Quoted:
If they're stupid enough to use a proxy to filter traffic but make it possible for web clients to go outside to an external proxy instead, then I want my tax dollars back.
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There are probably transparently proxying web traffic (all port 80 gets filtered/logged), but an external proxy could be on any port (3128 is the usual, but not hard to configure to some abitrary port number.)
They could use a tool to sniff packets to identify unauthorized proxies based on payload content, not port. But of course you could use SSH and tunnel your proxy in encrypted ssh packets. The network admin/snoop looking at this stream won't know if it's an interactive login, copying some files, encrypted peronsal telephone calls, or what.
However, I wouldn't want to be the one standing tall before the Man explaining why I was ssh-ing to random servers out on the Internet. "So I can proxy my unauthorized web traffic" would not be a good answer. "So I can watch my kids on the web cam" has a nicer ring, probably get a warning instead of immediate dismissal.
Cellphone with EDGE wireless internet, cabled (no bluetooth, the walls have ears) to a personally-owned laptop, while hiding in the john, that's the marignally safe way to browse at work without leaving a network/system trail. Alternatively, one might consider WORKING at work, and browsing at home.
The way technology is evolving, we may end up playing solitaire with old-fashioned paper cards to while away the dull hours