“If It Looks Like Its Mum”: 55 Hilarious “Reply All” Work Email Fails

Once I was on a reply all from a company that buys my services that said “I don’t know why we still use him, he’s an idiot”.

I responded “I might be an idiot but at least I know how reply all works”. It went down hill from there.

This guy at my husband's company sent his wife a poem (that he wrote) for their anniversary and accidentally sent it to every single employee in the company (100+ people).

The poem was super sappy, but really sweet. The replies to the email were pretty funny - everybody was pretty nice about it and sent their congratulations on their anniversary. A few people relied along the lines of "Thank you so much for the poem, I love you too xoxoxo".

Not mine but at my partner's place of work they sent out a request for people's Christmas Dinner order. Some guy replied-all to 7,000+ people and requested the full Christmas Dinner and Sticky Toffee Pudding please.

Later in the month when they pushed again for everyone to fill in their choices they added a picture of his face and the comment "Dan Smith has decided his Christmas Dinner order, have you?"

Working in software consultancy, we were delivering a project for a particularly difficult customer called Keith or something.

One day, my boss received a positive email from him, so he quickly forwarded the email to our team saying “wow, Keith is being nice for once”. Only he didn’t forward it onto the team at all, he used Reply All instead.

He tried to do the whole Recall thing when he realised, but we all know that doesn’t really work.

Keith actually found it quite funny, and took it in his stride. His reply was something like:

“I think you might have meant to send this to someone else!

Kind regards,

Wayne Kerr”.

Probably not even going to reach the top end of the most embarrising things and to be fair it didn't really embarrass me, but it did give me a good chuckle.

During covid I was a bit down working from home and being away from my colleagues so I thought id send my team a picture of my dog being dopey with a load of balls around him. Even captioned it 'look at this big dope'

should have been just to my team of 14 people but something went wrong and ended up being @COMPANYWIDE and for about 2 weeks I was getting replies from all over the world saying how cute my dog was.

It got a bit more intense when our Australian CEO replied saying he loved the breed and had his own, too.

I found it slightly cringy since I'm effectively the bottom of the barrel when it comes to the food chain in my company but it didn't seem to piss anyone off.

Instead of attaching a recently completed training, I attached the results of my colonoscopy test and replied all. Not my proudest moment, but at least my test went well.

Someone got a scam email at work with a dodgy link and it messed up their laptop but they helpfully forwarded it to the whole company saying “not sure who this email was supposed to go to but it’s not our department” so about 30 people ended up with bricked laptops. A week later she did it again!

2010-ish, large multinational pharma company.

Fail #1: No limits on email attachment size (managers gotta send those massive powerpoints somehow...)

Fail # 2: User comes back from holiday and attaches 500mb of holiday photos to an email. Proceeds to send email to the entire addressbook (multiple 1000's of recipients)

Fail # 3 and onward: The cascade begins - so many people responded with "Reply to all" (with attachments in tow) just to say "Please remove me from this chain" that the Exchange server went down for days. Each time we resurrected the server more mails came in pushing the same 500mb of attachments to everyone all over again.

Anarchy.

An email from a client asking some questions directed to a new person, and a more experienced colleague replied all (including the client) saying “new employee, client is a real [jerk], she understands nothing and complains about everything, let me read your responses before you send them on to her.”

Not a reply all but instead of sending an mail to their team, someone sent an email to the entire UK distribution list (10,000 people) asking who wanted a cream cake. You can imaging the number of sarcastic replies they got from across the UK.

I may have been one of them asking for a Cream Doughnut. Yummy.

NHS Mail a few years ago. Someone in London was testing a distribution list or something and accidentally copied it to all ~850k users. That started a barrage of "What is this?", "I don't think this is for me!", and the best one "Please stop replying to all as you're copying in people unnecessarily."

It caused absolute pandemonium and completely knacked the NHS internal email system for the entire day, and most of the next day too. Replies were still dropping in hours later. I was working on a service desk at the time so had a deluge of tickets from users asking why NHS Mail wasn't working and helpfully letting us know that they were getting messages from people they didn't know.

It made it onto BBC News.

A woman who worked in Facilities at a company I used to work at, sent an all staff email to say that the back door to the car park was out of action, awaiting repair. Her sister replied to her to say that she doesn’t often use the back door, but would probably make an exception for Damien (a contractor who worked in the warehouse). Obviously, instead of sending it to her sister, she replied all.

Unfortunately for her, the company operates in quite a sociable industry, so I received the email six times, only two of which came from friends still in the company. The other four were from competitors / clients who’d already had it sent on.

We sent an email requesting an 8% reduction on about 1 million pounds worth of business we were outsourcing. Copied into the email was one of our sales guys, who happened to have the same name as one of their engineers.

They accidentally left our sales guy in the response meant for internal eyes only, basically saying " hahah we aren't going to give them any reduction even though we're already ripping them off because they're a bunch of [fools]"

They only realised their mistake when the response got forwarded to our ceo who responded back to them telling them effective immediately all work with said cpanyis to he cancelled and alternative suppliers found.

In the 90's I worked for Dagenham Motors. A newly hired accounts administrator sent emails that included a lot of text language.

One manager replied all with, "What is this [trash]? How much did his parents pay to get him through Uni?!

Owner cc'd the entire company by accident on an email where he was discussing selling the business to a competitor which would have made our entire workforce redundant.

Happened at my workplace. A girl wrote a [spicy] email to a coworker who was her lover, but picked the ALL address instead of his, the whole building got it.

An email went round saying how expenses would now be paid on 15th and last day of the month going forward, and not as soon as claims were processed as it had been previously.

One fairly senior lady (earning at least £70k) replied to all 14,000 employees saying it was unacceptable and how she only had £4.27 left in her account until the end of the month (this was mid month) to buy food and was relying on expenses to eat.

Queue a flurry of attempts to recall the email.

HR sent out an email to the hundreds of employees in the U.K., with a few competition questions to go into a draw for some football tickets. A guy in my building answered all the questions and hit reply all.

Had an email go around about certain happenings along the line (railway) such as [attacks], aggressive people causing issues, threats and so on. Someone replied to the email, which includes all managers, area managers and even managing directors "good thing we have all these security lot going about, useless [jerks]"

Got a load of replies with people just reminding who is part of the group and other just replying wow to which she replied "oh sorry, I was trying to send this to someone else on my own email" which is basically admitting to trying to send confidential information to outside of the company which is very naughty. So yea. There was that.

Not sure if embarrassing, but my favourite was when our second in command retired and the email anniucing his retirement party and how to donate money to a group gift, someone wrote back "hell no, do you know how much more that man makes than I do?!"