Hello, I have experimented with file transfer using the Tor IM Browser Bundle, with files (already encrypted) from 1K to 1M, in these ways:
1) upload and download the file to a free Internet filehosting service ( mediafire.com), 2) email the file as an attachment, and 3) send the file during a Pidgin private conversation. In the first two cases, the download attempt sometimes pops up a warning message that a "NOT Tor safe" external application must be launched. Other times, the warning does not appear. I can't distinguish any pattern as to when the warning does or does not appear. There's a different launch problem in Pidgin. If you click on the "Authenticate" link to authenticate the other party for a private conversation, Internet Explorer gets launched without warning (this doesn't happen if instead you use OTR from the menu). Also, the file transfer sometimes completes, and sometimes you get a message saying that one side or the other cancelled the transfer (even though that didn't happen); whether the transfer is cancelled seems independent of the file size. Any help with these issues would be greatly appreciated. Luis

