When I was working for Mid Sussex Times in the 70s an ad in the memoriam section should have read 'To my dear dad.....' it was printed as 'To my dead dad...' It didn't go down well with management and client.
Years ago I played pub football for my local and our goal keeper was married to a woman who had a sister called Heather. Heather was (and probably still is) a big girl. As I mentioned this was several years ago when everyone used to have Nokia mobile phones (you know the sort...ones with snake on). Those Nokia's used to have dreadful predictive text. One Sunday post game we were all sat in the pub and our keeper got a text from his wife and he went to reply "are you with Heather" the Nokia changed Heather to Heavier. He was totally unaware of his faux pas for about 30 seconds when his wife rang up to bollock him for taking the piss out of the size of her sister.
Much hilarity ensued when he got off the phone and told us what he had done.
My late Uncle worked as a manager for East Sussex County Highways. Part of his remit was to send out road marking teams when resurfacing had taken place to repaint the lines on the road. One job was overrunning a bit and he was aware his team wanted to get away sharp on a Friday afternoon, so he paid a visit to them in order to check their work in case they had decided to take a few short cuts to save themselves some time. Upon arrival, everything appeared to be in order until he got to a section of work where some lettering had been applied on the carriageway. In 8 ft capital letters he was greeted with the word "SLOM" instead of "SLOW".
Guess the team did not finish early that afternoon...