I'd just gotten done typing why it's impossible to convince most people this stuff matters, and was responding to a comment that seems to be written with the assumption that man-made laws are the ultimate authority. So I'll admit to being a bit presumptuous, but I really do believe it to be a fact that most people will never see the need for technically-granted anonymity, and that these opinions simply aren't relevant when discussing such software.

Back to the technical, isn't this the point of Tor "bridges" ? Of course these don't work out of the box - they require finding out the address of one out-of-band and manually configuring it. Wider casual adoption of Tor would have also fixed the problem in this case (if the resulting Tor user list was too long to question everybody).

The whole point is that ending up on a shortlist means you are essentially caught. This kid may have gotten off by playing it cool. But translated into the dissident scenario, it's still a loss.

Given the proliferation of surveillance cameras, the coffee shop scenario becomes much harder. Assuming after-the-fact facial recognition is standard these days, it would only work if there were enough other Harvard students also on tape. Low latency is the mortal enemy of mix networks.