Earlier quoted context omitted.
For $5/month you can roll your own OpenVPN server with Digital Ocean and it will. [0] Bonus: your cellular ISP can't see your traffic and you're automatically protected at coffee shops. Downside: Battery life takes a slight hit due to encryption. [0] https://www.digitalocean.com/community/tutorials/how-to-bloc...
For some reason apple blocks access to appleid via Digital Ocean. Have you experienced this?
Perhaps this has happened with DO and Apple have blocked its host address ranges from the API due to unwitting past involvement in hack/DDoS attempts?
This is common with public VPN services that people I know have used. I have the luxury of fixed addressing and decent bandwidth at home, so I run my VPN there and have thus far not noticed any such issues. This also means that services that are location sensitive work as if I'm at home (not some random other place the VPN endpoint appears at).