A system and method for automatically configuring a remote computer to establish a VPN connection with a network is disclosed. According to the system and method, a configuration generator determines information necessary for the remote computer to establish the VPN connection, and generate an executable file to be run the remote computer. When run on the remote computer, the executable file automatically updates the remote computer's configuration settings so as to enable it to establish the connection with the network. The information required by the configuration generator can either be extracted from a database automatically, or can be keyed in by a network administrator.