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All Kind of MS Outlook Technical Problems Call To Us Toll Free 1-855-517-2433. Friday, 10 January 2014. How to Email stuck in the Outbox for Outlook 2010. If an email seems to be stuck in your Outbox, continue on to the steps below to either clear the stuck message or see if a bad connection to your mail server is stopping the message from being sent. In Outlook, click the. Tab, and then click.