Have you had issues with the .jhw TLD on Apple devices? I have my own DNS for my homelab with CoreDNS with house.hill as my domain. My house is on a hill. But .hill is not a TLD, and both my macbook and iphone stopped resolving it quite a while ago.

No. Both MacOS and iOS happily resolve and connect to the machines in my homelab.jhw domain. I did add the root cert of my CA (Certificate Authority) to the trust store on MacOS and iOS, so I can also enjoy TLS connections. Scroll to the "Add the certificate" part of https://jan.wildeboer.net/2025/08/Create-SMIME-Cert-stepca/ for the HOWTO that worked for me.

If you have Advanced Tracking and Fingerprinting Protection enabled for Safari, it will ignore your system resolver. iCloud Private Relay also ignores it unless DNS is set using configuration profiles.

That generally suggests they’re not pointing at the resolver you have set to handle that domain. Otherwise your apple devices can’t tell a valid TLD from an invalid one: they just launch the DNS lookup and let the server tell them.

The exception to this is .local, which you shouldn’t use for internal systems because it will confuse the heck out of them in weird ways, because .local is by RFC not meant to be used in that way.