A lot of people either had hardcoded lists, or they checked the length and refused TLDs longer than 3 characters. We kept e-mailing people about it, and kept getting messages back from people who had "fixed" it by adding just us (we'd generally have pointed people to articles listing other new TLDs too, to make it clear to them that this wasn't just one TLD), or increasing the limit to 4 characters... We quickly gave up on trying to get these people to stop having useless checks and settled for just getting them to accept ours.
It's quite shocking people still haven't learnt even after the number of expansions since.
\.[A-Za-z]{2,4}$ (this is the end of the regex in Angular 1.15, it also doesn't support brackets or quotes in the local part, poor showing from Google)
At the time when they were written, gTLDs didn't exist, so the longest a tld could be was 4 characters (.info, .mobi). It's pretty piss poor futureproofing to be honest.