No single OS feature touches more users than Windows Update. That alone should be enough incentive for Microsoft to make sure it works nearly perfectly. But time and time again, problems crop up, sometimes for millions of users at once. Some features, like transparency and user control, have even been going backwards. We’ve already spent plenty of time on the issues with Windows Update, and our suggestions for what Microsoft needs to do to fix it, but what’s been missing is a deeper dive into why it hasn’t.
It’s easy to blame the problems with Update on the massive variety of hardware, and decades of legacy software, that Microsoft feels compelled to support in Windows. There is certainly truth to that. But it doesn’t explain blindly pushing Windows 10 on people, or Microsoft’s retreat from user control, which has resulted in more hung systems and boot loops. It also doesn’t explain why even Microsoft’s own Surface products can get into boot loops trying to install updates. One former Microsoft Windows executive I spoke with, who prefers to remain anonymous, believes Update was actually in pretty good shape a decade ago — complete with legacy support — but that cultural and economic issues have caused it to backslide since. His conclusion is that if the cultural issues are addressed, the legacy support problems can be overcome.
Software compatibility is also a major challenge for each new version of Windows, with documented and undocumented interfaces going back decades, and countless applications needing to continue to run. However, for Update specifically, handling legacy hardware and drivers seems to be the more difficult challenge.
Everyone in the industry, whether they used to work at Microsoft or not, almost always includes arrogance among their top reasons for the problems with Update. Having gone forward with a “Microsoft knows best” strategy, the company has used the claim that everyone needs security patches as a shield against criticism of its changes to Windows Update, including its increased use of forced updates. Unfortunately, those updates don’t just fix security issues.
