With us today is Rupert Marais, our in-house security specialist whose expertise in endpoint security and network management gives him a frontline view of the challenges facing corporate IT. We’ll be delving into the increasingly chaotic world of Microsoft’s patching cycle, exploring the real-world impact of the now-commonplace “emergency” updates on system administrators. We’ll touch on the difficult choices this new reality forces upon IT teams, the hidden productivity costs of flawed patches, and the potential role that new development practices, including AI, might be playing in this disruptive trend.
Early 2026 saw two emergency updates shortly after Patch Tuesday. How does this increasing frequency of out-of-band patches affect an administrator’s weekly planning, and what new challenges does it create for managing large fleets of Windows devices?
It’s completely shattered the rhythm we used to rely on. Patch Tuesday was once a predictable event; you’d block out time for testing, plan your deployment waves, and communicate a clear schedule. Now, that structured plan feels almost pointless. The start of 2026 was a perfect example; we’d just finished our post-Patch Tuesday deployments when the first OOB dropped, and then another. It forces us into a reactive, almost constant state of alert. You’re constantly checking release health dashboards and security bulletins, and the planned project work for the week gets pushed aside to deal with an emergency deployment that wasn’t on anyone’s radar 24 hours earlier.
Microsoft historically reserved out-of-band releases for “atypical” cases. Now that they seem to follow almost every major update, how should IT teams adjust their risk assessment? What is the new calculus when deciding between patching a vulnerability immediately versus waiting to avoid a showstopper bug?
The calculus has become incredibly fraught with tension. On one hand, you have the CISO and the security team pushing for immediate deployment to close a critical vulnerability. On the other hand, you have the ghost of past updates that have crippled business operations. The risk assessment is no longer a simple binary choice. We now have to weigh the known, documented risk of a security exploit against the unknown, but statistically likely, risk of a business-breaking bug in the patch itself. Many experienced admins are now building in an unofficial “soak time,” holding off on even critical patches for a few days, which feels like a dangerous game to play. It’s a gut-wrenching decision between leaving the door unlocked for a night or risking the new lock jamming and trapping everyone inside.
These emergency fixes have impacted everything from Windows Server to older systems like Windows 10. Can you walk us through the real-world productivity costs of a botched update, detailing both the user downtime and the administrative overhead required to deploy a subsequent out-of-band patch?
The costs are staggering and go far beyond a simple reboot. Imagine a patch rolls out and breaks a critical function on Windows Server 2022. Suddenly, an entire department’s core application is down. That’s immediate, quantifiable productivity loss for dozens, maybe hundreds, of employees. The help desk phones light up, and my team has to drop everything to investigate, verify the issue, and potentially roll back the update, which is another disruptive process. Then, when Microsoft releases the OOB fix, we have to start the entire change management and testing process all over again. All that administrative faffing around—testing, scheduling, deploying, verifying—is time we’re not spending on strategic projects.
This trend has coincided with reports that AI contributes to over 30% of new code. What are the potential connections between increased reliance on AI in development and a decline in initial patch quality? How might this be changing traditional software testing and validation cycles?
It’s hard to ignore the timing. While we can’t draw a direct line of causation, the correlation is concerning. When a CEO boasts that over 30 percent of new code is AI-assisted, and at the same time we see a sharp decline in the stability of that code, it raises serious questions. It feels like the push for AI-driven development speed might be outpacing the evolution of testing methodologies needed to validate that code. Traditional testing often relies on predictable human logic and error patterns. AI-generated code might introduce entirely new, “atypical” failure points that legacy testing simply isn’t designed to catch. It seems plausible that we are seeing the direct result of a quality assurance gap, where the code is being written faster than it can be properly vetted.
As administrators face this new reality, some have begun referring to these fixes as “OOPs” or Out-of-Patch-fixes. What strategies or best practices can IT departments implement to better anticipate and mitigate the disruption caused by this cycle of patches followed by emergency fixes?
The “OOPs” nickname is grimly accurate. Mitigation has become our primary focus. First, robust and segmented pilot groups are no longer a luxury; they’re an absolute necessity. You need to test every patch against a representative sample of your environment before it goes wide. Second, strengthening your rollback procedures is critical. You must have a tested, reliable way to uninstall a problematic update quickly. Finally, communication is key. We have to be more transparent with business leaders and end-users, managing their expectations that the patching process is now more volatile. We’re essentially building a new playbook for a reality where every official patch has a high probability of needing its own follow-up fix.
What is your forecast for Microsoft’s patch quality and release cadence for the remainder of 2026?
Given the trajectory we’re on, I feel a sense of dread rather than anticipation for the rest of the year. Satya Nadella’s statement that “2026 will be a pivotal year for AI” now sounds less like a promise and more like a warning to those of us in the trenches. I don’t see this trend reversing course anytime soon. I expect we’ll continue to see this pattern of a major Patch Tuesday release followed by one or more “OOPs” fixes. Until there’s a fundamental shift in Microsoft’s development and testing philosophy, or a significant financial or reputational consequence that forces their hand, administrators should brace themselves for this chaotic new norm to continue.
