1) Compose the message
2) Click send
3) Watch spinning wheel by "Sending..." for 5 minutes, then see it time out
4) Quit Mail.app
5) Re-open Mail.app
6) Observe message sitting in Outbox
7) Attempt to send message again
8) Message still in outbox, no sign of attempting to send. Yell and swear
9) Try sending message about 15 more times
10) Quit Mail.app
11) Re-open. Try to send message 5 more times.
12) Fail. Quit app again
13) Re-open, try to send message. It finally works, cheer when you hear the airplane noise.

Does anyone else have to go through all this when sending about 1 in 5 messages through Mail.app and MobileMe?