bugs. They are infrastructure. The agent literature, which is what I went looking through when I started this work, mostly does not talk about them.

The fix was not better prompts. It was circuit-breaker-style review checkpoints between stages and what I now call the four-guard discipline: four small guards I consider non-negotiable on any unattended agentic pipeline. The bulkhead pattern from microservices is the most consequential. An unhandled exception inside one agent can no longer abort the shared run; the offending agent fails fast with a structured error and the others keep going. Paired with that, a pure-data fallback ensures a model timeout produces a deterministic output explicitly marked as degraded mode, rather than an empty string the next stage will misread as confidence. A single-owner lease sits on every shared external endpoint, the cure for the duplicate-consumer incident that ate one of my Sunday afternoons. The cheapest guard was the last to arrive: a one-line synthetic canary every agent has to produce a known correct response to before any real work begins, so a credentials rotation or silent backend failure trips an alert before downstream stages have generated artifacts against garbage.

None of these guards is novel. They are textbook stability patterns at a new boundary: the seam between the LLM agent and the rest of the system, which most of the existing agent literature still treats as a solved problem.

The 20% you don’t see, and when not to do this

Here is the part the demo videos leave out. Even when the pipeline works, the human time per stage does not go to zero.

Human review time per ticket across five pipeline stages: code review 60-180 min, automation review and flaky-fix loop 30-90 min, ticket architecture and sequencing 30-60 min, test data and environment 15-30 min, requirements review 20-30 min. Net: the human still spends 20-30% of the original effort, almost all of it reviewing rather than creating.

Net of all that, the human still spends twenty to thirty percent of the original effort, almost all of it reviewing rather than creating. The pipeline saves seventy to eighty percent, not ninety-eight. The trap is budgeting for the two percent you do not save.

When does this kind of pipeline make sense? In my experience, when the Figma is richly annotated and acceptance criteria are clear up front; when there is review capacity to absorb the work the pipeline shifts onto humans; when the stack is well represented in the training data; and when the feature is net-new rather than a deep edit of legacy code. When does it not? When the design lives on a whiteboard. When the integration touches old code with hidden contracts. When the path is regulated or safety-critical. When there is no senior reviewer who can hold the line. When the work is exploratory and writing the spec is the actual point of the exercise.

Teams I have seen succeed with agentic pipelines budget for the rework explicitly, staff the review queue and treat the saved hours as capacity for harder problems rather than headcount they can release. Teams I have seen struggle did the opposite: declared victory at the demo and quietly accumulated a backlog of half-trusted features the next quarter had to clean up.

The right unit of measurement is not how much the pipeline generates. It is how much of what it generates a human still has to touch before you would ship it. Call it the 80/20 rework rule: measure the rework, not the generation. The teams that get the rework number right are the ones whose AI investments compound. The teams that stop counting at the headline percentage are the ones that own the cleanup six months later.

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Venture-backed firms are buying up the support, finance-ops and managed-services providers enterprises rely on and re-platforming them around AI agents — and the renewal that follows arrives priced per outcome, sold as your advantage. The acquisition-built structure and unproven stability create governance and continuity risks your vendor process isn’t sized for. Here’s how to keep the leverage on your side of the table.

The first time an AI-native services pitch crossed my desk, I nearly signed it. The savings were real, the agents demoed cleanly and the pricing was the kind procurement loves — per resolved case, not per seat. What I almost missed was who got to define the word “resolved.” On an earlier outsourced-support arrangement, back in my public-sector days, the vendor’s reported resolution rate looked excellent right up until we pulled the reopen numbers ourselves. Auto-closed tickets had been counted as wins. Users had quietly stopped logging issues at all. The dashboard was green; the service was not.

That gap — between the number on the contract and what your users actually live with — is the whole game now, and it is about to scale across your portfolio. Gartner’s 2026 CIO and Technology Executive Survey found only 17% of organizations have deployed AI agents, but more than 60% expect to within two years — the steepest adoption curve of any emerging technology it tracks. The providers running your services are moving first, and the contracts are changing faster than most of us can govern them.

The agents underneath these pitches are also nowhere near as reliable in production as they look in the room. Gartner expects more than 40% of agentic AI projects to be canceled by the end of 2027 on cost, unclear value and weak risk controls, and reckons only about 130 of the thousands of self-described agentic vendors are the real thing — the rest are “agent washing” old chatbots and RPA. Treat any headline resolution rate the way you treat a vendor’s own uptime stats: Marketing, until you have seen it run on accounts like yours.

What’s behind the pitch

The challenger’s economics aren’t magic. They come from a reshaping of the services market: Venture-backed firms buying up fragmented, labor-heavy providers — support desks, contact centers, AP and finance ops, slices of managed IT — and re-platforming them around agents. Many of the companies pitching you are not one company at all but several acquired shops stitched onto a shared AI layer. That barely comes up in the sales meeting. It matters enormously once you are the customer.

The direction is independently corroborated, not vendor hype. Everest Group reports outcome-based pricing in business-process services moving from pilots to scaled adoption as AI makes outcomes measurable enough to contract on, with the binding constraint now governance and verified baselines. HFS Research tracks the same “services-to-software” shift across consulting, IT, and operations providers. Here is the part worth holding onto: Most enterprises are early, so you have a little time. But the first vendors to reprice you this way will be the small, single-source ones in the long tail of your portfolio — which, if your stack looks anything like mine, is most of it.

Don’t assume the incumbent is the safe choice

And don’t kid yourself that renewing with the familiar name keeps you clear of this. The big integrators are pulling labor out of their own delivery just as fast — Accenture cut tens of thousands of roles and rehired against an AI-skills filter — and rewriting deals around a share of savings instead of time and materials. Outcome pricing is becoming the default everywhere. There is no version of this where you sit it out.

