Windows 11: Upgrade Now or Wait?

alok-scalefusion · 2025-02-20T12:11:10.389Z

October 14, 2025, is approaching fast—the official end of support for Windows 10. Just a few months left, IT admins are facing a critical decision: upgrade to Windows 11 now or stick with Windows 10 for as long as possible?

Many discussions have been circulating on this very topic, and from what we’ve seen, opinions are divided. Some IT admins have made the switch seamlessly, while others are facing challenges related to hardware compatibility, performance, and application support.

One recurring concern we hear from MDM users who are managing Windows devices is the dilemma of when and how to migrate. With a fleet of endpoints to oversee, any transition needs to be smooth, secure, and well-planned.

For those who’ve upgraded – How did the transition go? Any performance or security improvements?
For those holding off – What’s stopping you? Are compatibility concerns, stability, or cost holding you back?

Let’s discuss the pros and cons—are you already making the move, or will you hold onto Windows 10 until the very last moment?

Join the discussion and share your experiences!

Looking for a security comparison? Check out this breakdown: Windows 10 vs. Windows 11 Enterprise Security Comparison

Already upgraded – No issues so far!
Upgraded, but faced some challenges
Still on Windows 10, but planning to upgrade soon
Holding off as long as possible
Not sure yet – Still evaluating

0 voters

ajason · 2025-02-20T12:52:12.929Z

I am in the process still. The PCs that I have already upgraded have not had any issues - the transition went smoothly. The ones that are still on Windows 10 I am planning to get everything upgraded well before the deadline. I did not vote, because I do not fit in any one of the choices and I could not choose more than one.

I have been using Windows 11 for several years now. That experience makes me feel unconcerned about upgrading all our PCs. I know that there are those who feel that Windows 11 is the “every-other” bad OS release. I simply have not seen that. It also feels enough like Windows 10 that most, if not all of, our users have no issues using it.

alok-scalefusion · 2025-02-20T13:51:53.983Z

Thanks for sharing your experience! It’s great to hear that your upgrades have been smooth so far. Since you’ve been using Windows 11 for years, your insights are valuable—especially for those still hesitant about the transition.

You’re right, Windows 11 does feel familiar to Windows 10 in many ways, which helps with user adoption. The “every-other-bad-OS” perception is definitely a hot topic, but firsthand experiences like yours can help clear up concerns.

Would love to hear—are there any specific steps or best practices you followed to ensure a smooth upgrade? That could be really helpful for others planning their migrations!

dbeato · 2025-02-20T14:29:50.611Z

We started to migrate to Windows 11 most of our customers since last year. It does take time and some legacy apps that work on Windows 10 just might not work on Windows 11 from some odd reasons or security reasons. It does give people the incentive to update the applications and systems they use that are stagnant.

PatrickFarrell · 2025-02-20T14:35:37.292Z

I would hope by now everyone is well underway. For those who have not started, you have 237 days.

How many machines do you have to do per day in order to hit the target?

Sean-Spiceworks · 2025-02-20T15:26:35.906Z

PatrickFarrell:

I would hope by now everyone is well underway. For those who have not started, you have 237 days.

At least based on this, while 40% are already on Win11, another 40% is still in the planning stages… Are you taking the leap to Windows 11?

ldobson01 · 2025-02-20T16:53:01.237Z

Currently 90% of our machines are running windows 11 and the last 10% are getting replaced this year. so far i haven’t had many issues regarding specifically the OS but most of my issues come from lack of support from software companies who only make their software available for windows 10 and refuse to make a windows 11 version.

Transition went fairly smoothly after an end user does the update i expect them to call me and most of the time all i need to do is give a quick orientation of the major changes and show them how to get back into their regular workflow with the new OS

You kind of have your hands tied as Windows 10 is EOL in October and if you decide to stay with windows 10 after that you will be slammed with LTS fees

GDaddy · 2025-02-20T17:00:00.474Z

we are Healthcare, we have an App that does not support Win 11, the plan is update it to a supported version in August.

So we will have about a month to roll out 11. Yippeeeee…

Edit: about 600 machines

spiceuser-l31io · 2025-02-20T17:03:04.708Z

The poll doesn’t address those of us that handle multiple business networks.

Some have been upgraded without issue.
Some have had severe issues and had to be reverted back to 10.

And there are a few that will be taking advantage of the Microsoft ESU program.

Phil7965 · 2025-02-20T19:01:55.266Z

IF they have the resources to do so shrug

Phil7965 · 2025-02-20T19:14:54.665Z

We are squeezing every last ounce of Win 10 we can get. I’m in this till the bitter end.

ich-ni-san · 2025-02-20T19:28:15.728Z

If our computers were capable, I’d start the upgrade when I finished typing this response.

somedude2 · 2025-02-20T20:15:44.464Z

Still mixed…have machines that work just fine running win10 but aren’t upgradable,
which is very annoying, and they are obviously not old-and-slow machines…sigh

So…for those…waiting till the last minute, Win11 itself has had it’s weird and strange glitches,
but nothing we couldn’t work around. However we are mostly office apps, and autocad, which
is a potential thing ,we need to do some testing of that at some point (soon), but I don’t forsee issues really.
(famous last words)

BucDan · 2025-02-20T20:20:28.123Z

When you guys upgrade, stick to 23H2 for the time being. It’ll give you less headaches and then you can test 24H2 and roll the update later if all goes well.

kwelch007 · 2025-02-20T20:41:57.443Z

GDaddy:

So we will have about a month to roll out 11. Yippeeeee…

Edit: about 600 machines

Just a suggestion, but if you haven’t already it might be wise to get your deployment mechanism in place. There are a few options (I’ve only used MEM/Intune and Powershell remoting.) Whatever you use it will likely take some time to roll out, and should be tested before D-Day.

GDaddy · 2025-02-20T20:49:57.990Z

to Kwelch, Image is built, tested and ready to go. when we are closer to rolling out the new App, we will start planning deployment. Currently we use MDT, but are testing other options like Smart Deploy. Intune is too spendy for us at this time.

And yep, i am not sure we will get all re-spun before the cutoff date, but we will be close.

alok-scalefusion · 2025-02-21T07:34:30.794Z

That’s a great point! The shift to Windows 11 isn’t just about upgrading the OS—it’s also a chance to modernize applications and systems that may have been running unchanged for years. Legacy compatibility can be tricky, but it’s a good incentive for updates. Have you found any good workarounds for apps that didn’t work initially?

alok-scalefusion · 2025-02-21T07:44:16.204Z

Thanks for sharing your experience! It sounds like you’ve got a solid transition plan in place, and yes, I agree the lack of software support for Windows 11 is definitely a challenge. Also, a good point about the LTS fees, because sticking with Windows 10 post-EOL isn’t a cost-effective option.

alok-scalefusion · 2025-02-21T07:51:33.844Z

That sounds like a tight timeline! Hopefully, the app update goes smoothly because managing 600 machines in just a month is definitely a challenge!

Also, are you planning a phased rollout or an all-at-once deployment? Would love to hear how you’re preparing for it—especially in a healthcare environment where downtime is critical.

fr0thgar · 2025-02-21T08:51:47.553Z

We’re planning on the upgrade in 2025 if all goes according to plan. we have a few PC’s on 11 already and have had no issue with that, but the majority is still on win10. its “only” about 150-200 PC’s but on 4 different locations. I’ve also got some compatebility issues I need a solution for. half our devices are not compatible