We share a reader’s reasons for not upgrading to Windows 11 and explore whether you have to upgrade at all. TL;DR: Not now, but eventually.
I got an email from a reader. I’m not going to tell you exactly what my correspondent said because, as often happens in reader letters to me, it was rife with unrepeatable words. The least egregious of my Dear Reader’s vocabulary was the opening salvo, which read, «Listen, you idiot, there’s no way I’m upgrading to Windows 11.» On the surface, it might appear that readers like this are unpleasant. But I’ve found that many of my most cranky readers are what can be categorized as » disagreeable givers.» These folks are golden. I find them tremendously valuable. They’re willing to provide feedback that more pleasant folks aren’t willing or able to do. I can’t tell you how many times I’ve posted about something. I got an email back that begins with «listen, you idiot,» followed with detailed and useful information for solving whatever problem I was struggling with. In this case, my correspondent goes on to list the reasons he’s not upgrading to Windows 11. Three of his observations form the foundation of this article. First, Windows 10 will be supported until 2025. Second, some of his current machines won’t run Windows 11 (at least, not without a hack). And third, he believes it’s not worth the retraining time for Windows 11 but is willing to move to Windows 11 when he buys new machines. These are, in fact, reasonably valid points. Let’s discuss the end-of-life issue first. As Ed Bott discusses, Windows 10 will turn into a pumpkin on October 14,2025. The concept of something pumpkining is tied to the fable Cinderella, where Cindy’s fabulous carriage, which her Fairy Godmother magically created from a pumpkin, reverts back to a pumpkin at midnight. In our case, anything that pumpkins changes into a useless or less desirable form at a specific time or date. Windows 10 pumpkins in October 2025 because that’s when Microsoft will stop issuing support updates.