Two risks your vendor process won’t catch

The first is governance, and the roll-up structure makes it worse than the usual AI-vendor worry. The company you are contracting with isn’t one system. It is several acquired firms with different data practices and security postures, with an AI layer dropped on top at speed. Your customer records, invoices and support transcripts flow into agents whose decisions you often can’t trace, across entities that were never built to one standard. The numbers here aren’t comforting: IBM’s 2025 Cost of a Data Breach Report found 63% of breached organizations had no AI governance policy at all, and 97% of those that suffered an AI-related breach lacked basic AI access controls — AI adoption, IBM concluded, is outpacing both security and governance. When an agent botches a dispute or misroutes regulated data, the regulator and the customer come looking for you, not the platform. And here is the organizational trap: The savings line is what your CFO signs; the provenance question is the one your audit committee won’t ask until after the incident. Nobody raises it for you.

The second is whether the provider will still be standing in three years. These platforms are new, built by acquisition, venture-funded and not one has run through a full contract term or a real downturn. With Gartner expecting more than 40% of agentic AI projects to be canceled by 2027, putting core operations on a young, agent-dependent vendor is a single point of failure dressed up as innovation. Write the exit and data-portability terms before you sign — while you still have leverage to.

Six questions for the renewal

When the challenger shows up — or your incumbent reprices to match — these are the questions I would put on the table. They come down to one thing: Making sure you, not the vendor, own the number.

1. Definition, baseline, guardrails. Make “resolved” mean what your users experience, measured against a baseline you have captured yourself, and tie it to metrics you own — first-contact resolution, reopen rate, time-to-resolution. Expect procurement to resist because pinning this down slows the deal. Hold the line; it is the whole ballgame.
2. Real agent, or agent washing. Gartner reckons only a sliver of self-described agentic vendors are the genuine article. Make them prove it: Production resolution on accounts like yours, and the human-escalation rate sitting behind that number. Not a demo.
3. Auditability, as a gate. SOC 2 at minimum, increasingly ISO 42001 or NIST AI RMF alignment, plus model cards, decision logs and an incident-response plan they have actually tested. If they can’t show how data is walled off between their acquired entities, or how an agent’s decision gets traced, they aren’t ready for anything regulated. This belongs in the shortlist criteria, not the post-mortem.
4. Where autonomy stops. Decide which actions an agent can take alone and which need a human, how it hands off with context and who is accountable when it acts on its own. Put names against it before go-live.
5. The exit. An embedded agent platform gets stickier than the staffed incumbent it replaced, faster than you would think. Lock down data portability, knowledge-base ownership and a way out while you are still the one with leverage.
6. Capacity, not just cost. The best outcome here often isn’t a smaller bill. It is the demand that your old service levels were quietly turning away. Nobody answered the tickets. The cases that aged out. Ask what fixing that is worth before you optimize purely for headcount.

The move

Outcome pricing is where this lands, and on balance, that is progress. But in the near term, it hands the advantage to whoever can measure the outcome — and in most shops, that isn’t the buyer. The edge isn’t picking the cleverest challenger or the safest incumbent. It is being able to hold any of them to a result, on your numbers. Look again at why Gartner thinks so many of these projects die: Not the technology — cost, fuzzy value, weak controls. Our side of the table. So, start there. Take one high-volume, measurable workflow, pilot it against a baseline you own, instrument it with your own metrics, and treat the muscle you build doing that as the real deliverable. Get it right and the pricing model stops mattering. Skip it, and you have just agreed to pay for someone else’s definition of done.

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Seventy-one percent of organizations say AI has access to core business systems. Only 16% govern that access effectively, according to the 2026 CISO AI Risk Report. Ask your IR team three questions: Where is your AI system inventory? What happens if a production model starts generating harmful outputs? Who has the authority to take it offline?

I’ve spent 14 years in security — energy, banking, telecom, manufacturing. Red team work, detection programs and the last several years focused on AI risk and ShadowAI. What I see consistently: Organizations have AI in production, they have an IR playbook and they think those two things are connected. They’re not.

The CISO who thinks their IR playbook covers AI incidents probably hasn’t tested it. The ones who have tested it know it doesn’t.

Two kinds of AI incident — and why that split matters more than the list

AI incidents surged 56.4% from 2023 to 2024, reaching 233 documented cases. Most IR frameworks — including NIST SP 800-61, MITRE ATLAS and the GLACIS AI Incident Response Playbook — provide you with a taxonomy of six incident types and stop there. While useful, it misses the more important split: Failures the model causes on its own, versus failures caused by a human. Your detection approach, your containment logic and your legal exposure are very different between those two groups.

Model-originated failures — degradation, bias, hallucinations — happen when the system does exactly what it was built to do, just badly. The Epic Sepsis Model, deployed across hundreds of US hospitals, had a sensitivity of only 33% at external validation. It missed two-thirds of actual sepsis cases and flooded physicians with false alerts, as a 2021 JAMA Internal Medicine study found. No one attacked it. It just quietly stopped working while every dashboard stayed green.

Externally induced failures — adversarial attacks, data poisoning, privacy breaches — happen when someone corrupts the inputs or the training environment. Tesla’s Autopilot phantom braking cases, investigated by NHTSA across hundreds of thousands of vehicles, show what adversarial input failures look like in a safety-critical system. These two groups need different primary defenses and their own playbooks.

