If that doesn’t work or if you need another trick, you can maybe do to your boss what I did to mine.

He was nagging us to lock our screens before walking away from our computers - which makes sense, given the elevated privs we had. Whenever he saw an empty seat with no screensaver on the monitor, he’d send out a false email to our group from that account - and that’s how the victim would realize his mistake.

One day my boss left his screen open, so I got to work. I created a batch file and edited the MS Word icon to point to the batch file instead of Word. Kept the icon itself of course so he’d have no idea it wasn’t directly opening word.

Now, the batch file, once run (minimized) would send out a DOS email message to our group, letting us all know that our boss intended to come to work in a sundress, and would do all our work for us for the next week. It would then open MS Word and exit.

The boss had no idea how those emails were being sent from his account, nor did he know what the trigger was. As far as he knew, every time he clicked on the Word icon, Word would open.

This went on for a while until he finally caved, and sent an email asking whoever boobytrapped his computer to come fix it.