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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...

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...