Spent some time looking at a rather bizarre problem for somebody today. Messages in Outlook 2003 did not leave the Outlook and enter Sent Items, even though the recipient actually received the item. Only happened with sizable attachments (1 MB+) and as you can imagine, this is a bit painful when you end up sending the same attachment 20 times to some poor unsuspecting subject.
After the generic troubleshooting and machine health checks, the finger ended up pointing in the direction of Trend Micro's Internet Security 2010. For some reasons it is unable to deal with sending large attachments. I turned off the outgoing SMTP scanning and all was well. Having spent a bit more time on it afterwards I found the following:
http://esupport.trendmicro.com/Pages/Emails-with-attachments-over-1MB-in-size-remain-in-my-Outbox-even-thou.aspx
Quite why they can't fix this properly I don't know, but there you go, hope it saves you the two hours it took me to find the root cause.
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