I have tried all of the below several times:

1.  Deleting from the "Progress" box - its still there and starts to try to send it again

2.  Quitting Outlook and holding down the "Shift" key when re-opening the program

3.  Working Offline

4.  Typing a code in to the Apple Script Editor that is supposed to delete all outbox messages.

This is incredibly frustrating as I studied computer science and I still can't fix this issue?!  From reading other Forums Microsoft has apparently removed the outbox from this version of Outlook in replacement of the "progress box".... crazy when the outbox already worked fine to show email progress but the progress box is completely lacking in any way to delete a stuck email.

Any other suggestions that I haven't tried?