One general aspect includes a method to transmit one or more over-the-air software updates, the method including: (a) receiving, via a controller, a software update; (b) receiving, via a controller, a vehicle command request; (c) in response to the vehicle command request, via the controller, generating a communication package including update callback information based on the software update and a vehicle command based on the vehicle command request; and (d) transmitting, via the controller, the communication package to a vehicle. Other embodiments of this aspect include corresponding computer systems, apparatus, and computer programs recorded on one or more computer storage devices, each configured to perform the actions of the methods.