The private tracker works fine if the proxy is turned off. uTorrent never even queries the tracker since the tracker url becomes corrupted, as I said... even if you specify a URL with the private session id stripped off (as I did) the crash still occurs, so it's happening before processing the tracker reply most likely (the error messages utorrent spit out suggest it fails to establish an SSL session, maybe due to more corrupted memory). So it is clearly either due to Tor or due to uTorrent. Tor transparently wraps connections and using Tor with torrent files from public torrents works fine so I doubt it plays a factor. As a programmer I speculate that in some code path relating to proxies, the memory space holding the url and some SSL session data, and perhaps part of the stack or heap (or something that eventually causes the crash) is overwritten by accident when utorrent goes to connect to it. I normally use Tor directly so I did not think of using Privoxy as a workaround, I'll try that in the meantime, thanks. It might also explain why this issue hasn't been widely reported, out-of-the-box you use Privoxy with Tor. [Edit: Nope, I forgot Privoxy was cut out and replaced with Polipo I think. I'll try that.] [Edit: Boo, looks like Polipo might not handle CONNECT, or at least the FAQ indicates it's for HTTP traffic only. I'll try Privoxy instead.] [Edit: uTorrent does not crash or corrupt the tracker name when using an HTTP proxy, but it claims to be updating when Privoxy logs no such connection attempt. However I can manually connect using PuTTY through Privoxy, though for some reason Privoxy did not receive the expected from the private tracker (tracker immediately closed the connection, possibly it didn't like the exact way I connected via PuTTY), but the connection attempt at least logged in Privoxy's log window (enable debug 2 in the config to see that stuff). So HTTP proxy doesn't seem to work right either in uTorrent for tracker updates on the torrent I posted. Other connections through the HTTP proxy to uTorrent's update server and app server and to peers are logged.]