The SSL VPN session failover solution of the appliance and/or client agent described herein provides an environment for handling IP address assignment and end point re-authorization upon failover. The appliances may be deployed to provide a session failover environment in which a second appliance is a backup to a first appliance when a failover condition is detected, such as failure in operation of the first appliance. The backup appliance takes over responsibility for SSL VPN sessions provided by the first appliance. In the failover environment, the first appliance propagates SSL VPN session information including user IP address assignment and end point authorization information to the backup appliance. The backup appliance maintains this information. Upon detection of failover of the first appliance, the backup appliance activates the transferred SSL VPN session and maintains the user assigned IP addresses. The backup appliance may also re-authorize the client for the transferred SSL VPN session.