sshuttle VS proxychains-ng

That's really good to hear! They got a (well deserved!) 100M investment recently. I didn't know it until recently, but apenwarr made some of my favourite tools (sshuttle, bup) and now tailscale! If you come across the podcast again, please post the link, I'd love to listen to it.

There are several ways suggested there. And as an alternative to SSH tunneling, you can also use sshuttle which is faster and easy to set up.

Have you seen sshuttle (https://github.com/sshuttle/sshuttle).

sshuttle Let's you route over ssh tunnels.

> Using openssl with a wrapper service?

One of tailscale's founders already built this: https://github.com/sshuttle/sshuttle

Sshuttle is an excellent tool that acts as a “poor man” VPN, allowing you to create a VPN connection from your machine to any remote server you can connect to via ssh. The exciting part is that it is not precisely a VPN and not exactly port forwarding. Internally it assembles the TCP stream locally, multiplexes it statefully over an ssh session, and disassembles it back into packets at the other end to achieve data-over-TCP, which is safe. Useful if your VPN breaks down.

I generally meant collocate a HTTPS service with a VPN service. I was thinking of a setup I used to run which was something contrived with haproxy sslh and sshuttle. This exploits the property of who talks first in the protocol

Chrome lets you set a proxy but not a username or password but I have a proxy that can only be authenticated with a password. I tried using proxychains-ng but that doesn't work with Chrome https://github.com/rofl0r/proxychains-ng/issues/45.

You should use proxychains4, you can build it yourself https://github.com/rofl0r/proxychains-ng, I like using sshuttle project, kinda like a pseudovpn https://github.com/sshuttle/sshuttle