I've been doing something similar for almost 8 years now. I wrote a Ruby script to do the heavy lifting of tunneling all my TCP traffic through an HTTPS proxy.
I first wrote it to circumvent the firewall at a summer job to be able to connect to IRC, and I recently got it out of the dust to do something similar at my current job. I couldn't use anything pre-existing, because I was on a tightly locked down Windows system. This approach only required some kind of portable Ruby runtime.
Corkscrew does pretty much the same thing, but my script doesn't require an SSH server to run on port 443 and does away with SSH encryption for most connections. The latter can be either a good or a bad thing, depending on your use case.
It's about 160 lines of code, you can find it at https://github.com/wvdschel/ProxyBash.
I first wrote it to circumvent the firewall at a summer job to be able to connect to IRC, and I recently got it out of the dust to do something similar at my current job. I couldn't use anything pre-existing, because I was on a tightly locked down Windows system. This approach only required some kind of portable Ruby runtime.
Corkscrew does pretty much the same thing, but my script doesn't require an SSH server to run on port 443 and does away with SSH encryption for most connections. The latter can be either a good or a bad thing, depending on your use case.