Remote Desktop / Windows App Failed Login

Question

I am receiving this failed login error when trying to add a workspace to Remote Desktop / Windows App:

Certificate validation failed

Try again by doing the following:

1. Close the current browser
2. Open a new browser to sign in
3. Select the certificate If you are using a smart card, make sure it is inserted correctly.

I have deleted the applications, redownloaded Windows App (from Mac App Store) and an old version of Remote Desktop, but neither will let me dump my cache to try a to use my CAC smart card login again.

Answer 1

Try looking in your keychain and searching for an offending certificate of kind identity preference. Deleting mine then prompted me to select the cert again.

Hope that helps!

Answer 2

Do you have the Smart cards checked for the connection?

Answer 3

Hello,

I apologize for the delay in my response. I have been thoroughly investigating this issue, but unfortunately, I have not yet found a workaround.

It appears that this issue is affecting multiple users:

Certificate Validation Failed When Accessing Azure Portal/O365 - Training, Certification, and Program Support (microsoft.com)

Certificate Validation Failed (MAC) - Microsoft Community Hub

How to fix certificate validation failed on mac os using Azure - Microsoft Q&A

And we are currently unsure if it is a new bug in the Windows App. To help us better understand and address the problem, could you please provide the following information:

• The version of macOS on your Mac.
• The version of the Windows App you are using.

Thank you for your cooperation and understanding.

Best regards,

Karlie Weng

Answer 4

The above fix of deleting the offending certificate of kind identity preference fixed the problem for me. Thank you.

Answer 5

Thank you so much Karlie.

I am using Sonoma 14.3 and Windows App 11.0.5