Let’s face it, running Microsoft’s remote desktop on Mac isn’t the best experience. There are mainly two Apps that you can use from Microsoft to remote desktop into any Windows machine. Microsoft Remote Desktop Connection Client for Mac Version 2.1.1 is an app that comes with the Mac Office 2011. Microsoft stopped bundle a newer version of a remote desktop client with Mac Office 2016, instead, you can get it standalone from Mac App Store. In this guide, we will only focus on the legacy Microsoft Remote Desktop Connection Client for Mac (latest v2.1.1).
After upgrading one of my work Mac to MacOS Sierra (10.12.+), Microsoft’s Windows Remote Desktop stopped working. “The Certificate or associated chain is not valid.” error will prompt, and answering “Connect” on “Do you want to connect to this computer anyway?” does not bypass this error. It will prompt again and you will end up in an infinite loop.
To be fair, this is an extremely old version of Microsoft Remote Desktop client, things that stopped working seems normal. But that doesn’t mean you should just give up, it’s still usable.
Go to Preferences > Security tab > and select “Always connect, even if authentication fails“
This bypass the check on verifies that if you are connecting to the “correct” Windows-based computer. Give it a try to see if this change works. If so, you can save the preference so next time you won’t need to change the settings again.