20 of the Worst (But Funniest) Email Mistakes People Have Made at Work

20 of the Worst (But Funniest) Email Mistakes People Have Made at Work

What’s the worst email you’ve ever sent (accidentally or on purpose) at work?

Have you ever “replied-to-all” by accident? Emailed the person you were badmouthing? Copied the boss in to a sensitive thread?

No wonder we all struggle to press “Send” sometimes!

I would love to be a fly on the wall at some of these offices…

Prepare to feel awkward…

1. “I sent a job application to my (ex)boss! Cringe.”

2. “I sent my boss a slightly risqué photo of myself, wearing a cowboy outfit.”

3. “I sent a really embarrassing, romantic poem to this girl at work via email. Totally on purpose, but she really didn’t take it well. In fact, I got reported to HR.”

4. “I wrote an extremely explicit rant about female staff “making a mess” in the toilets and, instead of sending it to them, sent it to a client.”

5. “I sent my boss a racy email, but accidentally cc’d the entire office into it. His wife works here.”

6. “I accidentally sent ‘I would’ to everyone in my address book. I’m not proud of it.”

7. “One of our clients was called Richard Sprout so we nicknamed him Dick (mature, right?) I may have emailed him instead of a co-worker, saying how well the new name suited him.”

8. “After a few beers, I thought it would be a good idea to email my boss and tell him to go do something bad to himself. I never went back.”

9. “I forwarded an email chain across to my boss – highlighting some info about a project we were completing. Kind of forgot that the earlier emails in the chain consisted of me and a co-worker complaining about how much of an idiot he is. Oops.”

10. “I sent out an angry tirade about my incompetent team members to my boss. I think I actually used the words ‘a disgusting rabble of idiots.’ Didn’t realise I pressed ‘Reply to all.’ Pretty awkward.”

11. “Sent the following to the ENTIRE office: ‘Really sorry I couldn’t make it last night, I’ll make it up to you this weekend though ;)’ My ‘secret’ office romance finished not long after that.

12. “I sent this email: ‘I hope that nasty little dog finally dies so we don’t have to hear about it anymore!’ intended for my colleague, to my boss, about her dog.”

13. “I sent a test email saying ‘TESTTESTBORINGTESTTESTBORING’ to 20,000 database contacts.”

14. “I sent ‘do you mind if I sack him today then?’ to the person I was sacking (instead of my line manager).”

15. “I emailed the boss asking him what he was cooking me for dinner – he has the same name as my husband.”

16. “I once accidentally hit ‘Reply All’ to my entire company – a huge media conglomerate, with thousands of employees across the country – with an email that simply said, “Jeremy Piven.”

17. “I blocked the toilet at work and had to get the HR rep and accountant to help me out. After thanking them for said help, accountant replied to a different thread, with senior managers cc’d in, referencing the incident.”

18. “I accidentally replied to all, complaining about the ‘idiot’ who kept replying to all.”

19. “After the office Christmas party, I found some photos on my phone of a co-worker, with her head down a toilet and her bum pretty much out. I tried to send them to her so we could laugh and cringe together, but accidentally sent them to a client (with the same name) instead.”

20. “I’m an office Junior at a law firm. I wrote: ‘send me that excel billiards game, I’m bored out of my t*ts’ and sent it to everyone in the office.


I think these kind of situations are exactly why Google came up with their “undo send” function (an absolute life-saver, I’d imagine)!

Recruiter Pro Tip

Now obviously, we can learn a lot from these slightly cringe-worthy events…

  • Never reply-to-all. It’s too dangerous! (And kind of annoying).
  • Don’t be nasty via email. (Or just ever for that matter).
  • Explicit messages are best left for text messaging.
  • It’s probably best to always concentrate on what you’re doing at work.
  • Always, always, always (always) check your emails before sending.

Click here to read some more great tips on good email etiquette!

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And here’s where we found them!

If you’d like to read more email nightmare confessions, check out some of our great sources…

Absolutely brilliant.

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