Mail duplicates sent MESSAGES?

Since about two months I had three occurences where I sent an email to a person with text and maybe an attachment, shortly after I sent another email to someone else...with new body and all. HOWEVER, it sends out my first email with text, attachment to the second recipient specified. My second email (the intended one) is nowhere to be found. Not in drafts, certainly not in the "sent" folder.
Anyone else having this problem?
Thanks

If I’ve understood it correctly, this problem is caused by some index corruption that makes messages to randomly appear in a mailbox different from where they’re supposed to be. If that mailbox happens to be the Outbox, Mail thinks they’re waiting to be sent and dutifully proceeds to try to send them.
Verify/repair the startup disk (not just permissions), as described here:
The Repair functions of Disk Utility: what's it all about?
After having fixed all filesystem issues, if any, and making sure that there’s enough space available on the startup disk (a few GB, plus the space needed to make a backup copy of the Mail folder), try this:
1. Quit Mail if it’s running.
2. In the Finder, go to ~/Library/Mail/. Make a backup copy of this folder, just in case something goes wrong, e.g. by dragging it to the Desktop while holding the Option (Alt) key down. This is where all your mail is stored.
3. Locate Envelope Index and move it to the Trash. If you see an Envelope Index-journal file there, delete it as well.
4. Open Mail. It will tell you that your mail needs to be “imported”. Click Continue and Mail will proceed to re-create Envelope Index -- Mail says it’s “importing”, but it just re-creates the index if the mailboxes are already in Mail 2.x format.
Note: For those not familiarized with the ~/ notation, it refers to the user’s home folder, i.e. ~/Library is the Library folder within the user’s home folder.

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