r/sysadmin • u/Fatboy40 • Nov 05 '24

Windows 2022 Servers Unexpectedly Upgrading to 2025, Aaaargh! Question

Arriving at work this morning, an "SME" sized business in the UK, something seemed a little off. Further investigation showed that all of our Windows 2022 Servers had either upgraded themselves to 2025 overnight or were about to do so. This obviously came as a shock as we're not at the point to do so for many reasons and the required licensing would not be present.

We manage the updating of clients and servers using the product Heimdal, so I would be surprised if this instigated the update, so our number one concern is why the update occured and how to prevent it.

Is 2025 being pushed out as a simple Windows update to our servers, just like "Patch Tuesday" events, have we missed something we should have set or are we just unlucky?

Is this happening to anyone else?

Edit: A user in a reply has provided some great info, regarding KB5044284, below. Microsoft appear to class this as a "Security Update", however our patch management tool Heimdal classes it internally as an "Upgrade" and also states "Update Name: Windows Server 2025". So, potentially this KB may be miss-classified by Microsoft and / or third-party patch management tools, but it requires further investigation.

Edit 2: Our servers were on the 21H2 build.

Edit 3: Regarding this potential problem your milage may vary depending upon what systems / tools you use to patch / update your Windows servers. Some may potentially not honour the "Classification" from Windows Update, and are applying their own specific classifications, so the 2025 update could potentially get installed even if you don't want it to be.

Edit 4: Be aware that the update to Windows Server 2025 may potential be classified as an "Optional Update" in your RMM, so if you have chosen to also install these then this could also be a route for it to be installed.

Edit 5: Someone from Heimdal has kindly replied on this matter...

... so I thought I'd link to their reply so it's not lost in other comments. So, it appears that Microsoft have screwed up here, and will have cost me and my team a few days of effort to recover. I very much doubt that they'll take any responsibility but I'll go through our primary VAR to see if they can raise this with their Microsoft contacts.

Edit 6: This has made The Register now...

... so is getting some coverage in other media.

It's not been a great week at work, too much time lost on this, and the outcome is that in some instances backups have come into play however Windows Server 2025 licensing will have to be purchased for others. Our primary VAR is not yet selling WS 2025 licensing so the only way to get new 2025 keys is by purchasing 2022 licensing with SA :(

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21

u/ApprehensiveBowl5091 Nov 05 '24

exactly what i've been saying for 20 years.
Every other release of windows is basicly a beta test that we as consumers even pay for, then a year or two after they release a functional OS on the same premise/principle as the "beta"

Examples: Windows 2000/ME = It's a wonder I decided to make IT a career.

Windows XP = Good stuff

Windows Vista = Good lord...

Windows 7 = Good stuff

Windows 8 = ⛥ K̷͎̖̄̎Ǹ̷̹͎̠̌͌͑͘Ḛ̵͛̃͋̌͂E̶͔̰̜̓Ë̶͈͓L̵̯͑ ̸̥̬͕̹́͋B̴̺͖̞̙͐͊̅Ẻ̸̟̠̳̰̒͜F̴̣̪̫̔̋́̚͝Ŏ̵̢͖ͅŘ̸̘̀̋̍̊E̸̗̓̓̊̕ ̶̡̳͉̈́̂̄̕͝M̸͔̗̙͉͑Ȩ̶̗͓̺̺̀ ̶̛͈̎̍͘͝P̴̨̜̺̥͎͂͆Ẹ̵̛̜̗̳̐̓̓̄A̵̞̣͑S̵̙̦͆̇Á̴͓̒̋N̸̻̺̂̐Ţ̵͍̖͛̑͘S̵̹̩̘̮̃͋͌̃!̶͕͈̬̲͊̎̋ ⛥

Windows 10 = Back on track

Windows 11 = lEtS tRy SoMeThInG nEw!?!
Consumers: Are you asking or telling windows 11?
Windows 11 = I have no fecken clue boi!

41

u/baw3000 Nov 05 '24

Windows 2000 was great, possibly even peak Microsoft. Windows ME was a shitshow.

6

u/MeanE Nov 05 '24

I used W2K until some small programs stopped supporting it even before it was EOL. Sad day.

2

u/BlackV Nov 06 '24

ditto, once things started moving to direct x, er.. 8? 10?, then I had to move cause me games stopped working

hmmm actually Am I thinking of 2000 to 7?

