Hi,
I've had incredibly inconsistent (let's call it consistently inconsistent) results with casper remote, VPN and our content management software (we're currently using Bluecoat.) Mostly it has a problem with connecting to the last known ip address of the machine, as a lot of times the JSS sees bluecoats ip address and not the actual IP address of the machine. If both machines are on network in house, it's fine. As soon as the connection has to go through bluecoat it breaks. We've abandoned Casper Remote, If i have to remote to a machine on VPN I use Screen share and the jamf_svc account. Screen share works fine well for us.
Cheers
