I have a hyphen in the domain (.com) I use for personal email (it's shorter, just my initial and surname) and I still have had problems in some places with that - it's so frustrating.

I have a .red and a .me and I have never not been able to sign up.

.life has four letters. Lots of terrible attempts to validate email addresses reject TLDs that aren't 2 or 3 characters.

>Lots of terrible attempts to validate email addresses reject TLDs that aren't 2 or 3 characters.

which is sad because .info has been around for 20 years.

pipesandcigars.com let me sign up with a .miami but now I can't login because it says it's invalid. My ISP frantically called me up after starting service because they took all my info down and then the system didn't like the domain. My utility company kept sending me requests to go paperless and I had to call them to get an answer on why that happened since I had accepted the paperless prompt, the issue was the domain.

It's nice to have but I've had quite a few headaches with it