A portable data storage module comprises a control module, a wireless communication module, a rewriteable memory and a data transfer button. When the data transfer button is actuated, the portable data storage module wakes from a sleep mode and the control module initiates a data transfer via the wireless communication module with a device. After the data transfer, the portable data storage module reenters the sleep mode. The portable data storage module may be configured to transfer data, such as a trip plan, between a network host and an in-cab driver communication module. The portable data storage module may also store and maintain additional data, such as a driver log.