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CalebDenman-8802 asked RyanKinealy-3805 published

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

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.

remote-desktop-client
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Thanks! That worked for me!

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CalebDenman-8802 answered RyanKinealy-3805 published

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
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You're the best that fixed the issue

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KarlieWeng-MSFT answered KarlieWeng-MSFT edited

Hello @CalebDenman-8802

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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Karlie


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CalebDenman-8802 answered CalebDenman-8802 commented

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.

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Hello @CalebDenman-8802

Good day!

I'm just following up to make sure you received my last reply.

You can enable email notifications for a variety of different events in Microsoft Q&A:
https://docs.microsoft.com/en-us/answers/articles/67444/email-notifications.html

If you have any further questions or suggestions about this case, please let me know.


If the Answer is helpful, please click "Accept Answer" and upvote it.
Best Regards
Karlie

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Hello! I did read these articles but neither of them were related to my particular situation. I have posted another comment below with what fixed my issue.

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