I watched a bunch of it some years ago. Original Stay Night, UBW, Heaven's Feel, Fate Zero and Apocrypha. Read the Fate Zero manga more recently, but that stops halfway through.
Other than that and regularly listening to a cover of OP 2 for Heaven's Feel I really didn't do much since.
Can you ping server 1 from the subnet router?
Make sure to check if you have a firewall blocking ICMP packets on server 1 or somewhere between.
Maybe run traceroute from both serves and compare the route taken and where it stops.
Not really, because the client system is configured to go through the proxy. That proxy will connect to the website and do filtering on the unencrypted content because it is initiating the connection.
Next it'll re-encrypt everything with its own certificate and serve it to the client.
I watched a bunch of it some years ago. Original Stay Night, UBW, Heaven's Feel, Fate Zero and Apocrypha. Read the Fate Zero manga more recently, but that stops halfway through.
Other than that and regularly listening to a cover of OP 2 for Heaven's Feel I really didn't do much since.