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.
The Windows pumpkin date
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. Unfortunately, since millions of machines can't be updated to Windows 11, Bott rightly contends that all those machines will then become security nightmares.
But 2025 is almost four years away, which means if you want to use your Windows 10 machine until support ends, nothing is stopping you.
No Windows 11 for you
It's not like we haven't mentioned this before a lot. But Windows 11 won't run on all PCs. Only certain processors will be supported, only 64-bit machines will be supported, and only machines with a TPM chip will run Windows 11. For the very latest, keep an eye on Ed's article on the subject, which he keeps up to date.
If your machine isn't supported for Windows 11, you can certainly keep using it with Windows 10. We don't recommend using it after updates end, but that's years away. Cross that bridge when the pumpkin pops.
You could do another thing, which we do not recommend, is install Windows 11 by hacking your PC. My Internet Press Guild colleague Avram Piltch has a helpful guide if you want to take that route. But be forewarned: you lose most of the added security goodness Windows 11 offers if you do.
Retraining for Windows 11
Here, I mostly disagree with my disagreeable giver reader.
Let's be clear. If you know how to use Windows 10, you don't have to be a rocket scientist to learn to use Windows 11. So the Start icon is in the middle of the screen. Big deal. You can actually move it back, if you want to, with a simple tweak.
So he can cry all he wants about retraining. It honestly ain't no big thing. Get over it.
But you don't have to update to Windows 11
In general, operating systems need to be upgraded regularly. Hardware evolves. So do threats. There comes a time when the overall architecture of an ageing OS begins to weigh down with legacy elements, making it harder to add innovations. Upgrading an OS allows vendors to make big-step changes that incorporate new innovations and new protections.
Vendors also like new operating systems because they give machines that new PC smell. There's usually a bump in PC sales when a new major release comes out, so vendors like to see new OS versions every few years. It allows them to add some of those new features we discussed but also market using a differentiator that says their older systems are older and that their newest products are the new hotness.
As for security, I asked Ed how to characterize Windows 11 vs. Windows 10. He told me:
I personally don't think it's helpful to make blanket statements like "Windows 11 is more secure than Windows 10." Better to simply say, if your hardware supports Windows 11, and there are no critical features that you would lose, then you should upgrade. It's a platform that's being actively developed. Windows 10 is a legacy platform.
But here's the thing. Windows 10 can be secure, especially if you update as Microsoft recommends.
It's only February of 2022. October of 2025 is 43 months away. A 2018 Microsoft study states that the "optimal age of PCs is no more than four years old." Even if you buy a new Windows 10 machine right now, it's still going to have most of its usable life while it's within the optimal age window.
Of course, at some point, you will have to upgrade. Yes, some OSs are safe to use, even if they're 40 years old. Game of Thrones (technically, A Song of Ice and Fire) author George R.R. Martin writes using WordStar 4.0 on DOS. But DOS is safe because it's pre-Internet. It's so old that while malware did exist back in DOS's dark days, it didn't send your personal identifying information to criminals.
But the fact is, if you're running an Internet-connected OS (and you are, because how could you survive otherwise?), then you'll need to upgrade at some point. Once Windows 10 loses support updates, hackers will be free to flood the Internet with unchecked exploits, and everyone running Windows 10 will be at risk.
But that's not for 43 months. So, if you don't want to upgrade to Windows 11 today, don't sweat it. Just put it on your calendar for the early fall of 2025.
What's your Windows story? Are you running Windows 10? Windows 11? A mix of both? Let us know your thoughts and plans in the comments below. Feel free to post something disagreeable and useful (but not mean or disgusting, please). I always welcome learning new things.
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