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?))
Windows 11 Client will not connect through Remote Desktop Gateway (Server 2012 R2) to Windows 11 Endpoint
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.
We have a similar issue. Try disabling UDP on the Remote Desktop Gateway and see if that works. You can also test if this is a UDP issue by [adding the following registry key to a client which is failing to connect: HKCU/Software/Microsoft/TerminalServerClient: Type: REG_DWORD, Name: RDGClientTransport, Value: 1 (Decimal). This will force the client not to use UDP.
We've found that disabling UDP on the server yields inconsistent results (though it is a better solution). Adding the above registry key on the client is not a great solution, but it works consistently and will help you determine whether or not this is an issue with UDP. Source.
Thank you @Alex Rourke . Turns out, my issue was much more basic (and I feel embarrassed, but I must be honest). I tried what you sent me, and I got a new error, that the Remote Desktop Gateway could not be reached.
We us a non-standard port for our RDG. Turns out, I typed in the wrong port, and I guess switching to legacy connection allowed the appropriate error to emerge.
Excuse me while I got cry in a corner for a minute and move on with my life.
Seriously though - thank you for your time. I now can say with certainty our RDG does not use UDP.
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