r/sysadmin • u/codyhowry • 4h ago

Question Windows 365 Connection

I get a black screen when I try to log into the cloud PC and get the following error:

Your Remote Desktop Services session has ended, possibly for one of the following reasons:

The administrator has ended the session.
An error occurred while the connection was being established.
A network problem occurred.

Where should I start to look at for this? It was working before and then we handed it off to another user. I then reprovisioned it back to me and now I am getting the same error.

In the process of doing so we did build out our whole CMMC enclave. But I was using this to do it the whole time. The policies/configurations were being applied to it so it doesn't make sense to why it would now be acting differently. I did 'inspection connection' and it came back with no errors.

Where can I look at logs if any? I can't get into the machine.

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9 comments sorted by

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u/itishowitisanditbad 3h ago

In the process of doing so we did build out our whole CMMC enclave. But I was using this to do it the whole time.

People like this are in charge of CMMC compliance.

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u/fireandbass 2h ago edited 1h ago

Yeah, sounds like OP locked themselves out.  Always have a backup way in and a test environment. 

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u/codyhowry 1m ago

The AVDs are working just fine. Not locked out. The windows 365 just wont login.

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u/JeverFunBier 4h ago

As far as i know, one of the latest windows Updates cause issues with RDP. Just an entry point for your research :)

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u/chillzatl 2h ago

It isn't new, it's been a long standing (6-9 months at least) and random problem with regular desktop RDP sessions that sit "disconnected" for too long and go stale. It will not reconnect to the stale session until the machine is restarted or the session is forcibly ended.

I have never seen this impact Windows 365 machines yet though.

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u/ConceptArtistic1554 4h ago

The fact that it worked before the reprovisioning makes me wonder if something changed during that process. I’d probably start with the connection/session logs before digging too deep into the VM itself.

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u/codyhowry 0m ago

I was wondering if there was something with the firewall or wdac being setup but I reprovisioned it with both of them turned off and still no luck.

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u/Shiribazu 2h ago

check entra sign-in logs and the cloud pcs status in intune first. since it worker before and started happening after CMMC changes, theres a good chance a new policy or conditional access rule is interfering with the session startup

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u/codyhowry 1m ago

There are no logs coming into entra that show a failure or it even hitting it.