Email stuck in Outbox

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Outlook version
Outlook 2010 32 bit
Email Account
Exchange Server
Hello All,

I'm having an issue with a user who has to constantly rebuild his Outlook profile because his email gets stuck in the Outbox. He is on Outlook 2010 with 2 email accounts connected to his Outlook profile (not "opening additional mailbox" under advanced) The second account is on the same Exchange server as his primary.

The emails that get stuck are with the second account. While he is having trouble with the second account, he can still send out emails on the primary account. Clicking Send/Receive reports back as successfully but it isn't becasue the emails are still in the Outbox. The one thing I do notice is the status on the primary account is "Connected to Exchange" while the status of the second account is just "Online"

The problem can be fixed by recreating his profile but it is only temporary as it will allow him to send email from both accounts temporarily. Sometimes it will break after a day or last as long as a week. Seeing that he can send emails from both accounts once the profile is created, this doesn't seem to be rights issue.

I've tried repairing the installation with no avail so I'm stuck and out of ideas. Hopefully someone here has dealt with this issue in the past.
I just tried it out in Safe mode and the item is still in the Outbox even after a manual send and receive. To answer your other question, once it gets stuck the only resolution that seems to work has been to recreate the Outlook Profile. Then it will work for a period of time until it gets stuck again. Again, this is only for the non-primary email account.

Do you have any insight on the Connected to Exchange vs Online status in Outlook? This is Outlook 2010 by the way.

I thought Online status should be classic mode, not cached. 'connected to exchange' indicates cached mode. I'll double check it though.

I know there are issues with Outlook 2013, it sounds like the problem affects outlook 2010 too as your description is pretty much identical to the other complaints I've seen. I'll see what i can find out about it.
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