I have had (and posted) this exact problem before and it just went away last time. I am unable to send a file of any reasonable size (say 3 meg) in thunderbird. I'm running a pop account, I can send large files from WEB mail. Many suggestions say go to 'tools' - 'options' but I have no 'options' listed anywhere. This problem has been going on a couple months. There has to be an option or something I'm doing wrong here. I would appreciate any suggestions. Probably something dumb I'm doing but I cannot figure out what it is. I send large files using filezilla almost daily. Sending of the message failed. The message could not be sent because the connection to Outgoing server (SMTP) gator3028.hostgator.com timed out. Try again. Port 465, the default I believe. Lost here, if you got any ideas i would appreciate it.