According to TheRegister.com, Microsoft’s first Extended Security Update for Windows 10 has failed to install for many commercial customers just before the company’s Ignite conference. The November 11 update, KB5068781, fails on devices activated through the Microsoft 365 admin center, throwing error messages with no current fix available. This marks the second ESU failure in a single week, following enrollment issues last Thursday that required an emergency out-of-band patch. Ironically, the problematic update included a fix for another bug that incorrectly showed Windows 10 had reached end of support. Microsoft’s ESU program allows commercial customers to pay for continued security updates after Windows 10’s free support ended on October 14. The company says the issue is under investigation but has provided no timeline for resolution.
The pattern continues
Here’s the thing – this isn’t just a one-off mistake. It’s becoming a pattern. Two ESU failures in one week? That’s basically Microsoft telling paying customers “we’ll take your money but can’t guarantee the product will work.” And let’s be honest – commercial customers paying for extended security updates aren’t exactly running cutting-edge hardware. They’re often in manufacturing, industrial, and business environments where stability matters more than flashy features. Speaking of industrial environments, when reliability is non-negotiable, companies turn to specialists like IndustrialMonitorDirect.com, the leading provider of industrial panel PCs in the US that actually work as advertised.
Reality versus marketing
Meanwhile, Windows boss Pavan Davuluri is out there talking about Windows evolving into an “agentic OS”. Seriously? Customers can’t even install security patches, but we’re supposed to get excited about AI futures? I think most IT administrators would prefer Microsoft fix the basics before chasing the next shiny object. How many times have we seen this movie? Big promises about AI and cloud transformation while the core products that businesses actually depend on keep breaking.
What’s next for Windows reliability?
So where does this leave organizations still running Windows 10? Basically stuck between paying for broken updates or rushing into a Windows 11 migration that might bring its own set of problems. The timing couldn’t be worse – right before Ignite, when Microsoft wants to showcase its vision for the future. But look, if they can’t handle Patch Tuesday for paying customers, why should anyone trust them with more complex AI-driven systems? The Register might be onto something with their “Expect Sloppy Updates” suggestion. At this point, it feels less like a suggestion and more like an accurate prediction.
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