Once upon a 6 or 7 years ago...
...I found myself writing a password management wrapper that let people change their LDAP passwords via our website. We had some complexity requirements in place to keep AD happy, with which the LDAP was replicated, so it was the usual "Three out of four character classes, at least eight characters" stuff. To save us from sending things to the LDAP which we knew were going to be rejected, I wrote a few simple tests to check in javascript before the user could submit the form, and update the page with a nice little "Check, check, check" of meeting the complexity requirements.
If you chose to ignore the checks and submit anyway, it would give a "You need..." type message letting you know how close you'd gotten to meeting them. Personally I thought that this was a bit over the top, and the little check marks were probably sufficient, but I was told this was going to be required because users couldn't be trusted... which was sort of hard to argue with.
As a result the error messages got increasingly more terse the more times you pressed the button without meeting the requirements, after 4 or 5 goes it resorted to something along the lines of
"THREE out of FOUR of the following: Upper case letters. Lower case letters. Numbers. Punctuation. Dear god how can you get that wrong this many times?! What the hell are you even doing at $PLACE_OF_WORK with this level of reading comprehension?"
It stayed like that for several months until someone finally noticed and complained and I was forced to change it :(
