... from the button that means, "send this crude joke to the entire company, including the aforementioned boss, and instantly destroy your entire life forever":
Microsoft Outlook is actually full of little landmines like this -- when you type in recipient names, it does that autocomplete thing, so if hypothetically you worked for a publication that starts with a "C," then any time you send an email to anyone whose name also starts with a "C," it immediately tries to autocomplete the recipient to the "Cracked - All" mailing list. Every time. As you know, five of our six most popular contributors are named Chad, so every time I want to reply to one of them with a candid message like "Jack O'Brien? More like Jerome O'Fartmonster!" the email software will try to trick me into sending it to the "Everyone Who Works Here" list.
You might say, "Well, that's what you get for saying mean things about your superiors over email, jackass!" but I, like most people, do most of my interaction with other human beings over some kind of computerized text -- email, instant messenger, text messaging, whatever (in fact, I telecommute to work, so almost all of my interaction with co-workers is done this way). So it's natural to eventually treat email the way you'd treat everyday conversation, including the venting, rumor sharing, and joking that all humans engage in as a necessary part of maintaining our sanity. It's just that now, we're one miniscule twitch of the finger away from broadcasting our ugliest thoughts to the world.
"Oh s**t, oh s**t, oh s**t, oh s**t, oh s**t!"