Then there is the hybrid case, which carries the most legal exposure right now. Hallucinations are model-originated but they land in court like human errors. When Air Canada’s chatbot invented a bereavement fare policy, the airline was held liable. When a US federal court let Mobley v. Workday proceed, it accepted that an AI hiring platform could be directly liable as an ‘agent’ of the employers using it. Neither failure looked like a security incident. Both ended up as legal ones. If your legal team is not on your IR call tree, your playbook is already incomplete.

The CIA triad doesn’t cover a hallucination

The CIA triad — confidentiality, integrity, availability — does not apply to most AI incidents. When Air Canada’s chatbot made up a policy, nothing was unavailable, nothing was changed without authorization, nothing was disclosed. The framework simply doesn’t reach it. When the Epic Sepsis Model missed two-thirds of cases, there was no breach, no intrusion, no indicator of compromise. By every traditional IR metric, the system looked fine.

This is not an edge case. Classical IR frameworks assume deterministic failures with static indicators of compromise — an assumption that breaks down against probabilistic systems. Microsoft’s Security Blog said it well in April 2026: A model may produce harmful output today and something completely different from the same prompt tomorrow. The root cause is not a line of code. It is a probability distribution, and as Microsoft’s Security Blog put it, you cannot patch a probability distribution.

The numbers confirm the gap. Average AI incident detection time is 4.5 days. Sixty-seven percent of AI incidents come from model errors, not adversarial attacks — yet security budgets keep funding perimeter tools built for the latter. We are looking for the wrong signals, with the wrong tools, for the wrong failure modes.

What a mature AI IR capability looks like

I get asked this at every conference I speak at. Here is the short answer: Three things that mature teams have in place before any incident occurs.

First, an AI Bill of Materials (AIBOM) for every production system. Think of it like a software SBOM, but for AI: It documents the base model, training datasets, third-party dependencies and the full component stack. Without it, you don’t know what your AI is made of — and you can’t investigate a data poisoning incident or a supply chain compromise without that baseline. The OWASP GenAI Security Project released an open-source AIBOM generator in December 2025 that produces output in CycloneDX format aligned with SPDX standards. It is practical to implement now.

Second, a model card for every production AI system — not a document in a shared drive nobody opens, but something your IR team can pull up in the first ten minutes of a response. Training data provenance. Model version. Known performance limits, including which subpopulations showed weaker accuracy in testing. Access controls. Blast radius if it fails. Most organizations I work with have model documentation written for data scientists that no one in security can use at 2am. That is not documentation. That is liability.

Third, a named data scientist on the IR call tree. Not someone to brief after the incident — someone with authority to interrogate model behavior in real time. Traditional IR has a network engineer on call. AI IR needs the same logic applied to the people who understand how the failing system works.

A fourth thing that very few teams have: A documented rollback threshold for each deployed model. A pre-agreed definition of what anomaly rate, drift metric or fairness deviation triggers containment or a fallback switch. Teams without this spend the first hours of an AI incident debating whether what they are seeing is actually a problem. Teams with a threshold spend those hours responding.

Four things to do before the next incident

Rewrite your detection triggers. Output anomaly scoring, data distribution monitoring for drift and behavioral tracking of model API usage need to be in your detection layer. They will not come from your SIEM. This is instrumentation work at the AI system level.

Redefine containment. For most AI incidents, ‘isolate the system’ is the wrong first move. Switching to a rule-based fallback while keeping the service running may cause less harm than taking the system offline and triggering a business escalation. Each deployed model needs pre-defined rollback criteria and a named fallback. Write those down now.

Get legal in the room before the incident. Mobley v. Workday means both the AI vendor and the deploying organization can carry liability for bias incidents. Air Canada means you cannot disclaim what your AI says to a customer. If your legal team is learning about an AI incident from a press inquiry, something has already gone wrong.

Build your AI inventory and treat it like your asset register. Start with the AIBOM for your highest-risk systems — those with access to customer data, financial decisions or clinical workflows. The GenAI-IRF framework gives you a structured taxonomy for this work and the GLACIS AI Incident Response Playbook maps it to NIST SP 800-61 and MITRE ATLAS procedures your team can adapt without starting from scratch.

Forty-two percent of organizations have already had a suspicious or confirmed AI incident, and more than half say their security posture is catching up, inconsistent or reactive. Updating your playbook isn’t optional. Fix it before you need it.

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A product manager on my team recently asked me where we were seeing the most issues across the engineering team. Instead of guessing, I had an engineering lead point Claude at our Jira via an MCP connector and look at the bug patterns himself.

One team had a wildly disproportionate share of tickets — about 50% of their sprint time was spent on “bugs,” versus roughly 25% for everyone else. The headline number suggested a quality problem.

It wasn’t. When we layered in the context around those tickets, almost none of them were bugs. They were manual workarounds for a missing product capability: customers asking us, one request at a time, to restore items they had accidentally deleted. Not shipping an item restore feature was burning roughly 1.5 engineers’ worth of capacity. I went back to our product team and said, “Build this, and you reclaim a person and a half.”

The analysis took 45 minutes. It was only possible because our data was already organized, tagged by team, connected to contributors, accessible through MCP and protected by role-based access. None of that is “AI.” All of it is the layer underneath AI that almost nobody invests in first. That’s probably because the investment is unglamorous: updating data dictionaries, access controls, team taxonomies, system-to-system mappings. Most of the work has been the same for twenty years. AI just raised the cost of skipping it.

The intelligence underneath the models

I keep coming back to the value of context data layers as a CTO in the middle of an AI rollout. I have started calling that value proposition contextual intelligence because I haven’t found a better name. Anthropic’s engineering team has been calling this kind of work “context engineering” since late 2025, and CIO ran its own feature on the term shortly after. Whether you describe it as contextual intelligence or context engineering, it’s the part of the stack where the actual programming work still lives.

