Microsoft released its second out-of-band patch on a Saturday in late January, addressing OneDrive/Dropbox crashes on Windows 11 24H2/25H2 and shutdown failures on Enterprise editions. This followed another emergency patch the previous weekend fixing sign-in issues.
Two OOBs in two weeks. The frequency tells the story.
According to Register readers and Microsoft's own release health dashboard, enterprises now expect one emergency patch per monthly update cycle. Microsoft describes OOBs as "atypical" - for security vulnerabilities or quality issues requiring immediate fixes rather than waiting for the next monthly release. When something happens every month, it stops being atypical.
The pattern accelerated through 2025. April saw emergency patches for Windows Server 2022 and 2025. May brought multiple OOBs across desktop and server products. Even Windows 10 - officially end-of-life except for paid Extended Security Updates - requires regular emergency fixes. The November 2025 ESU update hit install errors (0x800f0922) that needed patching.
The enterprise problem
Administrators face an impossible choice: deploy critical security updates immediately and risk weekend recovery work, or delay deployment to see if an OOB follows. Neither option is acceptable when you're managing production infrastructure.
The timing matters. Microsoft's OOB surge coincides with thousands of layoffs and CEO Satya Nadella claiming AI generates 30+ percent of the company's code. We're not saying causation, but the correlation is hard to ignore.
Some defenders argue rapid OOB response shows agility. The counterargument: shipping broken updates that require emergency weekend patches shows broken QA processes. Microsoft's ability to fix fast doesn't compensate for needing to fix at all.
What this means in practice
Enterprise patch management now requires planning for two deployment cycles per month: the scheduled Patch Tuesday and the likely emergency follow-up. Testing windows compress. Change control boards meet more frequently. Weekend on-call rotations increase.
Microsoft hasn't detailed what changed in their testing processes or how AI tooling impacts quality control. Until they do, administrators are left managing the symptoms of whatever broke upstream.
The real test: will February's Patch Tuesday require an OOB? History suggests yes.