Last updated on November 22, 2018
Desktop email clients, such as Thunderbird and Claws Mail, are preferred over their web counterparts by many professionals and power users due to their additional convenience and security. However, one big downside is that they often expose the sender's IP address to the receivers, since many SMTP servers record the sender's IP address and put it in the header, something similar to
Received: from [xxx.xxx.xxx.xxx] (my.example.com. [xxx.xxx.xxx.xxx]). This, unfortunately, puts the sender's privacy in great jeopardy, as an IP address can reveal so much information including location, ISP, and institution names.
To address this issue, one simple solution is to let the email client connect via a proxy. While a system-widely available proxy works for many users, some of us just want our email clients, but not other programs, to go through a specific proxy. In this post, I'll demonstrate how to use an email client automatically via SSH tunneling. The instructions are specifically tailored for GNU/Linux and MacOS users, as it involves some uses of UNIX commands and bash scripts; if you are on Windows, you can still follow the instructions with the help of Cygwin.