3

u/chaoslord Jack of All Trades Nov 05 '24

Friends I knew at the time working on ME called it "the dark time"

1

u/ajicles Nov 05 '24

I was 6 years old when Windows 2000 came out.

3

u/RedShift9 Nov 06 '24

Can you, idk, NOT say those kinds of things? For me 2003 is still 10 years ago.

1

u/ajicles Nov 06 '24

We are closer to 2040 than 2000. 1980 was 44 years ago

1

u/Electric_Ken Nov 06 '24

Exact, back in the days I renamed Windows ME, in French : "Windows Merdique Edition".....

11

u/renegadecanuck Nov 05 '24

The alternating thing does require you to blend 8/8.1 together, and ignore the initial launch of Windows 10.

Windows 10 was a big improvement over 8 and 8.1, but it was still a bit of a tire fire at first. There's a reason so many people held on to Windows 7 until it was ripped away from them (and there's still an entire subreddit of people using it, in affront to all that is secure and righteous).

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u/Old-Olive-4233 Nov 05 '24

XP was also pretty awful until at least SP1 and at the time I'm pretty sure I disliked it until SP2.

1

u/renegadecanuck Nov 05 '24

I also don't remember 2000 being particularly bad, but it also was already end of life when my career started, so my exposure to it has been limited.

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u/BlackV Nov 06 '24

2000 was amazing

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u/BlackV Nov 06 '24

it requires you "ignoring" quite a few things

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u/fish312 Nov 07 '24

What sub

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u/autogyrophilia Nov 05 '24

This feels right but is wrong.

Windows ME was an attempt to modernize 95 with NT components, keeping the system on MS-DOS to try to keep it light. It didn't work well.

2000 (NT 5.0) did. Not without it's issues because it's Windows software.

Windows XP was most of NT 5.0 released to the general public. Built upon 2000, as 2003

Windows Vista (NT 6.0) was poorly handled but it was always going to be painful as it was a huge overhaul with many changes that allow windows graphical session to be pretty secure ( the graphical session, we are still dealing with NTML1, nevermind 3rd party apps...) we are talking features such as the protected screen, running the graphics in user mode and not in kernel mode... As well as improving the support for the modern graphics Put this in perspective. It's what the Unix world is trying to do with Wayland and you see how that is going.

All other versions of Windows build on NT 6.0, with a disappointing lack of additions versus changes. With some of these changes being baffling resulting in Windows 8 in particular

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u/Joe-Cool knows how to doubleclick Nov 06 '24

2000 still only needed up to Service Pack 4 during almost 5 years compared to 6a+post 6a security rollup on NT4.

Windows ME was mostly software/hardware issues though. As an office machine a supported Compaq Armada 1500c had almost zero issues. It would run DOS games worse than Win98 and Windows programs worse than XP. And it would crash with many USB devices. But for just the right combination it'd run well. And faster than XP on that clunker (no EDO + a Celeron 300MHz).

1

u/BlackV Nov 06 '24

ah the old "every 2nd release" fud, glosses over some many details to fit that pattern

1

u/sm9k3y 21d ago

I guess I go back a little further than you, but you've got the general microsoft update cycle mostly...

DOS 5.0 - Amazing!

Windows 3.1 - Well it was GUI

Windows NT - Oh shi!t you made a stable GUI!

Windows 95 - Kinda cool but also WTF, can you keep my computer running for more than 8 hours?

Windows 98 - haha Trolling the newbs (based on 95)

Windows 2k! Sick, a better stable GUI (based on NT)

Windows ME - Oh damn, I actaully feel, bad stop trolling. (based on 98)

Windows XP - Stable GUI got a little better and friendly, I guess we're not trolling anymore. (based on NT)

Windows Vista - I was wrong, how'd you make XP this bad?

Windows 7 - Wait, you could have done this and didn't? I will run this OS forever

Windows 8 - But Tablets and touchscreens? no we don't Give a F***

Windows 10 - The culmination of everything MS has learned, still based on NT and the old menus are there to actually get things done and stable AF for windows

Windows 11 - Don't you want us to make this OS easier by taking away menus/settings you need/know to fix or repair things and moving them around randomly every week? Just trying to make you sysadmins look like morons, AI going to take your job soon anyways