I was mostly helping people with Tor-related stuff and didn't have time to get a sense of the other usability issues out there in thinks like whole disk-encrypt

I was mostly helping people with Tor-related stuff and didn't have time to get a sense of the other usability issues out there in thinks like whole disk-encryption and PGP. There is a very literal UI bug that is also a security problem in the Tor Browser Bundle. If you resize the Firefox window, you increase your browsers uniqueness & thus make you easier to identify. Try this by switching off a toolbar and noticing the difference at panopticlick.eff.org Getting a piece of software like Pidgin to work through Tor was a challenge for many. The concepts of 'localhost' and sockets and a TCP-stream was challenging to get across. I don't really know the answer to this problem. These are hard issues to solve with software and the best we've got so far, I think, is education. If I had to imagine a piece of software: something like a packet filter that could go into 'incognito mode' set-up a transparent proxy and automatically flag packets that could reduce one's anonymity or reveal one's identity, then recommend steps to take in the relevant applications to get around that. It's not a completely thought through idea but maybe someone will come along and read this and it would spark the solution in their mind. There are more bugs than people, check out trac.torproject.org and see what you can do. The #tor irc channel on irc.oftc.net & tor-talk@lists.torproject.org are good places to ask questions.