Some typos are harmless, others make you want to crawl under your desk and never hit “send” again. In the fast-paced world of work emails, one wrong letter can turn a kind farewell into something… much worse.
From calling your boss a tender nickname on accident to asking a client to do outrageous things, these slip-ups turned ordinary messages into unforgettable jokes.
Mondays are hard enough as it is, but they can always be worse. Here are some hilarious and horrifying work email typos that made a bad day, an awful one.
1
Texted my boss instead of my ex: “Does my little boobear want to hang out this weekend?”
2
My director accidentally typed “facilititties” in an email CC’d to 20 people. You could hear laughter across both floors.
3
I’ve asked clients for a “screenshi*” instead of “screenshot” more times than I’d like to admit.
4
Emailed someone named Dean with “Hi Dead.” He never mentioned it, but coworkers did, and I’m still mortified.
5
Talk-to-text turned “Sorry for your wait!” into “Sorry for your weight!” too many times. I had to stop using it.
6
Signed off an email with “Thanks, Paul [lastname]” but autocorrect changed my last name to “Murderer.” I didn’t catch it until after hitting send.
7
Meant to type “Regards” but signed off with “Retards” instead. Still haunts me.
8
Told a female coworker to “wait a s*x” instead of “sec.” Didn’t live that one down quickly.
9
Tried to tell my boss I’d bring her a moscato. Autocorrect changed it to “miscarriage.”
10
Signed off with: “If you have any questions, please hesitate to reach out.” Sadly, I meant it that day.
11
Tried to text “stuck in traffic” but sent “stuck on toilet” to my boss. I was on my way to a doctor lunch.
12
Got an email asking for info from the “c*nty registry”, they forgot the “o” in county.
13
A rep emailed me that “The shipment is stuck on the d***” instead of “dock.” Still cracks me up.
14
Responded “okay great!” on my BlackBerry, but autocorrect changed it to “okay freak!” Sent it to my boss.
15
Typed our CEO’s name as “Brain” instead of “Brian” on something important. He’s very nerdy, it felt personal.
16
Legendary autocorrect fail: a job applicant ended their cover letter with, “I look forward to sleeping with you soon.”
17
Used ChatGPT to write a message and accidentally included: “Here’s a professional and enthusiastic version you can use.”
18
Meant to write “Salut!” in a bilingual email. Accidentally started with “Sl*t!”
![Signed off an email with “Thanks, Paul [lastname]” but autocorrect changed my last name to “Murderer.” I didn’t catch it until after hitting send.](https://cdn.ebaumsworld.com/2025/08/08/111224/87712534/6.jpeg)
