Microsoft: Perform in-place upgrades to Windows Server 2025 with one reg key.

Posted by techvet83@reddit | sysadmin | View on Reddit | 68 comments

Microsoft has announced that you can do in-place upgrades to Windows Server 2025 from Windows Server 2019 or Windows Server 2022 just by adding a registry key. No more copying ISO files around or having to mount/dismount them via your favorite cloud console. See Opt-In Windows Server 2025 Feature Update from the WS 2022 and WS 2019 Settings Dialog | Microsoft Community Hub for details. See the "Planning For the Upgrade" section for the usual caveats.

[-]

DestinyForNone@reddit

Who volunteers as tribute?

[-]

Makanly@reddit

I'll do it with our Configmgr servers. I already IPU them from 2012r2 to 2019.

Servers are cattle, not pets. If something goes wrong Slaughter them and replace them.

[-]

ScriptThat@reddit

Meh. Restore a backup to a new VM and try it out. You don't have to test in production.

[-]

wrnkledforskn@reddit

You always test in prod, especially on a Friday afternoon.

[-]

ScriptThat@reddit

What's the saying again..

Everyone has a test environment. Some even have a separate test environment.

[-]

Stonewalled9999@reddit

Yeah this is going to end super well !!!

[-]

PTCruiserGT@reddit

I'd be all over this if it was for 2019 to 2022, but 2025 still has too many issues.

[-]

Stonewalled9999@reddit

Wasn't there an issue last year/2 years ago where MS "accidentally" patched 2022 and upgraded to 2025 and people were in a bind since....licensing?

[-]

OinkyConfidence@reddit

Yes there was! I read about one org that inadvertently upgraded all their servers to 2025 via this erroneous method, then got nagged about not being licensed for it!

[-]

yomammary@reddit

This

[-]

Just_A_Dance@reddit

Must limit it to your DCs to avoid any risk

[-]

MissionSpecialist@reddit

And start with the one that holds all your FSMO roles, because it knows better than to ever misbehavile.

[-]

Professor_SuckMyAss@reddit

I’ll do it lol Just give me access to your server

[-]

willdeleteacct1year@reddit

I am kinda hating my fucking job and career choices lately and my job place has become toxic as fuck not totally against an accidental nukage of their shit.

[-]

Pyrostasis@reddit

gif

nope no thanks

[-]

Wolfram_And_Hart@reddit

If I get time I’ll see if I can spin up a backup and give it a shot.

[-]

gr33nnight@reddit

Just my experience but all our DCs are 2025 and haven’t had any issues.

[-]

GhostlyCrowd@reddit

If you really hate yourself mix 2025 and 2019 dc's ask me I know...

first 90 days and testing were perfect, second 90 days' worth of kerberose onion peeling was awful.

[-]

cosmic_orca@reddit

Whay were the issues you experienced?

[-]

Stonewalled9999@reddit

that is exactly what happened to me. Client had 1 2016DC 2 2025DCs Jan 1. Was fine until....March....then the world blew up

[-]

ledow@reddit

If you start clean on 2025, then they're fine.

Otherwise, SO MANY people have seen problems updating their DC to 2025 by any method and/or even mixing/matching clean 2025 with existing DCs.

Sorry, but I'm barely even caring about a move to 2025 and I've heard nothing but problems with 2025 DC's either, and I'm not sure I've ever actually done a "from-scratch" DC on a clean domain in my entire life, except for prototyping/testing. There's always a DC legacy to bring with you, and the chance to start with a fresh domain entirely on 2025 is beyond almost everyone.

[-]

godspeedfx@reddit

I'm not touching Server 2025 until I stop seeing so many people complain about it, haha. I just in-place upgraded all our 2016 servers straight to 2022 without a single issue. All I see are horror stories from people running 2025.

[-]

aleinss@reddit

2025 is pretty solid, as long as you don't have it as a DC.

[-]

Arkios@reddit

What’s the issue with DCs on 2025? Asking as someone that is about to migrate from 2016/2019 DCs.

[-]

Cormacolinde@reddit

Kerberos screwups, schema incompatibilities, dMSA being a half-baked insecure mess.

If you move ALL your DCs to 2025 you are likely going to be OK, but honestly just stick with 2022.

[-]

finobi@reddit

I built new AD with 2025 and few 2025 member servers, no issues so far. Client devices will be entra joined.

[-]

Stonewalled9999@reddit

greenfield with 24H2 and higher PC clients is fine. Existing behemoths with upgrades have noticed various issues.

[-]

JDS_802@reddit

Can confirm that it was a headache getting the 2025 DC to work correctly. It replaced our 2016 primary DC. The other DCs in our environment are 2022. If I could go back, I would’ve just gone with 2022. I did eventually get things working, but it was way more of a hassle than it should’ve been

[-]

aleinss@reddit

https://www.reddit.com/r/sysadmin/comments/1o4t4nv/psa_do_not_use_windows_server_2025_as_the_schema/ https://www.reddit.com/r/sysadmin/comments/1nhtlx7/server_2025_dc_clients_randomly_unable_to_log_in/

[-]

slm4996@reddit

A DC (unless a new domain) or a terminal server, or a nps server, or a RAC role.

