But Microsoft offered an Extended Security Updates program that moves the true expiration to October 12, 2027. With the deadline growing closer, 10 is conventionally considered less and less safe, and the Windows 11 upgrade is free, so why would someone be holding off? For starters, Windows 11 is a broken mess, and Microsoft absolutely knows it. You can find ways around this, but those methods don't always work, especially after big Windows 11 updates. While many users are holding off on the update, the numbers have gone down from when Microsoft originally discontinued Windows 10 support.