Are you in the outbox when this happens?
http://www.slipstick.com/problems/outbox.htm

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Diane Poremsky [MVP - Outlook]
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"JSoul Rules" tkd-in-the--city@yahoo-dot-com wrote in message
...
Oddest thing. On some messages when I reply, the message will go into
the outbox and quickly change from italicized (send queue) to regular
type face (in draft mode and not sending.) When I click send again it
becomes italicized for a split second and then goes into the draft
mode. I can't explain what is going on and why it affects some
messages and not others. I have to recreate the message and sometimes
it works and other times the same thing happens. Anyone have this
weird behavior?