ZDNet has a great list of “classic clueless-user” stories submitted by IT folks.  Here’s one that made me laugh:

4. We currently have a great policy for keeping e-mail to a minimum. It's only kept 90 days, then it's deleted, so if you want to save it past the retention period, you have to put it into a file somehow.

This has been in effect for several years, but amazingly, we had a couple of executives in the legal dept who built up 40,000 messages in their inboxes each, without having any deleted. I finally got the connection when the new "retention policy" was published. The company lawyers who wrote it had a line in the document that excluded themselves from the policy and made sure they could keep everything forever!