Mailbox won't send until I quit & reopen

Ok some very strange mailbox behavior a month ago - mail kept randomly picking up old emails from my trash & other folders and redepositing them into my inbox, and also would randomly resend some of them to users. No idea how or why that started... cleared off all downloads on my computer, reset my Safari, checked every setting in my mailboxes more than a dozen times and saw nothing unusual. That stopped after a few days... however, ever since the only way mail will send is if I hit send, then quit mail, then reopen. If I don't quit, the composed msg to send totally disappears - not in outbox, not in sent, not still open to view. As soon as I reopen the mail app, it immediately sends without me doing anything at all. ???? Help, I'm so not a techie and this is my first Mac so I'm lost!

Hi fijikaren, and a warm welcome to the forums!
I see a couple of things to try...
This can fix myriad Mail problems...
Safe Boot from the HD, (holding Shift key down at bootup), it will try to repair your Disk Directory while the spinning radian is happening, so let it go, run Disk Utility in Applications>Utilities, then highlight your drive, click on Repair Permissions, then move these folder & file to the Desktop.
Move this Folder to the Desktop...
/Users/YourUserName/Library/Caches/Mail/
Move this file to the Desktop...
/Users/YourUserName/Library/Mail/Envelope Index
Reboot.
If that doesn't help, open System Preferences>Network... do you get a "Your Settings have been changed" warning?

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