The invention provides a method and system capable of automatically selecting conditions and parameters (such as scheduled times) for wireless programming of selected mobile devices, and automatically performing wireless programming of those mobile devices using the selected conditions and parameters. A server device examines a history of a selected target mobile device, and in response to that history, predicts a "good" set of conditions and parameters for programming the mobile device. The server device confirms that the mobile device is ready for wireless programming using the selected conditions and parameters (such as the scheduled time), buffers the programming download at the mobile device, and directs the mobile device to inject the programming download into its program memory. The server device is capable of optionally informing a customer associated with the mobile device before or after performing automated wireless programming (or both).