A method includes a first wireless device initiating a wireless connection to a second wireless device and monitoring at least one context associated with one of the wireless connection and the second device. When contextual data is received that indicates a condition, the method further includes determining, based on a search of a firmware update service (FUS) database, whether a firmware update for the second wireless device is available within the FUS database. And when an available firmware update is received from the FUS database, the method includes triggering the first device to initiate the firmware update for the second device. The triggering of the first device to initiate the firmware update includes: transmitting a command to place the second device in firmware update mode; and forwarding the firmware update to the second device, such that the first device controls and/or initiates the firmware upgrade of the second device.