Setting up a torified ssh tunnel to a squid proxy

[fwall]

Hello!

I would like to connect to an anonymous squid proxy that we have set up on a deniable VPS using a torified ssh tunnel

I have this working using a test virtual machine and a test server

torsocks ssh -L port:server:port

sets up the tunnel and

who

shows me connected from an TOR exit

then using firefox with the http proxy set to localhost:port allows me to browse and the ip is that of the proxy

In a Whonix WORKSTATION I can

ssh -L port:server:port

the connection (again) will be torified and I can browse in firefox using the same browser settings

My questions are

1. Should I be using the TOR browser instead of firefox esr and if so - how to make it use the ssh tunnel to the proxy because simply setting up the proxy as in firefox doesn’t seem to work

2. Should I be setting up the tunnel in the gateway? What is the advantage of doing this? (because it looks like quite a big deal)

[Patrick]

Should I be setting up the tunnel in the gateway?

The tunnel?

And in the gateway, for this type of setup, most likely a strong no.

If you setup an ssh tunnel from Whonix-Gateway to the VPS, you actually de-anonymize yourself. Setting up a ssh tunnel in Whonix-Gateway results in user -> ssh -> Tor -> Internet. Some people want this to have a longer tunnel length but in your case that would be a huge fail.

See:

Tunnels/Introduction

Should I be using the TOR browser instead of firefox esr and if so - how to make it use the ssh tunnel to the proxy because simply setting up the proxy as in firefox doesn’t seem to work

It’s Tor not TOR.

Always prefer Tor Browser over icewasel. (Why? -> https://www.whonix.org/wiki/Tor_Browser)

I recommend strongly against X11 forwarding through ssh due to keystroke fingerprinting. (At risk as soon as the VPS turns malicious.)

Also applicable to you:
https://www.whonix.org/wiki/Remote_Administration