When I am at work we have very tight firewalls, as a way to get around them and perhaps even gain some increased anonymity myself and many of my co-workers have set up SSH tunnels to our own hosted external Linux machines and use them as SOCKS proxies.
The most rudimentary setup might look like this, although some people have slightly more complex or simplified setups:
localhost SOCKS proxy -> SSH tunnel -> sshd on port 443 -> internet
SSH is listening on port 443 because outgoing requests on port 22 are blocked.
For those interested some people use
stunnel but most people are using
plink invoked like this:
plink.exe -N -D localhost:7070 -l user -pw password -P 443 remote-server.com
My question is, what does network traversing this tunnel look like to a network admin at our company? Does it merely look like "far too much ssh based traffic on port 443" which might rouse some suspicion, or can they actually see the nature of the requests?
What level of anonymity am I getting through this method, is there a better way?