Should I Update to Windows 11? (May 2025 update) (2025)

A definite maybe.

The end-of-support date for Windows 10 is getting closer. Do you need to upgrade to Windows 11?

Applies to Windows: 11, 10

Updated April/May 2025.

As the countdown to Windows 10’s end of support approaches, my answer has shifted. Up until now, there hasn’t been a compelling need to upgrade. While that hasn’t really changed, with the October 2025 deadline getting closer, it’s time to consider what you want to do.

I’m not saying you have to

Before anyone takes this the wrong way, I am in no way saying you must upgrade to Windows 11. I’m going to recommend that you do so if you can, but that’s all it is: my recommendation.

As I’ve said in multiple places and times, Windows 10 will keep working beyond its end-of-support date. You can continue to use Windows 10 safely by taking more responsibility for your security. Eventually (though not immediately), some of your third-party applications may also end their support for Windows 10.

If you don’t want or can’t upgrade to Windows 11, keep calm and carry on in Windows 10.

Windows 11

Windows 11, now approaching four years old, is a fine version of Windows.

I’ve been using it daily almost since the day it was released, and I’ve been happy with it from the start. I have it on both my primary desktop PC and my laptop.

Honestly, it feels more like a large feature update to Windows 10 than a completely different version of Windows. The taskbar was moved and there’s a somewhat different look and feel to it, but it’s pretty much the same operating system. I know not everyone feels this way, but from my perspective, there wasn’t much to get used to when I switched. It, and I, just kept on working.

Until now, though, my take was that Windows 11 rated a big “meh”. There wasn’t any compelling reason to switch.

However, since Windows 10’s end of support is getting closer, I think it’s time to consider the change — as long as your hardware supports it.

Yes, the requirements are frustrating

One frustrating aspect of Windows 11 is its system requirements. Many machines — even some newer ones — fail the compatibility test.

There are workarounds for installing Windows 11 if your machine isn’t up to the requirements.

(Microsoft has disabled many of the previous workarounds, and it’s possible that mentioned in the article above will be disabled as well at some point. Microsoft has also indicated that machines updated to Windows 11 bypassing the hardware requirements may not receive updates or may have other issues Microsoft won’t address.)

Windows 11 on a new machine?

New machines are likely to have Windows 11 pre-installed.

Keep it. It’s fine.

There’s no reason to run away from Windows 11. As I said, I use it every day, and it’s just as fine as Windows 10.

Aside: The every-other-version “curse”

This is not a reason to avoid Windows 11, but some may take it as one. It’s at least interesting.

It’s as much superstition as anything else, and by itself it’s not a reason to avoid anything, particularly since there’s been no word about any successor to Windows 11.

And yet. There does seem to be a pattern.

Make of it what you will.

But what about… ???!!!

To say Windows 11 elicits strong opinions in some people is perhaps an understatement. I want to address some of the more common ones.

Everyone hates Windows 11!

No. Just no. In fact, a lot of people like it. Here’s the thing: you’re only likely to hear from those experiencing issues. They look for help (or just vent) in various public forums. The people who like it — the people for whom it’s working just fine — are just quietly getting on with their work. I’m convinced there are many, many more of them than there are haters.

Microsoft is evil/spying/scanning/etc!

That’s not a Windows 11 problem. I know some feel Windows 11 is somehow worse in some “Microsoft is evil” kind of way, but I don’t see it. Windows 10 introduced many of the telemetry things people complain about. To the best of my knowledge, Windows 11 hasn’t made that significantly worse.

Windows 11 pushes things on me I don’t want!

That’s not a Windows 11 problem either. Seriously, every version of Windows includes features and functionality that many (though, again, not all) people object to. Sometimes people grow to like the features, and sometimes the features disappear.1

In addition, many of the current complaints aren’t about Windows 11 per se but about specific features being introduced and pushed hard across both Windows 10 and 11. It’s Microsoft pushing the features that is worthy of your ire. (*cough* OneDrive *cough*)

Microsoft is colluding with hardware manufacturers to force us to buy new machines!

Oh, hell no. Honestly, this conspiracy theory frustrates me to no end. No one is forcing you to purchase a new machine. Stick with Windows 10. Switch to Linux. Use one of the hardware requirement bypasses. None of those options require you to spend a dollar2.

Yes, eventually you’re likely to get a new machine, not because anyone forces you to, but because it’s time. That’s been the case since PCs were invented. As a side effect, you’ll have a machine that meets the new hardware requirements.

You’re just a Microsoft shill!

I often get accused of being on Microsoft’s payroll (I haven’t been for decades), getting paid to endorse them (I have yet to see a check), or some kind of Microsoft apologist. When I recommend you consider Windows 11, it triggers the anti-Microsoft crowd something fierce.

I’m a pragmatic realist. I have lots of complaints about Microsoft and Windows. Lots. But I also realize that leaving Microsoft and Windows behind isn’t in the cards for many people, including most of my audience. Railing against all of Microsoft’s evils — of which I agree there are many — wouldn’t be helpful. Helping people switch to something else would benefit only a small portion of my audience.

Instead, I try to help people make informed decisions and work within the system they have.