After a year of using Windows Server 2025, I'm finally throwing in the towel
Posted by sarosan@reddit | sysadmin | View on Reddit | 49 comments
There is something fundamentally wrong with Windows Server 2025.
TLDR: Listen to the seasoned admins here: don't install Server 2025. Just don't. It's still not ready for prime time, and it probably won't be for another year. Since its 2024-11-01 release, the OS keeps getting worse. You'd think most issues would have been ironed out by now, but nope.
It has been exactly a year (2025-05-28) of using Windows Server 2025 in my environment, and I'm finally accepting defeat by downgrading most of my VMs back to Server 2022.
I used to think the issues reported by others on here were never going to happen to me and that these were isolated incidents. Yes, I've previously said that my environment had no issues (which was true at the time). I just didn't give the pot enough time to boil.
Over time, the issues piled up, and shit just got crazier:
- Installing Server 2025 with a
autounattend.xmlcontaining a disk partition configuration (using the built-in commands) didn't work. Workaround was to use scripteddiskpartcommands created by the generator. - Windows 10 (22H2) and 11 (23H2) workstations kept losing domain trust with a pair of 2025 DCs in place. Fine, let's roll out the Windows 11 24H2 upgrade to fix it. I thought this was all behind us until the issues resurfaced yet again 3-4 months ago, even with 24H2. A few users are suggesting upgrading to 25H2 to mitigate this issue.
- Many servers do not automatically reboot after installing updates, requiring manual intervention. Applying the registry keys in the linked thread seems to have helped.
- The RDS Connection Broker randomly stops working and requires a restart, usually after a Patch Tuesday reboot.
- NVIDIA vGPU on RDS 2025 is broken. Reconnecting to an existing session with a vGPU fails and locks up the server. Since July 2025, the workaround was to remove the GPU from the guest. Testing the exact same setup on Server 2022 works.
- Windows Update has significantly slowed down to a crawl. Reboots take an abnormally long time. My small handful of 2019 VMs are insanely quick to update to this day.
- The WSUS Reporting Service randomly stops working and requires a restart.
- A few days ago, I had a 2025 RDS Session Host server lose trust with the domain.
- Domain replication traffic randomly stops working every few weeks (which explain the trust issues I had above) requiring frequent restarts.
- The final nail in the coffin was when I tried resetting a user's password on Monday, only to realize DC #2 was yet again out of sync.
Yesterday, I replaced that faulty 2025 DC with 2022, and I plan to do the other one today.
Every single server that experienced an issue was a newly created VM with a fresh installation of 2025 (no in-place upgrades). The pair of DCs I setup were only running ADDS and nothing else. There were no time synchronization issues in my domain (DCs pulls time via a pair of firewalls) and DNS did not seem to be the issue at play. The only way to fix AD synchronization was to restart the affected VM.
The rest of my environment will be downgraded within the next few weeks. A few things will remain on 2025 (NPS, DHCP, CA, DFS, SMB... unless they blow up too) but most will go back to 2022, namely AD, RDS and ERP-specific VMs.
What a colossal waste of time.
cjcox4@reddit
We too find 2025 to be gross. And MS doesn't seem to be interested in fixing its issues. Pain in a half.
sole-it@reddit
There is an article telling you the internal stories of Azure and what a hot pile of mess it is even though it's MS's biggest selling point. I wouldn't be surprise WinServer team is the same given they layoffed the whole QA department more than a decade ago and the heavy push on vibe coding (with subpar agent) throughout the MS.
Key-Brilliant9376@reddit
Because it's probably being developed by a bunch of office secretaries using Copilot.
cjcox4@reddit
Actually, I think Microsoft is getting AI in on it to "fix it" because they don't know how to.
The-Old-Schooler@reddit
Rule of thumb I've always heard, and gone by, with Windows server releases is to be one version behind for stability. Let someone else be the guinea pig.
glabel35@reddit
2022 was always been solid for me. So was 2019. Granted I didn’t have the most complex installs.
Darkk_Knight@reddit
Server 2019 is my favorite version. This is coming from an Linux admin guy.
