Kdavis,

The scenario you have described appears to be random. to aid in troubleshooting this issue to find what is causing sent items to hang in the Outbox, please supply some answers to the following questions.

1. What Account type is this user using? ( i.e POP3, IMAP, Exchange)

2. If this is a pop or imap configuration, what is the SMTP port being used and does the SMTP server require authentication?

3. How is this person connected to the internet? Is it a wireless connection? is there evidence that the connection is lost between outlook and the server?

4. Can you PING or TRACERT the recipient domains?

Hope this helps.