Hilarious (and Disastrous) Emails People Actually Accidentally Sent

Anyone who’s ever clicked "reply all" by accident knows the mortification that the office email system can cause. But regardless of how bad your own email mistakes have been, these stories shared on Reddit are bound to make yours look tame in comparison.

A group of women and men have anonymously shared tales of their worst technological blunders.

From getting their bosses offside, to accidentally trolling their own mothers, these unfortunate souls have learned the hard way to double-check their email correspondence before pressing send:

The one where he emailed everybody’s salaries to their colleagues.

"A colleague of mine (HR Director) once mailed the salaries of all the management levels of the company to all the management," one commenter wrote.

"Ten seconds later he asked us to remove it. We did—after printing it out first, of course. He didn't survive long after that, I can tell you."

The awkward moment where she bad-mouthed somebody to their face.

"When planning a hangout with a bunch of people, I sent a message saying 'I hope X isn't coming' to X instead of my friend," one user confessed.


The time she accidentally told her boss she was leaving.

“I [tried] to send an email to my previous boss asking for a reference for a new job opportunity, but accidentally sent it to my current boss," admitted one commenter.

The one where she sent pornographic material to her teacher.

"I meant to email a finished essay to my English teacher and ended up attaching the wrong, similarly-named Word document," wrote one user. "One was an essay; the other was a graphic fan fiction."

The one where she burned all her bridges at a job.

"I quit my job and left a nasty letter," one user said. "The next day I meant to text a coworker, 'How'd she take it?,' but I accidentally text that to my boss."

The flirty email she sent… to her mom.

"[I sent the message to] my mother. Her name is similar to my boyfriend's was at the time," one user wrote.

The email said: "I just want you so badly. ;)'"

The time he ruined some other guy’s film credit.

“I get wrong emails all the time cause my email is just my name @gmail.com. One time a few months ago it was from guy who had made a film for an architectural school out in LA.

"Apparently some other guy with my name had been in the video and the filmmaker was asking how I wanted my name to appear in the video," one man wrote.

"Well, how could I pass that up? I told him my full name was (First name) Susan Rodriguez (Last Name) Jr. I even went so far as to explain that Susan was an old family name.

"A couple weeks go by, I figure, he probably figured out I am f***ing with him. The he emails the final video to me…"

The guy who got too personal with a client.

“I sent an 'I love you' to my biggest client once," one man confessed. "My significant other thought it was hilarious."

The accidentally sexual company-wide email.

“I was working for a large internet consultancy back in 1999 when you actually had to ship large files on CDs. I was managing a project and was the person who was going to receive the disc,” one man said.

"When I got it, I sent an email to the entire team (around 30 people) asking 'I have the disc in hand, who wants to handle it from here?' But I didn't write ‘disc;’ for some reason, I wrote 'dick'. Needless to say, that email got forwarded to every person in the company."

The time the accusations went flying.

"[I sent] 'I think Josh accidentally killed his dog.' To Josh," one user wrote.

Not subtle.

The way-too-flippant response to a boss.

"One time I heard my young coworker say, 'That's how I roll. Don't hate the playa, hate the game'… Anyway, I thought it was so stupid funny that I decided to text it to my girlfriend for a lol,” one man wrote.

"Unfortunately, my boss was the last person I had sent a text to (my girlfriend was usually the most recent person I'd messaged, so I didn't check twice when I pushed send)," he continued.

"Even better (worse?) was that the last thing I'd said to my boss had been bad news because it was a busy night and I didn't get everything done. So the series of messages read something like: 'Pretty busy night, looks like I won't be getting everything done. That's how I roll. Don't hate the playa, hate the game.'

"I pressed the abort button, like, six hundred times while it was sending but it sent anyway."

Don't hate the playa, hate... email?