If business logic is your company’s official org chart, then contextual intelligence is knowing who actually gets things done, how decisions are actually made and what the unwritten rules are. One is theory. The other is reality.

Most enterprise systems capture the theory. The systems that capture how work actually happens — what people do, how teams operate, where decisions get stuck — are rarer and harder to build. And modern LLMs, it turns out, are useless without both.

I learned this the hard way at a recent company hackathon. Nine engineering teams, one prompt: make our operational dataset more usable through AI. My team built persona-based chatbots (CFO, CIO, sales manager) on top of an MCP server backed by Postgres and our enrichment data. Other teams built dashboard generators, Looker conversational analytics and workflow agents.

The initial demos all had the same problem. Claude could talk to our data, but the answers were either generic or confidently wrong. The CFO persona would happily report a “spend trend” that quietly conflated two distinct cost categories across two different tables. The CIO persona would answer questions about team productivity, but the averages across roles should never have been aggregated. The sales manager persona returned answers that were technically correct against the schema and completely wrong against the business. The raw data was rich. The context layer around it didn’t exist yet. Chatting with raw data is not an AI product. It’s a demo.

One of my senior engineers spent the second day ripping out the agent’s direct database connection. He stopped trying to prompt-engineer the LLM to understand our business and instead codified that logic into the data pipeline. Working backward from the failed CFO answers, he mapped out the implicit knowledge an experienced controller relies on: Explicitly defining which legacy tables actually represent ‘spend,’ writing the rules for currency normalization and hardcoding our fiscal time windows. He built a series of semantic SQL views to enforce these rules and restricted the MCP server to exposing only this curated layer. When we pointed the same model at those same questions, it returned completely different answers. They were specific, evidence-based and grounded in our actual business reality. The model didn’t get smarter. The engineering beneath it did.

The same pattern shows up everywhere I look right now

McKinsey keeps publishing that software development tops enterprise AI use cases, with companies reporting 30–50% productivity gains in pilots. The pilot numbers are real. They rarely translate to top- or bottom-line impact in production. Our own company data tells the same story: Between Q1 2025 and Q1 2026, our total AI tool usage grew by 328% (over 4x). Over that same period, PR throughput grew by just 49%.

That gap — adoption way up, outcomes inching along — is the context gap. Plug a generic agent into raw, uninterpreted data, and it will act inefficiently at best, harmfully at worst. An agent optimizing sales without your customer segmentation or product hierarchy will confidently recommend the wrong thing. Anthropic framed the shift directly: building with language models is becoming “less about finding the right words and phrases for your prompts, and more about answering the broader question of what context configuration is most likely to generate our model’s desired behavior.” That second question — what context configuration  — is the entire game. Most organizations are still answering the first one.

Where the work actually lives

A growing number of CTOs I talk to are shifting their AI investments accordingly. Less attention on the model. More on the layer between the model and the data.

When peers ask me what that actually looks like day-to-day, I tell them I give every engineering role the same mandate: the LLM should never see raw, uncontextualized data.

In practice, that breaks down to three pieces of work, none of them glamorous.

The first is semantic middleware. We need code that transforms raw data into business-meaningful signals before it ever reaches the model. Our feature stores hold things like “employee code velocity on critical-path features,” not “X logged 50 Git commits.” The work of figuring out what “critical-path” means in our product, in our org, on this team is the work. It does not get cheaper because the model has gotten better.

The second is multi-agent design. Instead of one omniscient orchestrator, we run smaller agents scoped to specific domains, each with rules that catch the failure modes the main model is known for. We pair them with RAG that retrieves precomputed insights, with their rules attached, rather than raw documents. Validation checkpoints sit between steps and flag suggestions that violate known constraints, such as averaging productivity across completely different job functions. The guardrails are not there to be clever. They are there because we already watched the model make those exact mistakes.

The third is evaluation that takes business logic seriously. When I look at a model, general benchmark accuracy is the least interesting number. I want to know whether it respects our constraints and integrates cleanly with our existing architecture. That sometimes means fine-tuning our patterns, sometimes constitutional approaches to embed principles, sometimes hybrid systems where deterministic rules sit alongside the probabilistic ones. The throughline is the same: validate against reality, not against the benchmark.

Why this matters now

The reason this matters more now than it did six months ago is that adoption is moving faster than measurement, let alone integration. Model Evaluation & Threat Research’s (METR) developer productivity work tells the story in a way they didn’t intend. In early 2025, they ran a controlled study and found AI tools slowed experienced open-source developers by 19%. When they tried to repeat the study in late 2025, the experiment broke. Thirty to fifty percent of developers refused to submit tasks under the no-AI condition. They wouldn’t accept working without their tools. METR is now redesigning the study because the original methodology no longer holds up against how developers actually work. That’s how fast adoption moved. But I’d be willing to bet the organizational scaffolding required to convert that adoption into outcomes — context layers, workflow redesign, retraining around new tools — moved nowhere near as fast.

Get ahead with context

The teams I’ve seen succeed with AI built the context layer first. The teams I’ve seen struggle eventually built in context anyway, just at higher cost and with more scar tissue. Raw data is the new currency. But raw data without a context layer is cash sitting in a vault. It cannot act on anything. The difference between insight and noise is a layer of code that understands what your data means.

That layer is the work. It is where the next decade of competitive advantage will sit. And in my experience, the organizations that build it first are the ones that will actually get the productivity gains the rest of the market keeps promising.

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Picture the moment after an AI issue is reported.

