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.

Legacy hardware is the usual bogeyman

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.

The one word that always comes up is arrogance

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. They sometimes also change features, delete programs, or render a system unusable. Coupled with a lack of information about what is in updates, that qualifies as arrogance.

Hangover from a bygone era?

Much of that “we know better than you” attitude dates from the Ballmer and Sinofsky era. Former Microsoft executive Ben Slivka explained to me that in his mind this “is the same arrogance that led to the arbitrary redesign of the UI in Office 2007 and Windows 8.” As the reins of power were handed over from Ballmer and Sinofsky to Satya Nadella, the New Microsoft was going to be one that did a better job of listening to its users.

And in many ways the company has been. Windows 10 overall is a huge improvement over the direction Windows 8 had taken, and indeed addressed many, if not most, user complaints about the changes from Windows 7. But Update, ironically, has gotten worse. It is now more opaque (hardly any explanation for what an update is or does) and dictatorial (hardly any way to turn off updates, or install them selectively). Because it forces updates — broken or not — onto your system, it can also waste hours repeating a failed effort to install a particular update.

One former Microsoft exec referred to it as a “hangover” from the earlier era. Inside sources say that Microsoft is starting to take the issues with Update seriously at a senior level, but is frustrated that improvements are going slowly. Fortunately, the scope of this issue seems to be finally getting through, as it is rumored that Microsoft will at least allow users to delay updates as part of one of the new Editions of Windows being rolled out this year.

As to why it has taken so long, current and former Microsoft executives I’ve spoken with don’t have a great explanation for this, but my suspicion is that it is driven by the desire to turn Microsoft into a devices-and-services company, without regard for whether its underlying technology is actually up to the task. To that end, Microsoft has been willing to sacrifice the productivity of many consumers and small businesses in the interests of moving things along for the bulk of its users. So it is playing the numbers game, on a large scale. Only the duration and intensity of the backlash seems to have caused it to finally re-evaluate its Update strategy. The latest Insider Preview build allows users to delay some updates and avoid driver installs.

Windows Update is just fine for many who help fund the Windows business

The economics of the Windows business provides another explanation for why Update has evolved the way it has. Every time we write about some issue with Windows Update, we get a ton of reader comments sharing horror stories, and a few who say “what’s all the fuss, we manage our systems, and set IT policies for everything. Works fine.” I think that is a clue to two major reasons Windows Update doesn’t get fixed for everyone else. First, most of Windows’ revenue comes from large enterprises — remember nearly everyone else has gotten it for free and still can — so catering to their needs is the primary goal of the product. Second, Microsoft itself is a heavily managed environment, so employees don’t have to live through the 4am “I’m about to reboot” warning beeps in their hotel room, or the lost work from Auto Updates, or likely even the endless reboot cycle when some updated driver can’t deal with legacy hardware.

So an era of arrogant thinking, a desire to push forward with a new strategy before its technology was ready, and the economics of selling Windows 10 to Enterprises while giving it away free to consumers have all helped create a serious headache around Windows Update. Its planned Creators Edition will provide a good look at whether Microsoft has been able to overcome those hurdles, and address what has become a major pain point for many of its users.

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