Techniques for executing multiple Virtual Private Network (VPN) endpoints associated with an Endpoint Pool Address are disclosed. A VPN endpoint manager determines traffic attributes of traffic addressed to the Endpoint Pool Address. The VPN endpoint manager selects a quantity of VPN endpoints to be executed for processing the traffic based on the traffic attributes. The VPN endpoint manager causes execution of a plurality of VPN endpoints corresponding to the selected quantity. The VPN endpoint manager selects one VPN endpoint, from the VPN endpoint pool, to process each data packet addressed to the Endpoint Pool Address. The VPN endpoint manager may select different VPN endpoints to process data packets of different VPN sessions. The VPN endpoint manager may transfer a VPN session from one VPN endpoint to another VPN endpoint. The VPN endpoints in the VPN endpoint pool operate concurrently to process data packets addressed to the Endpoint Pool Address.