A security analyst is reviewing a ticket reporting that an internal AI tool produced the wrong recommendation in a live business workflow. The risk is not theoretical anymore. Someone wants to know whether this is a security incident, a model issue, a privacy issue, a vendor issue or just “something the AI did.” The risk register has a line item for inaccurate output, and it may even have a severity rating.

What it does not have is an answer to the question everyone is now asking: who has the authority to stop this thing?

That is the gap many AI governance programs still need to close. Organizations are getting better at identifying AI risks, documenting them and assigning them to governance categories. What they are often less prepared for is the operational moment when an AI risk becomes a real event that has to be investigated, contained and explained.

In security programs, that distinction matters. A risk register can document concerns, but it cannot preserve evidence, notify leadership, assess impact or decide whether an AI system should keep running. Security leaders do not need another spreadsheet that says AI can fail; they need an executable response model for what happens when it does.

The list is not the response

Risk registers are useful because they create visibility. They help organizations name risks, compare severity, assign ownership and communicate concerns to leadership. In early AI adoption, visibility matters because many organizations are still discovering where AI is being used, what data is involved and which business processes may be affected.

But a risk register is not a control. Security teams already understand this in other domains. A list of vulnerabilities is not a vulnerability management program, and a list of third-party risks is not a vendor risk management function. The list is only the beginning of the work.

AI risk creates the same problem. A risk entry that says “model output may be inaccurate” does not define who monitors output quality, what level of error is acceptable, what evidence should be preserved or who can pause the system. A risk entry that says “sensitive data may be exposed” does not explain whether prompts are logged, whether outputs are reviewed, whether the vendor can use submitted data or whether the event should trigger privacy, legal or security escalation.

This is where AI governance can look stronger than it actually is. The organization may have a policy, a committee, an intake form and a risk register, but those artifacts do not automatically create operational readiness. When something happens, the real test is whether the organization knows what to do next.

AI incidents do not always look like breaches

Part of the challenge is that AI incidents do not always look like traditional cybersecurity incidents. A breach has familiar patterns: unauthorized access, data exfiltration, malware, credential compromise or suspicious activity in a system. AI failures can be messier because they may appear first as a bad recommendation, a misleading summary, an unsafe automation, a flawed classification or an output that quietly changes a decision.

That does not make them less important. An AI tool used in a security workflow could misclassify an alert. A generative AI assistant could expose sensitive information in a response. A model embedded in a business process could drift over time and produce unreliable recommendations. A vendor-managed AI feature could change behavior after an update that the organization did not fully review.

Security teams need a practical way to sort these events. Not every AI error should be treated as a full security incident. Still, every organization using AI in meaningful workflows should know how AI-related events are reported, triaged and escalated. Without that structure, teams may lose time debating ownership while the impact continues.

The first step is defining what counts as an AI incident. That definition should be broad enough to capture security, privacy, safety, operational and compliance concerns, but specific enough that employees know when to report something. A confusing chatbot answer may not require the same response as a data exposure event, but both should have a path for review.

Evidence has to exist before the investigation

Incident response depends on evidence. That is obvious in cybersecurity, but it is often overlooked in AI governance conversations. If an organization cannot reconstruct what happened, who used the system, what data was involved and what output was produced, it will struggle to investigate the event or defend its response.

AI systems can complicate that evidence trail. Prompts may not be logged. Outputs may not be retained. Vendor tools may provide limited visibility. Model versions may change. Users may copy AI-generated content into other systems without preserving its source. Business teams may treat AI output as a recommendation rather than a system event.

Security leaders should push for evidence requirements before AI systems move into production. At a minimum, organizations should know what logs are available, how long they are retained, who can access them and whether they are sufficient for investigation. For higher-risk use cases, teams may also need records of model version, prompt history, output history, user actions, data sources and downstream decisions.

This does not mean every AI interaction needs heavy surveillance. Monitoring should be proportional to risk, and organizations still need to respect privacy, legal and workforce considerations. The point is simpler: if the AI system matters enough to influence real work, it matters enough to leave an evidence trail when something goes wrong.

Ownership cannot be implied

AI ownership is often fragmented. A business unit may sponsor the use case, a data science team may configure the model, IT may manage the platform, security may assess risk, and a vendor may provide the underlying capability. Everyone is involved, but no one may be fully accountable after deployment.

That ambiguity becomes dangerous during an incident. If an AI tool begins producing unreliable output, the organization needs to know who owns the system, who owns the business process and who owns the decision to continue or stop use. A governance committee can provide oversight, but it usually cannot serve as the operational owner of every deployed AI capability.

Security programs should insist on named ownership for AI systems, especially those used in sensitive or high-impact workflows. Ownership should include responsibility for monitoring, exceptions, user guidance, vendor coordination and incident escalation. It should also include decision rights, because accountability without authority is just a name in a spreadsheet.

The hardest question is often pause authority. Who can suspend, restrict, roll back or retire an AI system when risk exceeds tolerance? If that question is not answered before deployment, the organization may be forced to answer it under pressure.

Security leaders need an AI response playbook

An AI response playbook does not need to be complicated, but it does need to be real. It should explain how employees report AI concerns, how the event is triaged, what evidence is preserved, who investigates, when legal or privacy teams are involved, and who can make operational decisions. It should also define when executive leadership needs to be notified.

The playbook should reflect the type of AI system involved. A low-risk internal productivity tool may require a lightweight review path. An AI system supporting security operations, regulated decisions, customer communication, healthcare workflows or financial processes needs stronger monitoring and escalation. The response model should fit the risk of the use case.

This is where security can add discipline without turning AI governance into bureaucracy. Security teams already know how to build escalation paths, preserve evidence, run incident reviews and improve controls after failures. The opportunity is to extend that operating muscle into AI governance before incidents force the issue.

