Actually this is something that is relevant to my interests.
I prefer to have sudo ask for a password when I'm physically in front of the machine, but not if it's a remote session (e.g. SSH from my laptop to my desktop).
Maybe the SSH agent on the client can re-authenticate to the server when requested?
Note that this is a bad idea from the security standpoint, as it requires SSH agent forwarding. Which means that, if the remote server is compromised, the attacker can use your SSH agent to log into other servers as you.
I prefer to have sudo ask for a password when I'm physically in front of the machine, but not if it's a remote session (e.g. SSH from my laptop to my desktop).
Maybe the SSH agent on the client can re-authenticate to the server when requested?