A system and method for establishing and maintaining an “always-on” data connection to a wireless network through the use of a back off timer and a service check timer is disclosed. The back off timer is initialized to a determined value when a connection is not established. When the timer expires, a connection attempt is made. As further connection attempts are made, the back off timer is set to ever-increasing values. When the data connection is established, the service check timer is initialized. The data connection status is determined at the expiry of the service check timer. When, at the expiry of the service check timer, the data connection is determined to be lost, the connection method is employed.