Microsoft Admits Overly Aggressive Windows 10 Upgrade Campaign Was ‘Pretty Painful’ And Obnoxious

Microsoft does not always do things the right way, few people would argue otherwise. However, Microsoft has traditionally been good at admitting when it drops the ball or otherwise could have done a better job. Such is the case with Windows 10 and the super aggressive approach Microsoft took to getting users to upgrade. It was annoying and at times even obnoxious, and while Microsoft can't go back in time and change that, it can at least give users the satisfaction of recognizing it. That's what Microsoft's chief marketing officer Chris Capossela did during a recent video podcast.

One "pretty painful" incident Capossela pointed out was when Microsoft rolled out an update that disabled the red "X" that would normally close the Windows 10 upgrade dialog box. After the update, clicking the red X had no effect. As a result, users who had thought they cancelled the update process to Windows 10 that Microsoft was pushing would wake up to a machine that had upgraded overnight.


"We know we want people to be running Windows 10 from a security perspective, but finding the right balance where you’re not stepping over the line of being too aggressive is something we tried and for a lot of the year I think we got it right, but there was one particular moment in particular where, you know, the red X in the dialog box which typically means you cancel didn’t mean cancel," Capossela admitted.

"And within a couple of hours of that hitting the world, with the listening systems we have we knew that we had gone too far and then, of course, it takes some time to roll out the update that changes that behavior. And those two weeks were pretty painful and clearly a low light for us. We learned a lot from it obviously," Capossela continued.

Microsoft's mea culpa through its CMO doesn't change the fact that some users were severely inconvenienced and pretty ticked off. However, when bad decisions are made, the next best thing you can hope for is that a company acknowledges it, learns from it, and does not repeat it. You can check one of those off in this case, though whether Microsoft learned from its mistake and refrains from repeating it remains to be seen.

For some folk, taking Microsoft at its word will not be easy. The red X situation was not the only time Microsoft was too aggressive in pushing Windows 10. Prior to that, Microsoft silently pushed out Windows 10 downloads to machines in anticipation of users wanting to upgrade. The problem there is that it was taking up valuable disk space, especially for users who were running a fairly low capacity SSD as their primary drive.

While the barrage of nag screens and dubious behavior could have blown up in Microsoft's face, it hasn't. At present, Windows 10 holds a nearly 24 percent share of the desktop operating system market, according to Net Applications. It still has a long way to go before it catches Windows 7, which has a 47.17 percent share, but it has more than doubled the share that belongs to Windows 8/8.1 (around 10 percent).