I cannot connect to our VM from my Mac

Good day Jim Perkins

I think you can connect via RDP inside Parallels but not through the new Windows App for Mac tells me the VM itself is fine the hiccup is more likely on the client side. A couple of things to check: make sure you’re running the latest version of the Windows App (they’ve been pushing frequent updates), and double‑check that the AIMS1 VM is added using the correct workspace or subscription context. Sometimes the app caches old credentials, so signing out and back in can clear that up

Also, confirm that the Mac firewall or any VPN you’re running isn’t blocking the connection the Windows App uses slightly different ports than the classic RDP client. If all else fails, try removing the VM entry from the app and re‑adding it fresh; that usually resets the handshake. If you’re still stuck after that, let me know the exact error message you’re seeing and we can dig deeper.

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Additional information -- I have installed the Mac Windows app (11.3.5, which appears to be the latest build) and connected to the VM using a local machine account, but I am unable to do so using my AzureAD account. When trying, I get to a login prompt for Other user and an error message "The user name or password is incorrect." I have tried using AzureAD\jim@[Removed PII].group and jim@[Removed PII].group, and neither works.

However, I have no problem connecting from my Parallels VM via RDP using both the local machine account and the Azure AD account. Further, I can see that jim@*[Removed PII].*group is identified as an Administrator, so this account is authenticated on our VM.

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

I was just trying to log in again from RDP in my Parallels VM and discovered the following -- if I try to log in using jim@*[Removed PII].group or AzureAD\jim@[Removed PII].group and use my just-changed password (I verified that the new password works by logging into portal.office.com and portal.azure.com), but it will not work. But my PIN does work. When I try to log in using AzureAD\jim@[Removed PII].group of jim@[Removed PII].*group from the Mac Windows app I get a "this log in method is not allowed contact your admin" error message. I believe I have everything enabled on the VM to enable RDP access otherwise I couldn't log in from my Parallels VM using RDP.

But why can I log in using my PIN but not my newly changed password?

We have already rebuilt the VM for the second time to fix this problem and have been unable to get beyond this basic authentication problem to start deploying our app.

This is actually a common quirk when mixing Azure AD logins with RDP. What’s happening is that PIN sign‑in is backed by Windows Hello, which uses a local credential provider tied to your device, not the raw password. That’s why the PIN works but the new password doesn’t. The Windows App for Mac, on the other hand, doesn’t support Windows Hello it only tries to pass through the password credential, and if the VM isn’t fully configured with the Azure AD login extension or the right policy settings, you’ll hit the “this login method is not allowed” error.

• Make sure the Azure AD login extension is installed and active on the VM. Without it, password‑based Azure AD sign‑ins can fail even if RDP inside Parallels works.
• Verify that the VM’s Network Level Authentication (NLA) is enabled and that the Azure AD account is allowed for RDP under local security policy.
• Clear any cached credentials in the Windows App for Mac and re‑add the workspace fresh.
• If you’re still blocked, try logging in with the local account first, then switch to Azure AD once inside that can sometimes bypass the credential provider mismatch.

Bottom line: the PIN works because it’s local, the password fails because the app isn’t negotiating Azure AD auth correctly. Getting the extension and policies aligned should fix it.