Organizations should also conduct post-incident reviews for meaningful AI events. The goal should not be blame; it should be learning. Did the monitoring work? Was the owner clear? Was the evidence sufficient? Did the vendor respond? Were users confused about acceptable use? Did the organization know who could make the decision?

Governance has to be executable

AI governance is often discussed as a policy, ethics or compliance challenge. It is all of those things, but once AI systems enter production, it also becomes a security execution challenge. Risk has to be monitored, events have to be investigated and someone has to be able to act.

That is why the next maturity step is not simply better documentation. Organizations need governance that works when a system is live, a decision is time-sensitive and the facts are incomplete. In that moment, the risk register may help explain what the organization expected, but it will not run the response.

Security leaders should not wait for AI governance to arrive fully formed from somewhere else in the enterprise. They should help shape the operating model now, while many organizations are still early enough to correct course. The goal is not to own every AI risk; it is to ensure AI risk can be managed once AI becomes operational.

A risk register can tell leaders what might go wrong. An incident response plan tells people what to do when it does. For AI governance to matter in security programs, organizations need both.

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Intro

• Consumers across APJ are getting more impatient. They expect brands to resolve their issues in just 24 minutes on average.
• If the brand is unsuccessful, 34% say they’ll switch channels to find a faster path to resolution, and 30% say they’ll abandon the effort altogether.
• Most leaders reading this insight would respond by improving agent response times, but speed isn’t the problem. The crux is that consumers want a solution, not to wait less.
• Unfortunately, the AI that most brands have deployed are chatbots who try to handle everything (and then fail).
• What we’re seeing is the opposite. The most productive agents aren’t generalists, but specialists who excel at one thing and know when to hand off when they can’t handle something.
• This intelligent orchestration is a superpower.

The cost of sending customers in circles

• 90% of business leaders believe their customers are satisfied with conversational AI, but only 59% of consumers agree.
• 54% of consumers say AI agents rarely or never have context about them as a customer.
• 78% say it’s important to be able to switch from an AI agent to a human, yet only 15% report experiencing seamless handoffs.
• Most escalations involve lost context, repeated explanations, and restarted conversations. Every misroute doesn’t just waste one interaction—it triggers a cascade. The customer calls back, a second agent asks the same questions, trust erodes, and the next interaction starts from a deficit.
• It’s no wonder that 42% of consumers say AI makes them less patient, not more. 41% are satisfied with how brands currently use AI.
• For customer service teams, the real challenge is routing, not tech.

What self-service really needs

• Brands need four capabilities for self-service AI agents to work.
  • 1. Agency: Specialised agents that can handle defined tasks with precision and don’t attempt everything and resolve nothing.
  • 2. Always-on monitoring: The system must monitor interaction quality in real time and catch failures before they compound into callbacks.
  • 3. Real-time contextual data: Agents must have a unified view of the customer, including history, intent, and recent interactions.
  • 4. Intelligent routing: The system must accurately decide in the moment whether a task stays with AI, moves to a specialist, or escalates to a human with full context.
• Of these four, routing is the most underinvested and the one that determines whether the other three deliver value.

Routing is the intelligence layer

• Think of routing not as plumbing but as decision-making.
• A well-designed system evaluates task complexity, required skills, customer history, sentiment, and more before matching it to the right resource.
• For example, a complex billing dispute will be routed to a senior billing specialist, not the next available generalist. A routing appointment request stays with the AI agent that can solve it in seconds.
• When the AI encounters an edge case it can’t handle, the routing layer transfers the task, along with full context, so the next agent can pick up where the AI left off.
• Twilio’s own research confirms this. 42% of consumers prefer starting with a human agent, even if it takes longer, while 23% are comfortable starting with AI and escalating when needed.
• Both paths demand routing intelligence. The AI-first customer needs seamless escalation, and the human-first customer needs to reach the right human immediately. Neither can afford a misroute.

When resolution compounds

• Every issue resolved on first contact is one fewer repeat call in the queue.
• Fewer repeat calls mean shorter wait times for everyone.
• This compounding effect extends to agent capacity. When routing works, human agents are freed from solving issues that should have been addressed the first time. They spend their time on complex, high-value interactions instead.
• This is what 72% of consumers are signaling when they say they’d choose AI over a human if the issue was guaranteed to be solved faster.
• 46% of consumers say quick service and resolution are their top priorities, and 51% say delays are acceptable if they lead to better customer support.
• Patience is available but only when the brands earn it by sending customers to the right place the first time.
• The brands that treat routing as an afterthought will keep optimising for speed and see their customers quietly leave. Those who optimise for resolution will build trust that compounds with every interaction.

To learn more about Twilio, visit here.

The threat that I now spend most of my time designing against doesn’t look like a breach at all. At least not at first.

Imagine a team deploys an agent that does exactly what it’s permitted to do: it reads a customer record, summarizes it, then sends the summary to an outside address. Every step in the sequence is authorized. But it turns out that the breach is the sequence itself.

The problem is that each security check only looks at one step at a time. Is this read okay? Yes. Is this summary okay? Yes. Is this email okay? Yes. Each step passes. But nobody is watching the combination of all three steps together. The security tools designed for human-driven workflows assumed a person would be doing this manually, one thing at a time. However, the AI agent bundles it all into a single automated sequence, and that bundling slips through gaps between the checks.

I build authorization for agentic systems, and the gap between “every action was allowed” and “the outcome was a breach” is what I keep coming back to.

