The present disclosure provides solutions that may enable an enterprise providing services to a number of clients to determine whether to establish a client based SSL VPN session or a clientless SSL VPN session with a client based on an information associated with the client. An intermediary establishing SSL VPN sessions between clients and servers may receive a request from a client to access a server. The intermediary may identify a session policy based on the request. The session policy may indicate whether to establish a client based SSL VPN session or clientless SSL VPN session with the server. The intermediary may determine, responsive to the policy, to establish a clientless or client based SSL VPN session between the client and the server.