During an interview with Windows Weekly (via ExtremeTech), Microsoft’s CMO Chris Capossela admitted that the company might have initially gone too far. According to Capossela, he said that the reason for the aggressive push was from a security perspective, and that at the start finding the balance was a bit hard.
According to Capossela, “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.”
That being said, the upgrade to Windows 10 is no longer free for users who have failed to take advantage of the offer, so we guess you’ll have to pay actual money to get it now.