It was 2003 and I was a dedicated and exclusive Mutt user (this, before Gmail came along).
Due to some accidental press of the wrong key combination, somehow Mutt managed to take every single email in my Sent folder and combine it into one gigantic aggregate text document -- a record of all emails I'd ever sent from that account -- and turn this aggregate itself into an outgoing email, ready for sending.
What's worse, it took every address that had ever been in a To: field in any Sent mail and put them all as one big list in this aggregate email's To field!
With just one more keypress, had I accidentally then sent this, every person I'd ever emailed would have received a copy of every email to any person I'd ever sent.
Can you imagine the disaster? That I could concoct such an email accidentally was terribly frightening and that was the last year I ever used Mutt.