The 17 Most Cringeworthy “Reply All” Email Mistakes You’ll Ever Read


“Reply All” is a dangerous button. Make the mistake one time and it could cost you your job. We once had a very high-up executive at FOX Sports send a very provocative email about one of our female anchors in the post show notes. She was on the email chain. He was no longer on the email chains thanks to the ol’ HR hook.

Thanks to the internet, the people of Reddit shared some of the worst “reply all” incidents they’ve seen. Grab some popcorn and remind yourself to always check who you’re sending that email to.

From Reddit:

I saw a guy ‘reply all’ with a file attached that included the social security number of his whole family, his income, wife’s income, etc.

Why is this guy sending this out in the first place? Gotta be an uncomfortable dinner that night with the wife. “Hey honey I may have leaked your SSN and income to everyone at work. This meatloaf is very dry.”

HR manager sent an Excel workbook with some pertinent info on the first sheet to everyone, but failed to remove the fourth sheet which had everybody’s salary.

So is the wage gap real? We need to know. Can’t just leave us hanging like that bud.

There was an email floating around the office about some sort of event that someone was trying to organize. I can’t remember exactly what it was about, but this woman clearly thought she was only responding to her friend when she wrote, “I’ll tell you the coochy cream story later.”

100 percent that every man in the office was trying to be friends with her after that.

There’s this woman here at work. Almost every time when the CEO sends an email to all staff announcing something new or good she replies to all, telling the CEO how good he is and how much she admires his work and dedication to make our company better. And just how much Jesus has blessed him and everyone working here.

A few minutes later she replies to all again apologizing for that ‘mistake’ because that was intended just for him.

Could her nose be any browner?

Worked on a TV show that everyone except the creator hated, and everyone knew from the ratings would be canceled any second. I was working in legal, and on an email chain where a report of outstanding legal issues for the upcoming episode was sent to literally everyone you could think of (50+ people) ranging from me (one title above entry level) to the head of the network.

A middling executive replied to all “they’re getting canceled and we still have to deal with this shit?”

To make matters worse, she attempted to RECALL the email, just drawing more attention to it, and then replied to all again “PLEASE DISREGARD LAST EMAIL, TRYING TO GENERATE AN INTERNAL REPORT FOR [MY DEPARTMENT], HIT THE WRONG BUTTON”
It was the “Hit the wrong button” that sent me and my boss into hysterics. I so badly wanted to reply that we didn’t know there was a shit-talk button.’

Rule number one in “reply all” disaster control is to distance yourself from the email chain as fast as possible. Pray that no one saw it.

My former coworker hit reply-all on an email about a golf scramble. He tried forwarding it to another guy talking about seeing one of the new interns in a short golfing skirt.

Wait… you let the interns go too?

After an all-staff announcement (around 2000 people) from the new CEO about an upcoming downsizing, one person replied to everyone shortly after saying:

“Can you believe this shit Kate? This new CEO is such a fucking cunt, I swear if I see him on the street I’ll break his fucking neck”

As you can imagine, that’s threats of violence and taken pretty seriously. On the plus side though, she didn’t have to stress about the downsizing anymore because she was fired.

Guy seems like a real straight shooter.

Got one at work where the sender addressed her frustration with “these people” which, in context, meant black people. About 30 of the 150 or so recipients were black.

Welp, that’s one way to get fired.

I worked for a delivery company, and someone sent an email about something very unimportant and CCed pretty much everyone in the company, 99% of whom had nothing to do with the subject. At least once a day for the next two weeks, someone would hit “Reply All” and everyone would get another unimportant email.

Finally, someone freaked out and sent this email to everyone about how hitting reply all was costing the company money because it had to send the email to so many people. Everyone at that company was pretty technology illiterate and I found it highly amusing.

That is vintage old person technology logic right there.

Founder asking “how to fire the outsourced Indian developers” cc’ed to the outsourced Indian developers. Problem solved itself quickly.

At least they are very cheap to replace.

My first job out of school, my manager had to fire someone. The manager was pretty young, and it’s the first time he ever had to do this. He sends an email to HR for assistance and direction as to how to go about firing this person.

Well, the issue became moot when he accidentally CC’d the guy who was going to be fired. We were able to actually see the moment that guy got the email…though we didn’t know what happened at the time. But we did see him stand up and storm over to the manager’s office.

Well executed. Just subtle enough where you don’t feel bad doing it face-to-face, but direct enough to get the point across.

Company-wide email about the use of proper language on the floor – there had been a few cases of people swearing in front of clients, etc.

Guy responds “fuck that” or something similar, thinking he was forwarding it to a friend to discuss the situation.
…he was let go twenty minutes later.

All 20 of those minutes were spent praying that no one important saw his mistake.

Fortune five hundred company. Email blast to many many departments and a VP of important things replied all:
“It is Saturday night and I am too drunk to respond to these emails!”

That’s a VP that people want to work for, but who’s the nerd sending out emails on a Saturday night.

Company sent out an email to all employees asking them to sign and return their employment contracts (complete with comp plans) before a certain date.

Just about everyone understood this meant in a separate email. But a few did it as a reply all, and showed over 2000 employees what their comp was.

Do people not realize what the “all” stands for in “reply all”?

I was included in an email with a few other managers inquiring about an issue with a client. One of the managers hit ‘Reply to All’ but forgot to take me off her reply before it was sent. As soon as I read it, I knew her reply was not meant for me to see. Her entire email was her criticizing my work. Everyone just acted like nothing happened 🙁

There is no such thing as bad criticism in my book. Which is why I tell Duda his outfit is horrendous every day.

My cousin once sent an email meant for his girlfriend to everyone in his address book. He wrote in great detail about the ways in which he and his brothers English bulldog were going to have sex with her when he got home. This probably happened 15 years ago, and I’m sure he has convinced himself that everyone has forgotten. Things like that stay forever.

While not dealing with the workplace, this is still an unfortunate email mishap. Now everyone knows that you and your girlfriend like to violate an animal. Shame on you.

Worked at a large Fortune 100 company (~70k employees) a few years back. CEO sent out an email to “All Users”, then some fuckstick replies all with a comment back. The chain reaction of dimwits all clicking Reply All to say “Stop pressing reply all” brought the email system to its knees for about 5 days.

It’s a never-ending hell and if you’re the dick who keeps it up, just know everyone hopes you get fired.

[via Reddit]

Image via Shutterstock

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Harrison Lee

Harrison is a Content Manager at Grandex. When he's not working for the man, you can find him on the golf course or blowing his paycheck doubling down on red. LinkedIn profile

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