I saw an interesting talk by Dan Kaminsky at Def Con that touched on some ideas for censorship detection. He mentioned OONI-probe and talked about his project CensorSweeper. It tests blockedness of web sites by making cross-domain requests for favicon.ico and displaying them in a minesweeper-like grid.
http://www.censorsweeper.com/ https://www.hackerleague.org/hackathons/wsj-data-transparency-code-a-thon/ha...
He also mentioned something, which unfortunately I didn't follow very closely, about using Flash sockets to spoof HTTP and HTTPS headers. I think the gag here was sending these spoofed connections to a server you control (so you can answer the crossdomain policy requests without which Flash Player will refuse to connect), but you give it a Host header of a censored site or something like that.
http://miriku.com/wp/2012/07/decon-day-3/comment-page-1/#comment-1416
Unfortunately I don't have the conference DVD which presumably contains the slides he used, but videos usually show up online after some number of months.
David Fifield