There’s nothing quite like the dread you feel after realizing you’ve sent a questionable email at work. Maybe you notice that the target of your email’s scorn was still CC’d, or maybe you’re a victim of the ever-dangerous accidental-send midway through introducing yourself to a new contact or client. Whatever it is, you’ll never, ever get that email back. That’s the bad news. The good news, though, is that your blunder isn’t anywhere close to as bad as these:

1. Cringe-Worthy Ketchup Correspondence

Generally speaking, you’re most worried about mis-emailing a superior. But bosses make email faux pas, too.

Case in point: British senior legal associate Richard Philips, who, in 2005, became inbox infamous after his secretary spilled ketchup on his suit, and he emailed her to request payment for the dry-cleaning. Requesting payment from a much less well-salaried subordinate would be bad enough, but when you add in that he did so while she was on leave for her mother’s funeral, well… that’s going-viral bad. The email exchange spread across legal circles in the UK and beyond, and Philips eventually ended up quitting, carrying with him a stain far harder to remove than ketchup.

2. Sleazy Sign-Off

There are many different reasons to recommend someone for a raise: stellar client work, potent leadership, innovative cost-cutting. But prowess in the bedroom? Might want to leave that one out.

Apparently British recruitment manager John Cook didn’t get the memo. In response to an email from a co-worker asking why he believed his subordinate deserved a pay raise, Cook listed off reasons like the subordinate’s hard work, her high recruitment rate and, well, their “grrrrrrrrrrrreat” intimate relationship.

Perhaps unsurprisingly, the inappropriate email evoking Austin Powers (or was it Tony the Tiger?) ended up costing Cook his job.

3. The ‘Get Stuffed’ Send

“Reply” versus “Reply all.” It’s just one tiny additional word… but it can mean the difference between continuing to receive a regular paycheck and enduring a shameful public exit.

Just ask Patrick Hazelwood, a school principal whose accidental “reply all” ended up making major news. The email in question? A response to a complaint from an elderly community member, which was forwarded to him by a colleague. His response was probably ill-advised regardless of who it went to, but particularly so when he accidently sent it to the community member herself, instructing his colleague to “tell her to get stuffed.”

4. The CEO Slip-Up

Here’s another one from the Reply-All Hall Of Shame, brought to you by Spirit Airlines CEO Ben Baldanza, who had some explaining to do after accidentally including two unhappy customers on an email mocking their request for a refund.

The customers, Christy and Jim Boswell, had missed a concert because of a three-hour flight delay and their email requesting reimbursement for the cost of the concert somehow made it all the way up the food-chain to Baldanza.

His response, mistakenly sent to the Boswells along with several Spirit employees, included such infuriating phrases as “we owe them nothing” and “let him tell the world how bad we are.” Looks like Baldanza got his wish after all.

5. The Awful Admissions Email

Sending an email to the wrong person at work is bad. But what about sending an email to 28,000 of the wrong people?

The email in question was sent out by the UC San Diego admissions office, telling students “We’re thrilled that you’ve been admitted to UC San Diego.” The only problem: They sent it to all 46,000 applicants, including those who were actually slated for rejection. The heart-broken applicants were emailed an explanation later that night. Hopefully someone checked that send list more carefully.

 

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