What’s Your Worst Email Gaffe?

What’s Your Worst Email Gaffe?

Whether you hit forward rather than reply, let contact autocomplete steer an important email amiss, or simply forgotten to include a promised attachment, we’ve all made an email mistake or two.

Photo by Ed Yourdon.

Over at Slate, tech writer Michael Agger highlights a few Google Labs features aiming to save us from our email mistakes. We’ve covered them all before, but as a refresher, you should check out previously mentioned Labs features like the Forgotten Attachment Detector, Mail Goggles, and Undo Send—all very cool Gmail additions we can employ in the fight against silly, preventable email mistakes.

NPR saw the Slate article and thought it’d be fun to hear their listener’s worst email blunders, and we can’t help but agree, so why don’t you share your worst email gaffe—and whether or not any of these Gmail Labs features could have helped you out—in the comments.

Can’t Believe I Just Sent That [Slate via NPR]


  • I was sending an email to my boss about a phone line that buggered up or something, i said in the body of the email that we should just get a techo in and i was saying whats happening to the line and stuff, then i went to send it and found out i accidently sent it to the whole office instead of my boss…

    Also when i first started here i had a welcome email from the guy who owns the firm and i called him by his last name instead of his first :S

  • Only a couple of days ago, we got an email asking us to send our payroll person a password to access online payslips. Of course, someone hit Reply to All… not me – I haven’t come up with mine yet!

  • I was a CPL in the RAAF. An email came out from the Unit Orderly Room with a list of people doing a stress management course. None of my troops were on it so I forwarded them the mail with a note along the lines of “Thank God none of you weak hearts is taking part in this pansy crap”.

    One of my slower troops forwarded my mail to the Orderly Room because he “didn’t get on many courses”.

    I left the RAAF as a CPL…

  • My worst email gaffe wasn’t really my gaffe. Quite some time ago I signed up to Shelfari and due to their dubious recruitment methods I sent invites to everyone in my address book. If you know anything about Shelfari you’ll know that they don’t just spam your address list once so people that I’d only ever contacted once or who were business contacts got several emails from ‘me’ inviting them to join.

    As you might guess, I very quickly deleted my Shelfari membership.

  • I had a long email thread going with a work colleague – I was asking him how to sort something out, he suggested I get in touch with a guy (lets call him Mr X). In the email thread my colleague told me Mr X was helpful but sounded slightly retarded on the phone (or words to that effect).

    The thread went on for some time so when I finally came to contacting Mr X I’d forgotten about the negative comments and just forwarded it on! To make things even worse I tried to retract the email – which with exchange is pretty much like saying “Read this email because it’s got some bad sh1t in it”

    Unsurprisingly the guy didn’t take it very well still, nobody got fired… yet.

  • I once was sent a whingy email from a client. I meant to forward the email to a workmate, including my criticism of the client. After clicking send, I realised I had hit reply instead of forward. The client was not happy, haha.

  • An older listener to a radio station I worked for had complained about transmission after running some test equipment as a hobbiest. The office person instead of fowarding the complaint to me CC’d me in response to the gentleman (not usual) so I hit reply and wrote:
    “Thanks, I am sure (techicians) XX and YY will enjoy an afternoon with Mr ZZ in his shed discussing the finer points of Frequency Modulation over cups of tea and chocolate Hob Nobs”

    Luckily he didn’t read it properly to twig my digg but appreciated our quick response.

  • An email was sent to a group of senior managers in my organisation by someone touting for business. The head replied to one of the managers “tell him to f##k off” unfortunately he hit reply to all.

  • The worst example I know of involved two male friends at work (F1 and F2). F1 was the focus of a division wide thankyou email from the female boss, for some work he’d done. In response, F2 sent an email to F1, something along the lines that said boss would obviously like to perform fellatio in thanks on F1.

    F2 then sat and smiled in anticipation at F1’s response. After no reaction for a couple of minutes, F2 called F1, and asked if he’d received the email. F1 checked, no email. F2 checked his sent folder.

    I’ve never seen the blood drain from someone’s face quicker than when F2 realised he’d sent the email to the female boss instead of F1. A closed door meeting with boss soon took place.

    Hilarious really.

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