Microsoft’s over-aggressive push with Windows 10 updates “clearly a lowlight for us”

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Microsoft’s Windows 10 operating system achieved some significant new milestones this year. First of all, the company shipped the Windows 10 Anniversary Update in August, bringing a lot of new features to PCs, phones, Xbox consoles and HoloLens headsets. Then at Ignite 2016 in late September, Microsoft announced that Windows 10 was now running on 400 million devices, though the growth of the operating system has clearly stalled since Microsoft ended its free upgrade offer for Windows 7 and Windows 8 users in July.

While this limited time offer definitely helped Windows 10 become the second most used Windows version after Windows 7, the move also caused some PR nightmares for the company this year. Chris Capossela, Chief Marketing Officer at Microsoft, acknowledged it while he was once again a special guest during this week’s Windows Weekly podcast (via Slashdot).

When asked to share some of Microsoft’s low points in 2016, the exec recalled the moment when a change to the Windows 10 upgrade prompt earlier this year led to users complaining about forced updates. Microsoft eventually delivered a patch after two weeks, but Capossela admitted that the whole episode was “very painful” for the company. Here is his full, unedited quote below (you can watch it on starting at 17’30):

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. 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 lowlight for us. We learned a lot from it obviously.

As a reminder, a Californian woman even sued Microsoft for $10,000 this year over a “forced” Windows 10 upgrade that made her PC unusable, and the Redmond giant lost the trial. Do you agree that Microsoft’s aggressive Windows 10 updates were one of the company’s most disappointing moves this year? Let us know what you think in the comments below.