SSHuttle via Windows

Configure a Debian machine to route network through a Windows host using sshuttle.
Use case is a Windows PC connecting to a remote Debian server and using sshuttle to provide temporary web access to the remote machine.
Not all ssh setup and configuration details are included. Plenty of better places for that.

Windows Host (Gateway)

1. OpenSSH Server: Ensure the OpenSSH Server is installed and running.
2. OpenSSH Client: Ensure the OpenSSH Client is installed.
3. Python 3: Install Python 3 and ensure it is added to the system PATH.
   • Verify by running python --version in PowerShell.

Debian Machine (Client)

Run the following commands to install the necessary tools:

sudo apt update -y
sudo apt install openssh-client openssh-server python3 python3-pip pipx curl
pipx ensurepath
pipx install sshuttle

Note: You may need to restart your shell after pipx ensurepath for the changes to take effect. Note" Ensure a recent version of sshuttle is installed. Not all the older versions will work here.

Usage

1. SSH into the Debian machine.
2. Run the sshuttle command below to start tunneling traffic through the Windows host.

sshuttle -v --dns -r <WINDOWS_USER>@<WINDOWS_IP> 0/0 -x <WINDOWS_IP> --to-ns <DNS_SERVER_IP> --python python.exe

Parameters Guide

• -r <WINDOWS_USER>@<WINDOWS_IP>: The SSH connection string to the Windows host.
• 0/0: Proxies all network traffic (default route).
• -x <WINDOWS_IP>: Excludes the Windows host IP from the tunnel to prevent connection loops.
• --to-ns <DNS_SERVER_IP>: The IP address of the DNS server to use (reachable via the Windows host).
• --python python.exe: Specifies the Python interpreter to use on the remote (Windows) side.

Example

# Example with placeholders
sshuttle -v --dns -r user@192.168.1.5 0/0 -x 192.168.1.5 --to-ns 8.8.8.8 --python python.exe