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, <insert name here>

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 <insert your name here>.

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.”