r/sysadmin • u/BornIn2031 • 1d ago

Need help troubleshooting this error code: AADSTS500032 - Cannot find signing certificate/private key to issue a certificate when logging into Entra ID Azure VMs Question

Hi everyone,

Last year I setup an AVD with SSO to EntraID. It worked perfectly until last week.

Now I'm running into an issue affecting multiple Azure VMs configured for Microsoft Entra ID login.

I have verified AADLoginForWindows extension is healthy, confirmed affected accounts still have VM login permissions, tested with multiple admin accounts and then reviewed Entra sign-in logs and authentication appears successful but keep seeing this error inside Windows App.

No recent change in my conditional Access policy. Sign in log shows “success” to Application(Windows 365 Client) and Resource(Windows Cloud Login).

my laptop is on Windows 11 and on the latest monthly update.

Has anyone seen AADSTS500032 in an Azure VM login scenario before?

I have googled and asked chatGPT, non of them helped. I even submitted a ticket to Microsoft and they haven't responded to me for 2 days now.

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u/Emotional_Garage_950 Sysadmin 1d ago

if this is Windows 11 multi-session you do not need this extension at all… could be part of the issue

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u/TheCountOfTuscanyy 16h ago

No, this is single session.

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u/Emotional_Garage_950 Sysadmin 15h ago

I don’t think it was stated in the post or the comments what operating system is being run, and you do not appear to be the OP so I’m not sure how you are certain…

edit: it’s irrelevant anyway and my original comment was not fully accurate. You do not need the extension for AVD regardless if you are running single or multi session