It’s the beginning of the new millennium, and the company where this pilot fish works decides to start web filtering at one office. Users are resistant, even though miscategorizations and improperly blocked sites have been relatively infrequent, says fish.

One bit of resistance that comes fish’s way is a terse user request to whitelist a website that the content filter is blocking. It’s a law firm’s site, and the software has it flagged for malware.

Fish does a quick check on other malware databases, and the site is flagged on some of them, too. So fish tells user that he’ll have to investigate further before whitelisting the site.

Minutes later, fish gets an email from his boss — cc:’d to his boss’s boss — saying that it’s very important to open up access to this site immediately.

A few minutes after that, fish’s boss’s boss sends fish an email asking why a law firm’s website has been blocked. Fish replies with a long explanation about malware exploits and compromised websites, and reiterates that he has contacted the web-filter vendor for verification.

Fish figures that’s the end of the exchange for the moment. But less than five minutes later, he gets another email from his boss’s boss — and this time it’s cc:’d to everyone involved.

It begins, “I went to that website, and I got a virus.”

Turns out the boss’s boss is working at another location, which didn’t have content-filtering software, fish says. “He clicked the link in the original email and it immediately dropped a drive-by Trojan on his machine, which caused such a flurry of network activity that the network admins at that location came running and told him they had to take his PC off the network.”

The click-happy boss ends his email with the words, “This is a pretty good proof of concept.”

Sharky is looking for a few pretty good true tales of IT life. Send me yours at sharky@computerworld.com. You can also subscribe to the Daily Shark Newsletter.