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I'm currently struggling with this task:

Changing Windows machines have to RDP over SSH to a Raspberry behind changing foreign networks.

So there has to be machine in-between the Windows host and the Raspberry.

I setup a Linux VM in our DMZ and also the FW policies + NAT rules.

Things that work:

  • I can reverse SSH from the Raspberry to the Linux VM in the DMZ
  • When Windows and Raspberry are in the same network, RDP over SSH works

Things that I can't figure out:

Tunnel RDP through Linux VM through reverse SSH tunnel to the Raspberry

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After digging more into this I figured it out!

Raspberry:

ssh -N -T -R33898:localhost:3389 Linux-VM

Windows (using putty):

Destination: Linux-VM:22

SSH > Tunnels> Forwarded ports: L4444 localhost:33898

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