Setting up an SSH server to proxy connections on Windows

cygwin_ssh_proxy.md

Setting up an SSH proxy on Windows

No administrative privileges required.

Steps:

1. Download Cygwin setup application from https://cygwin.com

2. Run Cygwin setup file

   • Select “Install For Just Me”
   • In the Search box type “openssh” - Then expand net, and click on the openssh line twice until 7.4.x appears in the “New” column. You need OpenSSH 7.4.x as in 7.5.x the ability to run sshd as a non-administrative user was removed. Also, if you re-run the Cygwin setup, make sure you do not upgrade your OpenSSH server binaries.
   • Click Next then Next to install OpenSSH and other required Cygwin files.

3. Once the install has completed, open a Cygwin Terminal and type:

   ssh-host-config

   Respond to Queries as follows:

   *** Query: Are you sure you want to continue?  (Say "no" if you're not sure
   *** Query: you have the required privileges) (yes/no) yes
   
   *** Query: Should StrictModes be used? (yes/no) yes
   
   *** Query: Should privilege separation be used? (yes/no) no
   
   *** Query: Do you want to install sshd as a service?
   *** Query: (Say "no" if it is already installed as a service) (yes/no) no
   

   Then run:

   vi /etc/sshd_config

   Then change the line

   #Port 22

   To the port of your choosing such as

   Port 2987

4. Start the ssh daemon:

   /usr/sbin/sshd -D

   -D means keep sshd running in foreground so you can monitor it.

5. Next run this command from your local machine:

   ssh username@host.domain -p XXXX -D 8080 -C -N

   -p specify port your ssh server is running on

   -D specify the local port you want to setup as a SOCKS proxy

   -C enable compression

   -N don’t need an interactive session, just start proxy

6. Finally, configure your browser to use the SOCKS proxy for all connections