Years ago, I was supporting a network running Secure (now McAfee) Smartfilter, which posted a very prominent block page when keeping the user from accessing a site. It looked like
this (not my screenshot, but similar block page.) The layout of the page is important to note for what happened.
Shortly after 5 PM one day, I get an email from the filter system from a user that was a nice little old lady requesting a very, very raunchy porn website to be unblocked with a request explanation of just "unblock it" (I will not say the site title, but know it was pretty obviously porn from the URL, no possibility of miss-typing a similar site name or clickjacking). I did a double take and proceeded to check the web filter log.
If you look at the screenshot, the first link says "Submit a site review request to your network administrator", which then prompts a box to type why you need it and hit submit. That was how the user requested the site unblock.
The second link on the page is to temporarily override site filtering, which requires a username and password to unblock a site (this login was setup with us for IT only, and would log every attempt that occurred.)
According to the logs, the user didn't even try to override the site filter, but instead decided to take the action that very prominently says "Hey, this is going to go to the guy that maintains the computer network to request an unblock." I was floored that whomever was at the computer trying to surf porn wouldn't even try to override filtering, and clicked through the option to tell IT what they were trying to get to.
Needless to say I ignored the request and went home laughing about it. I found out a few days later that the employees' son was in the office helping her and using the machine at the time. When I say son, he was in his mid 20s, so you really can't say it was just a "kids will be kids" moment.
(EDIT) TL;DR: Employee's 20-something son submitted IT support ticket to unblock porn site on mother's account.