At Scribophile members can write critiques for people's writing, with comments inserted inline. The underlying software dates back to the PHP5 days when MySQL only had the utf8 option. Everything was working fine for years, when all of a sudden users started complaining that from time to time, they would submit a critique and it would be mysteriously cut off at random places.
The problem was very intermittent, didn't happen very often, and there was no seeming rhyme or reason to it. But when it did happen, it was catastrophic because members would lose hours of work, seemingly at random!
All kinds of testing scaffolding and logging was put in place to try to find the problem with no luck. Then, after quite some time, we realized what the problem was.
At that time, emoji keyboards were brand new; most phones/tablets had limited support, and people didn't yet use phones and tablets for everything like they do now. But they were out there. Some users who were using these new emoji keyboards were inserting emoji smiley faces as they were writing critiques. In Scribophile's web interface, everything looked fine; but when the user submitted the critique, MySQL tried to insert a multibyte Unicode character into a regular utf8 field, and SILENTLY threw that character and all of the data after it away!!
Boy were we upset at MySQL about that one. But at least we figured it out!