The Most Disastrously Awkward Office Emails Ever

The 5 Most Disastrously Awkward Office Emails Ever

Nate Hindman

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 mistakenly 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 accidentally 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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17 Responses to "The 5 Most Disastrously Awkward Office Emails Ever"
    • Roberto Moilien | October 10, 2018 at 9:17 am

      You completed several fine points there. I did a search on the theme and found most folks will have the same opinion with your blog.

    • Gail Hodges | January 31, 2018 at 1:26 pm

      Our letters end with Best regards. I mistakenly sent one that said Best retards. My client called laughing and said she really needed that laugh.

      • Kelli | January 31, 2018 at 3:39 pm


    • Kelli Berry | January 31, 2018 at 11:30 am

      I received a response to an email several years ago that said “I apologize for any incontinence.” I think they meant inconvenience.

      • Elizabeth Larkin | January 31, 2018 at 11:58 am

        That’s the best! -Elizabeth

    • Jill | January 30, 2018 at 11:22 am

      One time I sent a certificate of insurance, that I had manually typed additional insured verbiage on. Instead of relationship I put relationshit. The certificate went to a government office for a client of mine. The person I can been corresponding with noticed the error and asked me to fix it. I was mortified!

      • Elizabeth Larkin | January 30, 2018 at 12:36 pm

        That’s a good one! Elizabeth

    • Tom | November 10, 2017 at 7:07 am

      Auto-correct is what gets me most often.

      After returning from Christmas in Arizona where we stayed at the mothers house of my daughters boyfriend, he had texted me and asked if me and my wife enjoyed our stay during the holidays at their home.

      I replied: Yes, we had a great time and I already Chatted with your mother… Thank you for introducing us!!!

      Problem was, Auto-correct changed the word “Chatted” to “Cheated” without me catching it before I hit send.

      So the reply read: Yes, we had a great time and I already Cheated with your mother… Thank you for introducing us!!!

      His reply 10 minutes later was: ??? Huh ???

      • Elizabeth Larkin | November 10, 2017 at 3:05 pm

        Great story! Elizabeth

    • Dave Nutt | November 8, 2017 at 4:15 pm

      We are a 2 man shop and we do not e mail to get each OTHER ATTENTION JUST TALK

    • John Maier | November 7, 2017 at 4:55 pm

      In the age of immediate content, now more than ever it is necessary to take a moment and review, and again review, the e-mail before sending it. The phrase: Act in haste, repent at leisure is never more true – especially considering the amount of people impacted.

    • Marilyn | November 7, 2017 at 11:46 am

      Good article showing why communiques need to remain professional! Nasty comments, inappropriate comments etc show a problem with the persons thinking processes. Few appreciate that, whether or not the email goes viral, to the wrong person or to all.

    • Chris Strasser | November 7, 2017 at 11:18 am

      What a great collection of articles. I was entertained by the one on bad e-mails. Thank you!

    • Christopher Ridley | November 7, 2017 at 5:11 am

      We’ve all done it, sent an email and in that split second afterwards screamed “Nooooooo!”.
      Whether it was to the wrong person, or just plain stupid.

      I use Gmail now, and it has a handy feature that temporarily delays the email for some seconds after you click send so you can “undo” the sending.

      It has saved my hide several times, though the panic of trying to click on the little “undo” button before it disappears will test one’s motor skills.

      Thanks for a great article

    • Jim Cassedy | November 7, 2017 at 2:15 am

      Thank you

    • Mercedes G Bin | November 7, 2017 at 12:19 am

      Thank you for the invitation!

    • Jacqueline Church | November 6, 2017 at 11:45 pm

      These are sort of run of the mill human error (though cringe-worthy, yes). What I find more intolerable are the ones that show COMPLETE lack of care.

      “Dear [recipient]

      We are so impressed with your writing, we wanted to reach out…”

      Or when I had the old Leather District Gourmet blog…

      “Dear Leather:

      We love your blog and want to …”

      How about CB2 that sent me yesterday a promotional email with a contest link that was broken.

      KitchenAid that sent me a request for feedback that would also enter me in a major appliance giveaway; also, with a broken link.

      Or Travel + Leisure who just sent out a massive email to find their next travel blogger…

      “Could it be your our next blogger?”

      Could it be you’re [sic] editor is asleep at the wheel or you’re writer doesn’t know the difference between your and you’re ?

      From businesses, sending mass emails, (or ANYONE sending a mass email) CHECK ALL SPELLING, GRAMMAR and LINKS.

      Isn’t that basic?

      – and may I never make these mistakes myself (though I probably will)

      Your welcome,

      You’re welcome,

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