sshuttle VS wsl2-ssh-pageant

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

doesn't work with latest gpg4win. There's an open issue, but it's not solved yet https://github.com/BlackReloaded/wsl2-ssh-pageant/issues/33. Has something to do with GnuPG version.

You should use the latest wsl2-ssh-peagent, which has a new --gpgConfigBasepath option to allow you to specify the .gnupg directory in Windows.

sshCommand = C:/utils/OpenSSH-Win64/ssh.exe

For GPG, the only things I've done is to use gpg-agent and set up a passthrough for gpg-agent to WSL2 for both OpenSSH and GPG via https://github.com/BlackReloaded/wsl2-ssh-pageant/ since I do development both natively on Windows and via WSL2.

Yeah, I've been using a Yubikey for a bit over a year and I'm already a huge fan of the way it works with SSH/Git. It's a bit more of a pain to set up with WSL2 since you need something like https://github.com/BlackReloaded/wsl2-ssh-pageant but it's absolutely worth the setup time.

I use PuTTY's pageant and https://github.com/BlackReloaded/wsl2-ssh-pageant to share keys between environments but you still need to enter your passphrase at power-on. Window's ssh-agent looks like a better solution. No need to re-enter the passphrase and no need to keep the private key around.