Virtual private network (VPN)-related techniques are described. The techniques provide intuitive mechanisms by which a client device more efficiently establishes a VPN connection. In one example, a client device includes a memory, processor(s), and a VPN handler. The VPN handler is configured to monitor actions initiated by one or more applications executable by the programmable processor(s), and determine whether each of the initiated actions requires a VPN connection via which to transmit outbound data traffic corresponding to a respective application of the one or more applications. The VPN handler is further configured to, in response to a detection that at least one initiated action requires the VPN connection via which to transmit the outbound data traffic, automatically establish the VPN connection to couple the client device to an enterprise network, and transmit the outbound data traffic corresponding to the respective application, via the VPN connection.