Systems and methods are described for using a client agent executing on a client to send ICMP messages to an appliance connected via a virtual private network Methods include: establishing, via a client agent executing on a client, a transport layer virtual private network connection with an appliance; intercepting, by the client agent at the network layer, an ICMP request originating from the client; and transmitting, by the client agent via a transport layer connection, the ICMP request to the appliance. Addition methods describe determining, by the appliance, the address identified by the ICMP request corresponds to a second client, the second client also connected via a virtual private network to the remote machine; and transmitting, by the appliance to the second client via the virtual private network connection, the ICMP request. Corresponding systems are also described.