An agent is not a user or a file. It is an insider authorized with an API token instead of a badge to act on your behalf. We learned decades ago that perimeters don’t secure against insiders. But in the design reviews I’ve sat in this year, the security conversation still centers on prompt injection and output filtering. That’s one layer below where the exposure has moved.

Two decades of asking the wrong two questions

We spent 20 years getting very good at two questions:

• Who is allowed in?
• What data is allowed out?

Identity and access management answered the first question. Data loss prevention the second. Both assume a world of users and files—a human you authenticate at the door and a document you inspect on the way out. But production AI agents make both questions obsolete.

An agent is an actor. It reads context, chains tool calls, invokes connectors and changes systems of record, then hands work to other agents as it goes. The danger isn’t that it does one clearly forbidden thing; it’s that it does a series of small, permitted things that add up to something harmful. And because each individual action looks fine, the standard security tools don’t flag anything. It’s the same reason an employee with legitimate access is harder to catch than an outside hacker.

This is a known failure mode in IT security, sometimes called the confused deputy problem: a program with legitimate authority gets manipulated into misusing it on someone else’s behalf. Now, AI agents have given it initiative. An agent is a confused deputy that doesn’t just hold authority but plans with it. The OWASP community ranks excessive agency—an agent operating with broader capability than its task requires—among the top risks for large language model applications.

The four ways agent authority goes wrong

When I threat-model an agent before it ships, four failure modes do most of the damage, and the governance conversation most teams are having addresses none of them.

1. Tool-chain abuse. Each tool call is safe on its own, but the chain composes into something no one authorized. The pattern is mundane: an agent permitted to read records, call a summarizer and send mail turns those three benign capabilities into a clean exfiltration path. Content filtering inspects each step and waves all of them through, because no single step is prohibited.

2. Delegation-chain exploitation. An agent hands a subtask to another agent, and the child ends up with authority it was never meant to have. The mechanism is simple: the parent passes the child a copy of its own credentials, so the child can now do everything the parent can. Most orchestration frameworks pass parent context down by default because they assume the child is trusted. That’s a framework default, not a security decision.

3. Approval evasion. A human-in-the-loop gate is supposed to catch the consequential action, but the agent reaches the same outcome by a path the rule didn’t anticipate. This isn’t agents being clever; it’s policies written for human workflows. A gate that checks “summarizing customer records” is blind to an agent reaching the same data by another tool path. In other words, it guards the actions humans take, not the outcome it was meant to protect.

4. The first three are how the breach happens. The fourth is why it becomes a crisis: audit opacity. Even after you discover something went wrong, you can’t piece together the full picture: what exactly the agent did, who authorized it to do those things or whether it went beyond what it was supposed to do. The logs simply show that reads and sends happened. Only in the post-incident review do teams discover their logs were written for debugging, not for proof.

Move the decision to runtime

When these failure modes surface, the instinct is to add another detection layer, such as a better filter or a smarter classifier watching the output. That instinct is wrong. You can’t inspect your way out of a problem of authority. The answer is a runtime policy engine that governs what an agent is allowed to do at the moment it acts.

The concept isn’t new; it’s zero trust, applied inward. We spent years pushing zero trust outward to the perimeter for people and devices. Every request is authenticated and authorized in context, decided centrally rather than assumed at the edge. Agents move the object of that decision inward, from who are you at the door to what will you do in the next call.

A runtime policy engine makes that concrete. It evaluates which tool is being called, which data is being touched and what the downstream effect will be.

Three properties make it real:

1. Decide before the action fires. Evaluate the agent’s intended action against policy and live context at call time, not afterward in a log review. A policy that isn’t evaluated at the moment of action isn’t a control.

2. Make delegated authority shrink. Authority should only narrow as it passes from agent to agent, never widen. That way, a compromised agent can’t exceed the narrowest link in its chain, and stopping a parent leaves no orphaned authority downstream. Capability can still be re-requested; a child can ask its parent to escalate, but that escalation is evaluated and logged at call time, not baked into a token handed over once.

3. Build audit as evidence, not logs. Evidence means a record that ties each action to the policy that authorized it—principal, tool called, inputs, the rule evaluated, the decision and a timestamp—in append-only or signed storage so it can’t be quietly rewritten. It lets a regulator or a board reconstruct who acted, on whose authority and whether that authority was exceeded, instead of relying on a forensic reconstruction weeks later. Most deployments skip this because it’s infrastructure work, not policy work.

One implementation caveat: Evaluating every action at runtime adds latency and demands live policy context. Some friction is unavoidable, so the question is where you add it. Focus on the actions where a mistake is hardest to reverse: Anything touching customer data, financial systems or infrastructure.

The three questions I ask before every deployment

When a team brings me an agent bound for a real system of record, I’ve stopped asking which model it uses. I ask three things instead:

1. Can every action resolve to a human source of authority, captured at runtime?

2. Does the agent’s authority shrink as it delegates, or can a subagent do more than its parent?

3. If this agent did something wrong tomorrow, could we prove what it did? (Not describe it. Prove it.)

The autonomy that makes AI agents so valuable also makes legacy controls insufficient. You can’t add autonomous agents to your existing processes and expect last year’s controls to cover them. When an agentic breach happens, the question the board asks won’t be, “What leaked?” It will be, “What was your agent allowed to do, and can you prove it?”

Get ahead of it before the board has to ask.

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Microsoft is warning defenders about a new backdoor that blurs the line between espionage malware and wipers.

In a technical analysis published on Thursday, Microsoft Threat Intelligence detailed GigaWiper, a Golang-based implant first observed in October 2025 intrusions that combines remote administration capabilities with multiple disk-wiping and ransomware routines.

