Mac Cannot connect to Windows PC using RemoteDesktop for Mac via VPN

Question

I have two nearly identically spec'd 2019 MacBook Pro's connected to company VPN. They can use interent, receive email, etc. so i know the network is working, however they cannot connect to other machines on this network via the Microsoft RemoteDesktop app for Mac. I have tried both the current stable release version, and the latest Beta version released Dec. 1, 2020.

Answer 1

I ended up solving this issue in the Network preferences of the two Mac devices.

The VPN needed to be manually assigned as the top of the order of networks in order for traffic to flow correctly through the VPN.

 > System Preferences > Network
Select the Gear Icon with carrot (see screenshot)
Select "Set Service Order.."
Drag VPN to the top of the list
Click OK
Click Apply
Live Long and Prosper

Answer 2

Hello @Caleb Denman

What's the error message when connection failed?

What's the OS of windows PC?

Please un-tick the checkbox " Allow connection only from computers running Remote Desktop with Network Level Authentication "
on Windows PC

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Best Regards
Karlie

Answer 3

Hi there,
Unfortunately that didnt fix the issue.
I have attached a screenshot of the error i am receiving on MacOS

The Windows PCs are currently running Version 2004 Build 19041.630 of Windows 10 Pro.