Lost all a CIO's emails during an Exchange Migration
I once had to complete an AD and Exchange migration for a company. I don't recall the reason why exactly, but they needed to move to a new AD so a full migration was necessary.
When I configured the new Exchange environment, I set up some basic policies - you know, like remove all mail from the Deleted Items folder after 30 days etc.
A week or so after the migration was completed, I got an urgent "please explain" email from the CIO, he wanted to know why I was so incompetent that I had managed to lose all his emails.
Naturally I went straight to the logs to see that yes all X number of items had copied across, so I went to question him as to what emails he was referring to. At which point I learnt that he, no shit, stored every single email he wanted to come back to in the 'Deleted Items' folder. On their previous server they had no policies so they stayed there until he deleted them a second time. I never could get my head around his logic that this was a good place to store them..
Anyway, luckily I still had a PST of his old mailbox, so disaster was averted. But what a muppet.