Hang on there...........
I have a bet with a buddy. I have social engineered him and found out he has a excel spreadsheet with all his passwords on it
He may not know what you are going to do, but if you have a bet he will know you are going to do something. He may well have sought expert advice elsewhere?
He has no idea that I am going to do this.
He just has passwords for his personal stuff he doesn't have access to anything of consequence at work
Errrrrr, your network isn't "of consequence"? He is not using VPN............he doesn't know anything about security............he is unprotected?...............if he gets a virus, trojan or worm..........guess who will get it next?
errrr no he doesn't....................he cuts straight through your corporate firewall or he wouldn't be able to connect.
He does not have any firewall or any of that stuff in place because he sits behind our corporate firewall
All externally connecting machines should have their own firewall and antivirus etc. They are your weakest link, particularly if it is a privately owned home computer, being used by someone without technical knowledge.
As muert0 states quite correctly:
And you need to bring this guy up to speed on security issues, as well as any others like him.
So it's a backdoor to your network with all the passwords written down in plain english for anyone to take and you're playing games instead of doing something about the problem???
I agree, you have much bigger priorities than playing tricks on your colleagues.