15 Worst Autocorrect Mistakes People Have Sent Their Bosses

Using text messages to communicate with your boss is handy, but beware the dreaded autocorrect can make things very awkward.

Since the rise of smartphones communicating via SMS or Short Message Service aka texting has been a fast and convenient way to chat.

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11 Terrible and Hilarious Proofreading Fails

This mode of communication has become so ubiquitous that it’s quite common to set up meetings and communicate with senior management and even clients. But typing a message quickly leaves you susceptible to the equally useful and highly annoying inbuilt autocorrect function on most leading smartphones.

The iPhone autocorrect especially has gained a reputation for making very poor guesses that have led text senders into some very awkward places.

Autocorrect fails never fail to entertain. Here is a list of the 15 worst autocorrect fails sent to bosses.

1. Mind if I pump you later?

There may be nothing worse than accidentally insinuating you’d like to get together with your boss in more than a professional sense. This poor employee got caught in the autocorrect hellhole, not once but three times.

What’s worse is it doesn’t seem like Jaime the boss really had a sense of humor to help their poor employee out of an impossibly embarrassing situation. Good luck autocorrect failure sender, we hope you still have your job.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

2. The job interview

This autocorrect may have cost this poor person their job before they even got the position. While it’s awful to embarrass yourself in front of your boss, at least you have a boss to embarrass yourself in front of.

All the how to get a job guides will tell you to always proofread your resume before sending out, but do they mention text messages?

We hope that recruiters at KPMG could laugh a little and didn’t hold this classic autocorrect mistake against this eager applicant.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

3. Running late

There are just some conversations you don’t want to have with your boss and discussing your body flaws is one of them.

Lucky for this texter their boss seems to see the funny side in accidentally blaming their lateness on their weight issues. Though it might also seem Steven was more than a little excited about this autocorrect failure.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

4. Dead Boss

This text has so many mistakes it is almost impossible to read, but luckily they are almost all side-splittingly funny.

The text gets started with ‘Dead Boss ‘ then escalates to signing off with the gentle ‘kind farts’.

Not only is the text riddled with autocorrect fails it also seems like bad news for its recipient. This clumsy thumbsy looks like they are in for some serious disciplinary action.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

5. Dick Jokes

In this text, the tables have turned and it seems management is having trouble shooting off the right message. D

ick jokes are always a bad idea even more so when all you want to do is make sure the Canadian order gets processed.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

6. SNL takes over autocorrect

Once again the boss here is sending the wrong message to a junior employee. We love his straight-faced reply to the classic SNL joke.

Just how SNL has infiltrated this person autocorrect we aren’t sure but it makes for a winner among the best ‘autocorrect fails of all time’.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect via TheThings

7. Animal Instincts

You’d be lying if you said you hadn’t imagined your boss as an animal at least once. Comparing our managers to animals is a fun lunchtime game but it’s not the thing you want to be sending to them via text.

In this case, it seems ‘Boss Lady’ took the autocorrect mistake to heart and will be off to the gym tonight to shed those walrus-like pounds.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

8.Toilet time

We can’t decide what is funnier, the fact the autocorrect changed traffic to toilet or that Donna obviously has a problem with personal boundaries.

Matt J isn’t surprised by her intimate autocorrect mistake but responds with "Again, TMI Donna.” Showing us that Donan is a classic oversharer.

To Matt J’s credit, he does offer Donna the chance to go home and get better, we wish all bosses were like Matt J.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

9. Lick the box

We urge you to not spend too much time trying to imagine what Mike was thinking when he received this message. But we love his dumbfounded response of just ‘wait what?’.

It is a little sad really that the intended text was as banal as locking a cash box.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect via TheThings

10. Courtroom Drama

Autocorrect fails are embarrassing for many reasons. Not only can they completely change the meaning of words they can infer that you are a little unprofessional and hasty. This autocorrect does all those things and more. Introducing a word into a professional conversation that should definitely never be there. 

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect via TheThings

11. Good Timing

There may be nothing more embarrassing than suggesting sex with your boss or co-worker. Things at work are awkward enough!

We love that the mistake was resoundingly resolved by the last text of an adamant 'six, six, six', just in case the Assistant principal didn't understand what was being suggested.

It's always best to be over the top when fixing autocorrect mistakes, just in case.  

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

12. Step into my Office, Baby

When your boss asks you to go to their office, get over there. But perhaps not with so much haste if this is the message you had received earlier.

This text exchange is really setting the mood for a productive meeting.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

13. Cut to the Bone

This boss doesn't mess around when asking for what they want. Even if what they want and what they ask for may be two very different things.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutoCorrect

14. Client Time

The customer should always take priority. For this poor autocorrect fail, being held up with customer service seems enjoyable.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutocorrect

15. Brief Meeting

This autocorrect fail is one of our favorites because it really doesn't appear to be a mistake. Its request or order seems totally in keeping with this boss' formal demeanor.  Lucky for Janet they were quick to apologize for the error before things got too awkward.

15 Worst Autocorrect Mistakes People Have Sent Their Bosses
Source: DamnYouAutocorrect

Moral of the story? Double check your texts before pressing that send button.