Bad Tech: Greatest email fails

Un-send! Un-send! Oh dear. Best pack your bags, you'll be unemployed in the morning...

Have YOU ever accidentally pressed “send”? Added an attachment you really shouldn't have? Employed “banter” better kept for outside work? Catastrophically misused “Reply all”? Take heart: at least your email fail can't be as bad as this lot…

1. We love ya,

According to AdAge in 2008, Carat Media Agency sent an email to its management detailing the letter to use – complete with “insert name of firee here” sections – when laying off staff. It talked of the importance of saying “right-sizing” rather than downsizing, and advised that if the staff laid off desired, they could of course go home and come back the next day to clear their desk. It was sent to the whole company, shattering with one press of the “send” button the illusion that bosses give a monkeys about .

2. The madness of King McAfee

In July 2009, PC security expert McAfee held a conference at the Sydney Convention Centre attended by around 800 guests. A week later, an email was sent thanking everyone for coming. Hilariously, a spreadsheet was appended that contained the names, numbers, email addresses, employment details and even dietary requirements of more than 1,400 people. Now THAT, Alanis Morisette, is irony.

3. Trousers of shame

In 2005 Richard Phillips, senior associate at law firm Baker & McKenzie, had a jolly little email exchange with secretary Jenny Amner. Despite the apparent gulf between their respective salaries, Phillips sent Amner a mail asking for £4 for removing ketchup she had spilled on his trousers. She replied: “I must apologise for not getting back to you straight away but due to my mother's sudden illness, death and funeral I have had more pressing issues.” She then set about organising a collection for the four quid while the email exchange started making its way to just about every single person who worked in law at the time.

4.“Reply all” sucks

Dan to All: “Just wanted to shoot everyone an email to say you guys really impressed Ed with the presentation yesterday. Great job, keep up the good work”. Claire to All: “Thanks!” Laura to Tammy, All: “If Claire sends one more dumbass 'reply all' like that I swear I'm going to f**king quit.”

5. “I'm not a psycho, honestly…”

When Berkshire's Joseph Dobbie met Kate Winsall at a party he was so smitten he went home and wrote a 481-word email more cringe-worthy than a bad Brucie impression. Among other things, he tells Kate “I will end up giving in to the part of me that never wants to find itself shaking its head and muttering 'if only',” and, “Your smile is the freshest of my special memories. I will keep it with me for moments when I need to find a smile of my own.” Kate sent it to friends and in no time it was all over the media, with the hapless Dobbie even having to go on a date with a Daily Mail journo for a feature – a punishment usually reserved for only the vilest criminals.

6.“…But I have some issues”

Another budding Romeo, “Investment Banker Mike”, was a bit put out when a date didn't reply to his texts. So he wrote a 1,600-word email demanding an apology for leading him on. How had the Jezabel done this? “You played with your hair a lot. A woman playing with her hair is a common sign of flirtation.” Then, Mike laid it on the line: “It would be very convenient for you to date me because we have the same interests… If you don't want to go out again, in my opinion, you would be making… perhaps one of the biggest mistakes in your life.” And they say romance is dead.

7. No velly funny

In 2006, the Treasury apologised for an email forwarded by a junior press officer. Entitled “Advantages of being Chinese”, it came with an attachment that recipients were encouraged to view while “pulling the corners of your eyes as if you were Chinese,” in order to decipher a message reading “No sex causes bad eyes.” The mirth was unbridled among recipients, who included the editors of the Observer and Sunday Telegraph and an associate editor at the Mirror.

8. You've won!!! Oh… Actually, no

In 2009, admissions staff at University of California, San Diego sent a welcome email to 46,000 applicants: “We're thrilled that you've been admitted to UC San Diego,” it trilled. Just one problem: only 18,000 of the 46,000 had actually been accepted. According to the LA Times, the entire admissions staff were subsequently required to be on hand to field angry calls from upset students and parents.

9. “Busy doing jack sh*t”

In 2003, an intern at a prestigious NY law firm sent an email to chums boasting of being, “Busy doing jack sh*t,” a forthcoming “2hr sushi lunch” and his plans to spend “the rest of the day typing emails and bullsh*tting people.” Alas, he accidentally sent it to a mailing list that included 20 partners at the firm. One lengthy, grovelling email later he'd proved that as well as being lazy and arrogant, he was also able to brown-nose to a very high level. So naturally the law firm let him stay.