Outbox populating with old sent messages

I am on a macbook with OS 10.5.8. My outbox is populated with an email response that I successfully sent to the recipient a month ago. When I check for new mail, it resends that message in the outbox to the recipient and the next email I had sent after that a month ago populates the outbox. I have been resending old emails everytime I check for new mail. Deleting the mail in the outbox only makes the next old email in line populate the outbox. Does anyone know what I can do to fix this? Thanks!

I'm seeing the same kind of [mis]behavior. The outbox ALWAYS has one email in it which is chosen from (usually) the SENT folder, but not always. If I delete this one email, the outbox count remains at zero and selecting any other folder and returning reveals a new bogus email stuck in the outbox.
I tried deleting the OUTBOX / mbox folder but that makes no difference.

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