I'm having the same/similar problem. I was just searching
through recent posts to see if this is being addressed.
The problems I am having are:
1. Messages without attachments are hanging in the outbox
for an extended period of time;
2. Messages with attachments are hanging forever, and the
only way I can delete them is to move them to Drafts and
delete from there;
3. Often the message is sent but stays in italics in the
Outbox.
4. If I pull up sending details, it shows sending task
completed several times.
5. If the attachment is over 1MB, forget it, even though
my ISP allows up to 8MB (and, incidentally, my business
need is up to 8MB).
AAarrrggghhh!!
I am running Outlook 2003 with Business Contact Mgr on
Win XP Pro (and starting to wish I wasn't).
As a workaround, I have started to blind copy myself if I
am sending out of Outlook and if I have an attachment, I
am going out to my ISP's web mail and sending from there.
Pain in the .....