I have a user of Outlook 2003 where every night at about 11:50 PM he starts
an email message to his supervisor to give him the night shift update. It
takes him until after 12:00 to complete the message with all his numbers and
such. Almost every night when he goes to send the message Outlook hangs on
him. He has to kill Outlook. When he opens Outlook the message is in his
drafts folder, but it still will not send. He then has to copy the part of
the message that did get saved in the drafts folder and then paste it into a
new message in order to complete and send it.

I have been asking him to see if leaving the message open for an extended
time is the problem, but no matter how long he leaves it open before or
after Midnight he is fine. It is only when he crosses Midnight even for as
little as 10-15 minutes.