Outlook won't send emails

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Ahawk

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Occasionally an outgoing email would hang up in the outbox. Now it is happening the majority of the time and the problem is Outlook doesn't assign a date to the email. I can copy the message into a new email and it will get a date assigned but this may have to be done 2 or 3 times. This occurs with both new emails and reply's. Is there a setting that has been changed? Is there a fix for this? Thank you.
 
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