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Outlook 2013 Have to Exit and Restart to Send Mail

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I'm using Windows 7 64 and Office 365. I rely on e-mail for primary business communication. Since switching to Office 365, I've had incidences where I've "sent" e-mails before leaving, then returning 3 hours later to find the e-mails never left the Outbox.

This happens constantly - every day, multiple times.

The bottom of the window reads ALL FOLDERS ARE UP TO DATE and CONNECTED TO MICROSOFT EXCHANGE, and the icon in the tray at the bottom of the screen has no little yellow triangle with exclamation point, and yet when I hot SEND/RECEIVE the e-mails won't leave the Outbox.

I've discovered that exiting and then restarting the program seems to temporarily set sending outbound e-mails as top priority, but then after a few minutes it goes back to ignoring mail in the Outbox, while syncing other folders.

Is anyone else experiencing this extremely frustrating and counter-productive problem?

Thanks for your help,

Dennis

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