Authenticating a client to a server accessible through an Internet Protocol Security (IPSec) Virtual Private Network (VPN) appliance. The IPSec VPN appliance and an SSL VPN appliance are configured to receive an initialization command from the client. The SSL VPN appliance is in communication with an authentication appliance for authenticating the client to the server. In response to the initialization command, the authentication appliance generates a client key pair including a client private key and a client public key. The authentication appliance generates a client certificate and a client IPSec profile. The authentication appliance transmits the client key pair, the client certificate and the client IPSec profile to the client. A secure communication session between the client and the server is established. The secure communication session is established through the IPSec VPN appliance. Upon receipt of the IPSec profile, the communication session between the client and the server is encrypted.