For the past few months, my MacBook Pro has been my daily driver. As a Systems Administrator, I work with both Linux and Windows Server systems on a daily basis. I usually have multiple tabbed RDP windows open for Windows Server in a Windows VM running on my Mac, with Remote Desktop Manager (highly recommend this product).

However, there are many times when I RDP to systems direct from my Mac with the “Windows Remote Desktop Connection for Mac” software. The first time I tried to RDP to a Windows Server, I got the following error when trying to connect:

After many tries and much searching around online I was unable to get it to work. You’ll find many forums and questions about this. None of those solutions worked for me. The fix that worked for me was due to the security settings of our domain for RDP sessions. We do not allow RDP sessions to remember passwords, as a security precaution; however, from the above screenshot I’d have no way of figuring it out.

Here’s what you do. Go to RDC > Preferences > Login tab. Make sure you do not check any of the boxes and the only information you have is your Username and Domain, like this:

Close the box and then try your RDP connection again. Just enter your password, again don’t check the boxes and it should work.

If you still have an issue connecting, go back into Preferences > Security and set the radio button to “Always connect, even if authentication fails”:


Here is the Group Policy setting that if ENABLED, will cause this issue for you:

Policies\Administrative Templates\Windows Componets/Remote Desktop Services/Remote Desktop Session Host/Security

“Always prompt for password upon connection”

Hopefully this may help other Mac users trying to connect to the Windows Server world that have issues with RDP. Thanks for reading.

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