Abstract: System and method for automatically establishing a Virtual Private Network (VPN) link between a mobile device and a VPN server over an unsecure wireless network, comprising, at the mobile device, detecting an attempt to establish a wireless connection to the internet via an unsecure wireless network, probing the unsecure wireless network to determine accessibility over the unsecure wireless network to a VPN server, automatically initializing, based on the determination, a VPN client, the VPN client executed to establishes a VPN link between the mobile device and the VPN server over the unsecure wireless network, directing network traffic of the mobile device through the VPN link and automatically terminating the VPN client when the mobile device disconnects from the unsecure wireless network.