I’m looking to try some hands-on experience setting up proxies. However, the proxy I want to setup is a bit unique. My end goal is to be able to do the following:

• Connect a Raspberry Pi to a network using Ethernet or Wi-Fi
• Automatically have the Raspberry Pi (as soon as it is powered on and connected) send its own public IP address (and other relevant proxy information, where applicable) to a home server (and periodically retry sending this information if the server is down)
• Be able to proxy my connection from a separate network through the Raspberry Pi (by simply entering in the IP address and port as a normal proxy) so that my public IP address will now show up as that of the network the Raspberry Pi is connected to

I want to avoid configuring port forwarding for networks the Raspberry Pi is connected to. I can configure port forwarding for the network my home server is connected to, but if possible I would like to avoid that as well (for convenience and security).

I also want to avoid using a third party service (e.g. Linode) to manage the proxy for me. I want the Raspberry Pi to do all the work here, ideally using open source software such as Privoxy or Squid. I want this to be an HTTP proxy. If possible, I would like to encrypt the proxy connection.

I’m not sure if any of this would be possible without port forwarding. Maybe some sort of reverse proxy would help with this. Like with most things, I understand how a proxy such as this could have the potential for misuse. I’m making this post for educational purposes only, so that I can better my understanding of proxies and network security.

Any guides or videos on how to set this up are greatly appreciated. I found a few, but none quite capture what I’m describing here. Most don’t talk about using this across separate networks, only local networks.

Thank you!