I had a similarly hilarious experience a few years back, related to a distribution list but compounded by trying to recall a message. Someone from accounting had both Outlook Web and personal web mail open at the same time. He was composing an email about SOX compliance to all managers in the US for a large national company. Apparently he was also composing an explicit personal email to his girlfriend about what he had planned for the bedroom that night. Somehow his wires got crossed and the explicit email got sent to all the managers (I assume his girlfriend got the SOX email). I wouldn't have even read the email had he not tried to recall the message, which on some clients deletes the message, but on others, it just sends another email about trying to recall the email. Needless to say, he was fired on the spot.