I did find out that the location of the final IP address is in San Jose. I didn't know you could use that dig command, thanks.
The linode link says that ping, traceroute and mtr commands use ICMP packets to test and if I'm not wrong Apple's servers don't respond to that (I can't check for this because the VPN blocks ICMP packets too).
I don't know of anything to try. I've just tried ping and traceroute and will try mtr.
Actually this lets you do more than what iTunes lets you. iOS 8.3 has already prevented tools like iFunBox (which also uses this IIRC) to access the app sandbox directory.
The linode link says that ping, traceroute and mtr commands use ICMP packets to test and if I'm not wrong Apple's servers don't respond to that (I can't check for this because the VPN blocks ICMP packets too).
I don't know of anything to try. I've just tried ping and traceroute and will try mtr.