I love my Pi Zeros. I think every hacker should have one in their toolbox. When I got my firs Pi Zero several years ago, I used a USB-TTL serial adapter to connect to the console UART on pins 8 and 10 of the Pi header. Once I learned how to setup the Zero as an ethernet gadget, things were a bit easier. However updating software was still a cumbersome process of downloading files to the host computer and then using scp to transfer them to the Pi. This blog post documents how to setup the Pi to use a SSH reverse proxy so utilities like git and apt work.
When I got my first Pi Zero, I chose the Pi OS Lite image. I decided to update to the March 4, 2021 release, and this time I used the Pi OS with desktop because it includes development tools like git. I followed the ethernet gadget setup instructions, modifying config.txt, cmdline.txt, and creating an empty file called "ssh". The next step is to configure the multicast DNS component of Zeroconf. As mentioned in the Adafruit instructions, if you are using Windows, the easiest way to do this is installing Apple's Bonjour service.
To use a reverse proxy over ssh, Windows users can't use putty as that feature is not supported. OpenSSH supports reverse socks5 proxies as of version 7.6. For connecting from Windows, I installed MSYS2, including OpenSSH 8.4. On Windows 10, WSL is probably the easiest option. To connect to the Pi and enable a reverse socks5 proxy on port 1080, enter, "ssh -R 1080 firstname.lastname@example.org".
Once connected to the Pi, set "http_proxy" to "socks5h://localhost:1080". The "h" at the end is important as it means the client will do hostname (DNS) resolution through the proxy. I added the following line to .profile to set it every time I login:
Programs such as git and curl will automatically use the socks proxy when the http_proxy environment variable is set. Note that github defaults to showing https URLs for repositories, which need to be changed to "http://" for the proxy to work.
The last configuration I recommend is setting the current date, since the Pi does not have a battery-backed RTC. I normally use ntpdate from the ntp project for manually setting the date and time on Linux, but it does not work with a socks proxy. After some searching I found a suggestion of using the HTTP Date: field from a reliable internet server. The command I use is:
date -s "`curl -sI google.com | grep "^Date:" | cut -d' ' -f3-7`"
Once the Pi Zero is configured and has the proper date and time set, I recommend running "apt update". If everything is working properly, it will use the socks5 reverse proxy to connect to the raspbian servers and update the local apt repository cache.