Outlook 2007: Some mails will not leave Outbox?

My wife uses Outlook 2007 (SP1) to access her two Hotmail accounts (one personal, one business). Sometimes, a message she sends will just stay in her outbox. Once this happens, OTHER messages will go out, but that message continues to "stick" in the outbox until we delete it.

Sometimes the message gets delivered, even though the message is still in the outbox.

I have no repro steps because we don't see any commonality in the messages that "stick" and it happens infrequently. It happens with all kinds of items (messages, meeting requests, etc), and has happened with either account.

We're currently seeing this with OL2007SP1 on Vista SP1.

I have Outlook Logging enabled, but the logs corresponding to the Send/Receives I've been doing don't seem to show anything.

Has anyone seen anything like this or know how I might go about diagnosing?

Thanks!

 

Why would one use Outlook to get Hotmail? Why not just get it with Hotmail?

Sounds a bit dicey.

I do have a Yahoo Mail account for use with one business relationship, which I want to keep at arms length. When I get mail there that I want to keep, I just forward the mail to my Outlook email address. Similarly, if I am sending to that party using the Yahoo Mail, I just send Bcc to my Outlook email address.

>>RSM

 

Outlook calendar works with ActiveSync/Windows Mobile Device Center.

I've found a possible workaround, though still no lead on the cause:
1. open the stuck message
2. open each recipient's properties (NOTE: each recipient is an Outlook Contact)
in each case, at least one recipient's email address is NOT underlined when viewed as a contact.
3. click "Check Names" on the Contact
(address becomes underlined)
4. save/close the contact
5. DELETE the recipient from the email's To/CC/BCC line.
6. Add the recipient back in

...now the message will send as normal.

Some of the Contacts were imported from Windows Address Book or came off third-party applications. I wonder if some tiny piece of SOME of the addresses was not well-formed? Hmm...