Basically fine for anything that doesn't handle authentication on the server.

[-]

GhostlyCrowd@reddit

our 4 NPS servers are 2025 zero issues, but we stood up two 2025 dc's and let them coexist and that fucked us so hard... it was like peeling an onion trying to fix all the issues they caused just being in the forest with our 2019 dc's

2022 for dc's since forth for us.

[-]

Affectionate-Cat-975@reddit

I never in place. Always a new install

[-]

godspeedfx@reddit

I used to feel this same way (rightfully so) but it's an aging philosophy. It's much safer these days for 2016 and up. I've only had 1 or 2 issues out of 100 and they were easily solved.

[-]

trail-g62Bim@reddit

Yeah I think I am going to try in place. I have done it a few times without issue and getting all of the coordination and $$ for new servers is often a pain for the application servers.

[-]

Sunsparc@reddit

2025 has been pretty great for our non-DC servers. We have some applications running as HA pairs on a mix of 2019/2022 and 2025 servers and they all run remarkably better on the 2025 servers.

[-]

applecorc@reddit

Yep. 2025 servers are running great for us. Don't have any setup as DC though.

[-]

GhostlyCrowd@reddit

Same experience, 2025 DC's cause the big fucking sad tho.

[-]

Gummyrabbit@reddit

I’ve been running about thirty 2025 servers with no issues for about a year. SQL, file servers, IIS and non-Microsoft applications.

[-]

Ok_SysAdmin@reddit

I have about 70 servers of various roles, including my domain controllers running 2025. Zero issues to date. To much fear mongering around here.

[-]

godspeedfx@reddit

Nice! What can I say.. we're a skittish bunch =D

I'll continue holding off for a little while longer. I've never moved to the latest server version and it's served me well thus far.

[-]

Arkios@reddit

Dang it, this is making me second guess moving our 2016 systems to 2025. I was so excited to be done with the horribly slow Windows Updates on 2016.

I coincidentally was just troubleshooting some weird performance issues on a new Server 2025 VM when I opened this and saw this comment. /cry

[-]

godspeedfx@reddit

Servers should be fine to upgrade, but be careful with DCs. 2025 DCs don't play nicely with older DCs in the mix. If you can go all 2025 DCs at once, you'll probably be fine. Just do plenty of research =)

[-]

allworknopizza@reddit

What kind of problems ?

[-]

godspeedfx@reddit

Mainly problems with mixed DCs (2025 + older). If you can cut over to all 2025 DCs at once, you'll probably be fine. I'm not risking it yet personally, but people are doing it without issues.

[-]

thetrivialstuff@reddit

That sounds like a terrible idea. Could be a fun prank to roll out this key with a GPO, though.

[-]

luke1lea@reddit

Insert Anakin/Padme meme here

Not in production though right?

[-]

mnvoronin@reddit

Of course not, testing environment only!

[-]

8BFF4fpThY@reddit

Everyone has a testing environment. Some are just lucky enough to have a separate production environment.

[-]

Stonewalled9999@reddit

my MSP treats my prod like a dev environment if that counts

[-]

jetski_28@reddit

Didn’t MS roll out an update last year that caused in place upgrades of Server OS’s?

[-]

WillVH52@reddit

Correct

[-]

cbiggers@reddit

Good timing, we had a 2019 server we were retiring so I decided to try this out just for fun. Followed the article, added the regkeys, but can't get the update to display. Ohwell.

[-]

RainStormLou@reddit

who the fuck is leading project management at microsoft? they have the worst priorities and it's no wonder entire countries are dropping their shit.

"our users definitely want us to have 19 half baked update paths (including clandestine update paths in the background that we'll pretend are application updates even with core operating system components and especially if you've blocked Microsoft updates) that we're going to forget about within 3 months for sure, push a ton of pretty consistently fucked up server and OS updates, ignore persistent issues that have been plaguing users since 2016, AND we'll keep our Enterprise offerings in a constant user interface wild west with a whole bunch of useless functionality that no systems administrator would ever ask for. don't bother with persistent settings or properly utilizing cookies. we'll just offer the welcome tour every fucking time they log in for five fucking years"

"OH, we also need to make sure none of the development teams can communicate with each other, and then we'll name every fucking thing we have co-pilot so that co-pilot can read co-pilot documentation on co-pilot so that it can be better prepared to code co-pilot. did you guys send that email about the new batch of 10,000 people were laying off this week?"

I might have some feelings

[-]

Haplo12345@reddit

Kick Satya out and let an engineer run the company again.

[-]

DiligentPhotographer@reddit

IMO the M365 web interfaces are not "enterprise" at all. They're just easy mode for non techy people to manage their own shit and then fuck it up just enough so a consultant pulls their hair out lol.

Oh wait, I forgot about the whole change to graph from normal powershell. So now I have to remember 2 sets of commands if I'm working on an on prem or m365 environment.

[-]

NoneOfTheAbove999@reddit

I tried this with a test VM, 2019.

This was supposed to appear after editing the registry. I threw in a bonus reboot.

It did not appear as an option.

[-]