Windows 11 Client will not connect through Remote Desktop Gateway (Server 2012 R2) to Windows 11 Endpoint

Ethan Wade 0 Reputation points

I have been slowly testing Windows 11 well in advance of the Windows 10 EOL.

I am stumped on a very specific issue.

I am running Windows 11 Home machine. I use it to remotely access a Windows machine inside a local domain, through a Remote Desktop Gateway (Server 2012 R2). I am able to remotely connect to a Windows 10 Pro endpoint, and the Server 2012 machine itself through the RDG (checked off site to ensure I wasn't accidentally bypassing the RDG server).

However, one end point is running Windows 11 Pro (22H2 - 22621.1702), and it will NOT connect from the Windows 11 Home machine when going through the Remote Desktop Gateway. When I am within the local domain, I can directly remote access the Windows 11 Pro machine, but somewhere between RDG > Windows 11 Pro machine, it is just not going past.

I also pulled out an Windows 10 Home machine, and THAT one was able to connect through RDG to the Windows 11 Pro machine.

I have searched and tried all the fixes (GPO and Registry Edit to disable UDP on the Windows 11 Home client), but nothing will work to get me from Windows 11 > RDG > Windows 11.

Windows 10 > RDG > Windows 11 -- Works

Windows 11 > RDG > Windows 10 -- Works

Windows 10 > Windows 11 (Local) -- Works

Windows 11 > Windows 11 (local) -- Works

Windows 10 > Windows 10 -- has always worked

Windows 11 > RDG > Windows 11 -- Does Not Work

I'm a bit at wits end because we use RDG pretty heavily as employees are off site to access local files/software.

Unless someone has a great fix they want to share that magically worked, I'll probably be waiting to buy new Windows 11 laptops until whatever bug this is gets fixed. As said above, I have also tried the Disable UDP fix, and nothing. I've even (for funsees) opened up UDP Points on the Endpoint (not the RDG Server, that's HTTP with SSL) and disabled UDP on the endpoint as well...

Any help is appreciated -- Hoping we can get an actual fix soon, because I can't "roll back" to before 22H2 because the Windows 11 Home machine is new.

Thank you,

Windows Server 2012
Windows Server 2012
A Microsoft server operating system that supports enterprise-level management, data storage, applications, and communications.
1,556 questions
Remote Desktop
Remote Desktop
A Microsoft app that connects remotely to computers and to virtual apps and desktops.
4,328 questions
Windows 11
Windows 11
A Microsoft operating system designed for productivity, creativity, and ease of use.
8,595 questions
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  1. Ethan Wade 0 Reputation points

    TL:DR - RD Gateway address port was incorrect. May I be a cautionary tale to always check the simple things ((is it plugged in? is it turned on?))

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