PaulE wrote:

This will
display for many minutes, even on a 0.5 Mb file. Then the detailed
status message will show that the message was not sent because of an
SMTP time-out. However, in many cases the recipient DID get the
file. If I walk away from the computer and let Outlook do as it
pleases, it will send the file MANY times to the recipient but each
time it stays in the outbox due to an SMTP time-out error - hence
Outlook tries to send it again.

In addition to Vijay's suggestion, lengthen the server timeout value on the
Advanced tab of your account properties pages.
--
Brian Tillman