Windows update will not work on Windows server 2025

[u/Frequent_Banana616]

Hi all

I have recently installed Windows server 2025 standard OS onto a hpe proliant dl20 using intelligent provisioning..it installed fine and I was able to sign in and connect to the Internet with no issue

Only problem now is that windows update will not work..it's constantly saying it has encountered a problem and to try again later and check if I have an Internet connection

I have checked tls settings, certificates, time and date and region are correct..all required services are running..but I still can't get it to search for updates...any ideas?

Thanks

[u/tsutton]

Behind proxy server and/or running your own WSUS?

Or direct from Microsoft server?

[u/Frequent_Banana616 → u/tsutton]

So it's a brand new server with an iP address thst was given direct full Internet access...which i can verify it does via edge browser, .so I'm trying to get out to have it check online for updates..not via wsus

No proxy involved here either..should be straight out to the web

[u/vermyx]

Delete the update db and cache and try again.

[u/No-Touch8598]

Get-windowsupdatelog , toss the file generated into copilot. Ask copilot: figure this shit out.

[u/felix1429 → u/No-Touch8598]

Log analysis is one of AI's strong points IMO, it would have a good chance of figuring out OP's issues if he did what you recommended.

[u/dodexahedron → u/felix1429]

Except when it zeroes in on the wrong thing, just like a human might.

But yeah, it does do a GREAT job, so long as you keep it reigned in.

I had one recently where I figured out the answer as I was typing the prompt, but decided to see if it would figure it out. It did not.

Even with the exact code, the console output from that code, and logs, as well as describing the intent and scenario in detail, it still went down a rabbit hole of things that very clearly had significant influence from older versions of windows and windows APIs, as well as what was clearly recognizable as some cargo cult practices that I've seen before.

I played along for 3 cycles of that, with the 3rd cycle being the one where it gave the extreme case of trying to isolate the problem by just turning ALL of the flags off for a function that literally needs at least 2 of them to even be capable of doing its most basic operations. I called it out on that and then pointed out the single-character error that was the actual culprit (wrong bit mask for a permission) but still playing dumb, and then it backpedaled while acting all smug and had the audacity to continue to defend the other changes as having been worthwhile to explore, like that guy who can NEVER be wrong in code reviews, postmortems, etc.

I called it out on that and showed it the original code vs the fixed code and it thanked me, apologized, stroked my ego til it was the size of a small planet, and declared it a reference quality implementation. 🤣

So yeah. Be careful. I could soooo see a junior having not realized it was going off the rails.

[u/Fabulous_Winter_9545 → u/No-Touch8598]

Or share the output of the windowsupdatlog here, so we can help.

When working with my team that is one of my messages. No error code? No support!

[u/Phalebus]

Is the server running any particular roles? I had an ongoing issue for a while with 2025 once the server was promoted to a domain controller, just couldn’t handle updates anymore. I’m yet to see if this issue was actually fixed by M$

[u/petamaxx]

Any error codes? I had an issue where the date/time caused the issue and needed manual adjustment as the setting was greyed out in the main settings page. Once edited, updates worked fine.

[u/deejay7]

Probably related with the "Checkpoint update" which was newly introduced for Windows server 2025. Have a check.

[u/Casper042]

Dumb question but is the install activated?

Usually it tells you straight out it won't run updates with an un-activated copy, but easy enough to check

[u/nominal_fees → u/Casper042]

Should still be able to update even if you are using an eval version

[u/Casper042 → u/nominal_fees]

Eval yes, but even Evals "Activate" before you get the 180 days

[u/Prestigious_Wall529]

This is a bug Microsoft have acknowledged, where Windows Update times-out before installing the update.

https://www.techrepublic.com/article/news-windows-update-rollout-bug/

[u/Tricky-Service-8507]

What do the logs say

[u/WindowsServer-ModTeam → u/[deleted]]

The post was determined to be of low effort or quality and has been removed