Shanga_Ubone@reddit
What no love for Windows Server 2008?
Anyone?
purplemonkeymad@reddit
Unless it was R2, absolutely not.
sole-it@reddit
definitely a huge step up from 2016 which takes forever to apply one single update.
Big3Poseidon@reddit
Until you have to fight MS teams on and RDS instance.
BanAssaultGeese@reddit
This is the way.
MightyDevOps@reddit
It's with everything in life
eyeheartgilfs@reddit
At this point, I'm starting to assume by default that massive drops in software quality are the result of vibe coding/AI slop. Which is especially easy to imagine coming from Microsoft, given that they're drinking their own Kool Aid these days.
HeresyReminder@reddit
In your opinion, what is the best server environment to work with? I am fairly new and just looking for a little insight into which ones seasoned folks use so I can see the comparison a bit more clearly.
DeerOnARoof@reddit
'19 and '22 are both very stable and still very modern. You'll even find shops operating on 2012 and 2016
ipreferanothername@reddit
im in health IT. 2022 is solid, weve got over 300 and are not having issues.
hilariously we are starting to see vendors say they support OS 2025 - my ass. healthcare software vendors are the worst. im not trusting any of those clowns.
Bad_Mechanic@reddit
2019 has been good to us, and I don't hear many complaints about 2022.
RevolutionaryElk7446@reddit
They each have pros and cons. This is just about Windows Server 2025. Windows Server 2022 is still operating well, but 2025 is cruising alongside the vibe coding push, so it appears releases from everyone have gone down hill lately, Microsoft isn't alone in this.
Rough_Section_3730@reddit
My environment is server 2019 and server 2022. I don’t have any DC’s in my environment, those are managed by another group. My WSUS is on 2022 and all new servers are stood up on 2022.
Doso777@reddit
We have a couple of Windows Server 2025 in production and didn't have any issues with it. YMMV i guess.
largos7289@reddit
Ok hear me out.. MS server tech peaked in 2003 and you will never change my mind. It was the last server that when paired with exchange 2003, had the native backup to do the mailboxes without the need for any other backup software. Since then borked...
zero0n3@reddit
lol but exchange 2003 was garbage. All of on prem exchange was garbage and a PITA to setup at scale (50k mailboxes)
tsittler@reddit
That broken trust relationship bug is a doozy. And the workarounds are “keep a 2022 or older DC”, or “disable machine password resets”. Neither of which are viable long term, imo.
lart2150@reddit
I'm a small deployment but our 2025 domain members have been fine including a terminal server, but we replaced our 2016 dc's with 2022 not 2025. We also use aws AMI's so 1 is not an issue for me. I use the aws SSM patch powershell script so WSUS and the not rebooting issues are not an issue for me.
RevolutionaryElk7446@reddit
Avoid updating your DCs to 2025. The KDC difference between 2022 and 2025 is drastic enough that it causes some migration headaches, including encryption key types getting funky and some machines/users failing trust due to mismatched hashes. They said they fixed it but had to manually reset some machine account passwords that were last reset against a 2016 DC against the 2025s to get em to work.
They tried to 'fix' a lot of things surrounding legacy, and I commend them for that as it's about a decade overdue but a lot ain't going well.
NegotiationTop7253@reddit
People still use Windows Server at all? Thought everyone using Microsoft was suckered into their cloud stuff by now.
ItsMeMulbear@reddit
MicroSlop doesn't care about OnPrem anymore. They want you fully locked into their SaaS platform, paying for eternity.
rswwalker@reddit
We’ve already been paying since the beginning of time, why not till the end of time?
We pay for their SaaS/PaaS/IaaS in fact we’re paying out the aaS!
Lagamorph@reddit
The May update has broken our ability to deploy Windows 2025 from a VM Template, the VMware Customisation Profile can no longer run to set Network and Hostname configurations for some reason. Works fine when rolled back to a template that is configured identically but with only up to the April update.
I'm currently trying everything to work around or resolve it by trying to figure out what I can change in the template build to get it working right again.
