SSH RDP Tunnel and Port Connection

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Tried doing some research but can't really figure out the solution (or how to troubleshoot further) for this problem.

Objective and Reasoning for setting this up:
SSH Tunnel RDP from work to home computer. At work, most ports are blocked, but I am able to use SSH.

Set-Up:
Macbook Pro (at Work) –> Internet –> HomeModem –> SSHserver and Windows 10 Pro

I am able to connect directly to Windows 10 (from a friends house or local lan) without any issues. When I connect from WAN (not at work) I have port forwarding on my router at home setup for 338900 –> 3389 Windows 10 and 22 –> 22 SSHserver

I am able to connect to my SSHserver (Debian 8) from work and everywhere without any issues.

Attempts:
From my mac I have tried:

ssh -p 22 -L 3400:192.168.1.2:3389 root@WANIP | RDP: 192.168.1.2:3400 = no connection

ssh -p 22 -L 3400:192.168.1.2:338900 root@WANIP | RDP: 192.168.1.2:3400 = no connection

ssh -p 22 -L 3400:WANIP:338900 root@WANIP | RDP: WANIP:3400 = no connection

All these attempts have been made from a WAN connection where I can just connect using: RDP WANIP:338900 = connection

Any direction and help is greatly appreciated.

Best Answer

ssh -p 22 -L 3400:192.168.1.2:3389 root@WANIP

it's a correct command. I just checked in my environment. I have used the following command to create ssh tunnel

# ssh -L 192.168.1.6:3389:192.168.88.176:3389 alex@WAN.IP -p 2222
# netstat -an | grep 3389
tcp        0      0 192.168.1.6:3389            0.0.0.0:*                   LISTEN

After that I'm able to connect to 192.168.1.6:3389 via RDP.

On Debian you should check file /etc/ssh/sshd_config. There could be some restrictions

Match User alex
    X11Forwarding no
    AllowTcpForwarding no

On your mac you should check /etc/ssh/ssh_config for the same restrictions.

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