Hi Jim Perkins
Thanks for the extra detail . The key difference here is how the new Windows App for Mac handles Azure AD credentials compared to the classic RDP client inside Parallels. The “Other user” prompt you’re seeing usually means the app isn’t parsing the AzureAD format correctly. The trick is to use the full UPN with the AzureAD\ prefix, but it has to be typed exactly as AzureAD\yourUPN (so in your case: AzureAD\jim@[Removed PII]..group). If that still fails, try just the UPN (jim@[Removed PII]..group) without the prefix some builds of the app accept one format but not the other
Another thing worth checking is whether the VM has the Azure AD login extension enabled; without that, the Windows App can choke on cloud identities even if RDP works fine. Also, make sure your Mac keychain isn’t caching old creds clearing saved credentials and re‑adding the workspace often fixes this. If you’re still hitting the same error, let me know the exact wording