Was this a genuinely dumb oversight on the student's part? Harvard WiFi requires students to log in with unique IDs to gain access (http://www.fas-it.fas.harvard.edu/node/189), so Harvard can monitor and log all of your traffic.

Does this mean Harvard could in theory have this transmission recorded as it goes in to the TOR network? Would something as simple as going across the street to Panera Bread have thwarted this kind of investigation?

I'm really curious if the flaw in this kid's plan was that obvious.