Is Windows 10 an Impending Disaster for Microsoft?

charlie-brownAs part of Microsoft’s Windows Insider Program, I’ve been testing the pre-release versions of Windows 10 for the last couple of months. I must say that for a Windows operating system, Windows 10 is actually pretty good. It’s no Mac OS X, but Microsoft seems to have learned its lesson from the Windows 8 debacle and has returned to a more traditional “start menu” interface, all while delivering some under-the-hood changes that should please the most techie among us. However, for as decent of an operating system Windows 10 may turn out to be, the way that Microsoft is delivering the upgrade may end up being an unmitigated disaster.

There are two worlds when it comes to Microsoft products. The ideal world where every Microsoft product works exactly as it should in perfect harmony with the hardware it runs on and the users who use it. And then there is the real world. I live in the real world every day. The real world where a variety of factors cause technology products to not work exactly as expected. Microsoft software is especially susceptible to a variety of issues. The plethora of hardware platforms that Windows runs on combined with the sheer number of PCs that have Windows installed virtually guarantee that large swaths of computing scenarios can not be thoroughly tested. In addition, the rampant spread of malware on Windows causes many unexpected problems. So it is almost impossible that a major operating system upgrade like Windows 10 will be glitch-free when released. This is par for the course when referencing a Microsoft Windows upgrade and normally it isn’t a disaster for Microsoft (save, for Windows Vista). The reality is that very few people have historically upgraded their Windows operating systems so the potential for widespread problems has been contained. However, this time is very different. Microsoft is giving away free upgrades of Windows 10 to users of Windows 7 and Windows 8 and making it available as a download through the Windows Update system.

The potential disaster in-waiting for Microsoft begins when millions of possibly unsuspecting Windows users launch a Windows update and end up installing Windows 10 without knowing what they are getting themselves into. The worst-case scenario is that millions of Windows computers become inoperable because the upgrade failed. Any number of reasons may be to blame such as malware, aging hardware, disk corruption, outdated drivers, or just unexplainable Windows “glitches.” Imagine for a moment that starting on July 29th, millions of Windows users suddenly can not use their computers. The tidal wave of support calls and complaints would be enough to bring any company to its knees, but even worse, the ensuing PR nightmare would be a bloodbath for Microsoft. A bloodbath that would likely go on for months and the stigma associated would linger for years.

But shouldn’t the lengthy testing phase with the Windows Insider Program have rooted out these problems already? Even with all the testing taking place, it is highly unlikely that the number of people participating is a fraction of a percent of the installed base of Windows users. Beyond that, the possible fatal flaw is that for all the testing done, it is doubtful that the upgrade process was tested as thoroughly as truly necessary for a rollout of this magnitude. I can’t imagine that many of the Windows Insider participants spent a lot of time backing up their old operating systems, upgrading to Windows 10, wiping it out, restoring their old operating systems, and upgrading to Windows 10 again. That’s really boring and time consuming stuff. So Microsoft is about to unleash an unprecedented (for Microsoft) major operating system upgrade to millions of real-world systems with a relatively minimal amount of testing. I’m sure there are many people at Microsoft who will have their fingers crossed on July 29th.

Even if the worst-case scenario doesn’t materialize, there are still possible PR nightmare storylines for Microsoft waiting in the wings. First, if even a small percentage of people have problems it could be blown out of proportion. Haters gonna hate and just a few incidents of bricked PCs might be enough to cause a “-gate” named uproar. Second, even if by some miracle there are relatively few technical glitches with the millions of Windows 10 upgrades that will take place starting on July 29th, many users may still be bewildered by the sudden change in appearance of their operating system. I know as well as anyone just how fickle computer users can be by the slightest change in their daily computing routines. Windows 10 is a big enough change from either Windows 7 or Windows 8 to make many users flip their lids. While Microsoft may have learned that Windows 8 was too big of a shift for most Windows users, it doesn’t appear they have learned that most Windows users don’t like any change, especially when that change in completely unexpected. It won’t take too many public complaints for this to turn into a snowball of bad PR for Microsoft.

Again, the danger is in the way Microsoft is positioning the Windows 10 upgrade to Windows 7 and Windows 8 users. By putting it out in the user’s faces so prominently, I believe many users will inadvertently start the upgrade to Windows 10 without being fully cognizant of what they are doing. Microsoft makes it seem like upgrading to Windows 10 will simply be just another Windows update, and of course, we’ve all been repeatedly told that everyone should stay up to date! But the reality is that upgrading an operating system is not something you should go into with blinders on. Those who purposely upgrade to Windows 10 at least know the risks and possible consequences of a major operating system upgrade and are expecting the changes. But your mom probably doesn’t. And guess who she’s going to call when her icons don’t look the same as they did yesterday.

As a technology professional who will likely be inundated with calls if any of these nightmare scenarios takes place, I honestly hope this is not as big of a disaster as it possibly could be. I do not wish bad things to happen to anyone’s technology but as I’ve shown, the right circumstances are in place for an upcoming Win-pocalypse. It would be irresponsible for me not to share this information.

Did you ever have the feeling of impending doom? I sure do. Do you think July 29th will be a day that will live in infamy or am I over-thinking things?