According to Capossela the exact moment when Microsoft crossed the line was when the red X in the dialog box no longer cancelled the update but instead ran it in the background. He said it was clear fairly soon that they went too far but backpedaling and releasing another update took some time.
Some people said that the update was pushed on to their systems even when they didn't want this. This was painful to hear, said Capossela.
Even though there was a lot of criticism towards the pushy updates, Microsoft knew all along that being aggressive and pushing the envelope is going to be needed in order to get update numbers they were aiming for. Windows 10 was adopted far faster than its recent predecessors.