A system, apparatus, and method are provided for connecting, configuring and testing new wireless devices and applications. For example, one embodiment of a computer-implemented method for enabling a trial wireless device comprises: automatically pre-provisioning one or more trial SIM cards for operation on a particular wireless cellular network on behalf of a prospective customer; automatically pre-configuring a trial wireless machine-to-machine (“M2M”) device on behalf of the prospective customer; wherein the trial M2M device includes testing and monitoring program code which, when the trial M2M device is connected to a computer system, performs the operations of: automatically connecting to the wireless cellular network execute a plurality of test operations for testing the SIM card and the trial M2M device, the test operations including determining whether the SIM card is correctly provisioned for the wireless network; determining whether the trial M2M wireless device is operating properly; and determining the existence of wireless data connectivity.