David Price wrote:

Several times recently I have sent an email with attachments that
sits in my Outbox as if its not being sent but is actually being sent
repeatedly, much to the annoyance of the recipient. Any ideas?

1) DIsable all mail scanning by your antivirus program.
2) Lengthen the server tiomeout value on the Advanced tab of your account
properties.
3) Lenghten the send/receive interval.
--
Brian Tillman