Rather than building a new destructive tool from scratch, the operators assembled GigaWiper from several existing malware families, embedding them as modular commands inside a single backdoor.

“GigaWiper is particularly notable for its makeup,” Microsoft researchers said. “The consolidation of multiple destructive capabilities into a modular backdoor reflects a notable shift in wiper malware, which are typically designed purely to destroy rather than to extort and carry real-world consequences.”

Malware capabilities of the backdoor included multiple disk wiping logics, an irreversible Crucio ransomware encryption, persistence, and RabbitMQ and Redis-based communication.

A backdoor for destruction on demand

According to Microsoft, GigaWiper exists in two forms. A standalone wiper and a larger backdoor whose command set embeds the standalone wiping functionality alongside numerous administrative features.

Written in Go, the malware supports 20 command codes that enable operators to execute PowerShell commands, manage Windows services and processes, manipulate the registry, capture screenshots, record displays, clear event logs, and remotely control infected systems through a Virtual Network Computing (VNC)-like capability.

Persistence is established through a scheduled task posing as a “OneDrive Update,” while command-and-control (C2) relies on RabbitMQ for receiving instructions and Redis for returning command output. This architecture allows attackers to quietly maintain access and selectively activate destructive functionality when an objective has been achieved, the researchers added.

The backdoor combines three malware families

Microsoft researchers found that GigaWiper integrates destructive code from multiple malware families instead of relying on a single wiping mechanism.

These integrations show up in the form of separate commands that the backdoor supports.

One command performs raw physical disk wiping by overwriting drives and removing partition metadata. Another borrows from the Crucio ransomware family, encrypting files with randomly generated keys that are intentionally never stored, making recovery impossible despite presenting itself like ransomware.

A third command recreates the functionality of FlockWiper, implementing secure multi-pass wiping in Go to permanently erase data on Windows systems.

“We tied GigaWiper to both Crucio and FlockWiper based on code analysis, shared execution flow, function naming, and unique strings,” the researchers said. “Crucio’s code was the base for GigaWiper command 3, and FlockWiper was re-coded in Golang and updated for GigaWiper command 12,” they noted, referring to the 20 listed commands the backdoor supports.

The standalone wiper was implemented as command 1 from the list.

Microsoft recommended hardening endpoints and identities, enabling behavioral detection and endpoint detection and response (EDR) capabilities, and using attack surface reduction controls to limit compromise risks.

The company also urged defenders to maintain offline or otherwise resilient backups, as destructive malware like GigaWiper is designed to irreversibly wipe or encrypt data. To support detection, the researchers shared a list of indicators of compromise (IOCs), which included FlockWiper and Crucio file hashes and a couple of C2 IP addresses.

For those who wonder what the support window is for Apple products, the company now has an answer: it’s quietly ended support for some of its oldest iPhones and iPads, cutting off restore access for devices that first went on sale more than a decade ago. 

While the move has prompted some complaints, the truth is that it underlines just how unusually long the company has kept aging hardware alive. Even today, it provides support in the form of access to signed software upgrades for non-cellular devices as old as some teenagers. 

What devices have been cut?

Among other things Apple has cut support for a range of older cellular-equipped devices, as it no longer supports the modems. Take the iPhone 4S, introduced about the same time iconic Apple CEO Steve Jobs died. Apple has stopped signing iOS versions for that device, which means if you’re still running one, you won’t be able to restore or downgrade to several older iOS versions on it. 

This isn’t the only older system for which Apple has stopped signing versions, but all these newly abandoned products are 12-years old, or older. Affected devices include the iPhone 4, iPhone 4S, iPhone 5, iPhone 5c, iPad 2, iPad 3, iPad 4 and the original iPad mini. In each case, if you have an iPad without a cellular modem you should still be able to reinstall OS software, but cellular devices are abandoned. They’ll continue to work; you just can’t reinstall the operating system in the event of a problem.

The specifics are telling. The cut affects iOS builds like 6.1.3, 8.4.1, 9.3.5/9.3.6 and 10.3.3/10.3.4 — versions tied to the original iPad 2, iPad mini and iPhone 5c. One of those, iOS 10.3.4, was actually a special one-off patch Apple pushed out just for the iPhone 5 to fix a GPS bug tied to the GPS week rollover, underlining just how much engineering effort Apple still throws at older devices.

Why it kind of matters at the same time

The move to cut support is unlikely to cause any significant problems, as only a tiny number of these devices will be in active use. Some developers might use old devices for compatibility testing, though, and by making this move Apple is obviously telling developers to constrain their legacy device support. It’s also a reasonable piece of housekeeping: maintaining signing servers for decade-old, security-patched builds isn’t free. (Apple frames these moves as closing off outdated software that could expose old vulnerabilities.)

How does this compare with others?

Apple has always had a good reputation for product support; in part, this is why its devices maintain such strong resale values over time. That commitment became more explicit in 2024 following UK regulation, after which it now guarantees at least five years of security updates. Around the same time, Google and most big Android device manufacturers went a little further, committing to seven years of security and operating system updates. 

Smaller manufacturers don’t always match this commitment; in some cases, you might find similar support for budget Androids can be as short as two years. It’s also worth considering the user experience when working with older Android devices. While Apple’s tight software and hardware integration tends to support high-value user experiences, the more fragmented nature of the Android manufacturing process means some devices don’t offer the same degree of usability when older. Pixel’s Tensor have drawn criticism for struggling to run smoothly as they age, even if they’re still technically supported.

What this means is that Apple continues to under promise and overdeliver on its support commitment to older devices — so much so that it’s only now some customers who might still be running a 15-year-old iPhone have finally hit the support wall. 

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