Literally nothing else has changed though, same application installs, same hardening policies, only change was a newer Windows update.
Library_IT_guy@reddit
Yep, I had some of the same issues, primarily with RDS and replication. I thought my environment was messed up, but nope - installed 2022 and it's been smooth sailing.
I brought it up here and a bunch of people informed me that I'm a bad sysadmin and smelled bad.
Ok maybe I made up the smelled bad part, but yeah, lot of "your environment is just set up wrong, 2025 is great".
I think 2025 is fine if you're setting up a fresh domain, but migration... yeah, no thanks.
TuxAndrew@reddit
Care to link the post where you brought it up?
bsmovieman@reddit
MS is sabotaging their own on prem offerings to get everyone to move to the cloud.
theAmericanStranger@reddit
As I near retirement, I'm super happy to assist the team migrate to our new web application w/o a trace of Windows components in it. No AD, no servers, and everything is containerized. It's truly amazing how much effort and worries are simply gone; we can 100% concentrate on our application.
No_Resolution_9252@reddit
several of your bullet points are r/shittysysadmin points.
Its been 20 years since RC4 was deprecated. change your god damned krbtgt password already as you should have 40+ times by now. And all the other passwords you haven't changed in that time either.
3 and 4 sound like possible RTFM moments. Cant address 5 or 6 but my dev 2025 boxes have no such problem with updates taking a long time.
thegmanater@reddit
We've had alot of issues with 2025 as well, especially with hyperv and nics. Not a problem on our server 2022 machines with the same configuration. Why do they have to ruin everything for the sake of change...
Ok_SysAdmin@reddit
I have not experienced any of these issues.
Smith6612@reddit
Hey, I had some fun with 2025, too. Storage Spaces is present in three spots, and the only spot that works is the tried and true Server Manager. The rest of the spots break with cryptic errors in the middle of the creation process. The command line doesn't work. Definitely wrestled with that for a good half hour.
Of course if you use the legacy storage pools section, that'll be good until Microslop decides to break it.
Or you can go back to using iSCSI LUNs or shoehorn Networked NVMe. Or Hardware RAID.
discgman@reddit
Yall are running server version above 2020? Holy hell. Moneybags over hear.
RestartRebootRetire@reddit
Obviously the big wigs at Microsoft said, "We shall give them Server 2025, but it will break them and force them onto our Cloud."
3loodhound@reddit
I’ve been running Linux since like 2012, and the last windows server I had to touch for work was also 2012r2 or something like that. The overhead of windows has always been rediculous.
Historical_Score_842@reddit
My rule of thumb is waiting atleast half a year after the last EOL OS is no no longer supported. So that means windows 2016 is EOL starting January, I won’t even entertain 2025 until Q3 and I will deploy 1 test server for atleast a quarter to do testing. Is everyone like this? No I’m sure. But I’ve had trust issues ever since windows vista and 8.
N7Valor@reddit
I'm surprised they haven't squeezed Copilot (malware) running in the background 24/7 on servers yet.
Leather-Arachnid-417@reddit
Dude....please believe me when I tell you this. I been around a long time. NT 4 was more stable than Server 2025. I swear to god.
Key-Brilliant9376@reddit
I'm not sure why anyone ever decides to be a first adopter of new Microsoft operating systems. I won't even think about moving to 2025 until at least the end of 2027. I like to let everyone else find the bugs.
Vivid_Mongoose_8964@reddit
Always N-1 for me unless there is some massive compelling reason...
zeroibis@reddit
When 2028 releases 2025 might be stable.
DDRDiesel@reddit
It's the Vista/7 debacle all over again
pdp10@reddit
We don't use Windows Server for any production, just for testing, but all indications are that we dodged a small bullet by never upgrading past 2022. 2016 really was annoying for updates, like everyone says. 2019 has a RAID driver in the standard ISO that got dropped for 2022, so a few of the bare metal test rigs never got upgraded to 2022, until the last of the elderly test hardware finally gets fully retired so we can re-use the rackspace.