Embodiments relate to a system and method of assisting a driver when an item is attached to a vehicle. The method includes identifying an item mechanically coupled to a vehicle, establishing a connection via a communication module, with the item, determining a device, wherein the device is at least one of external to the vehicle, part of the vehicle, and part of the item, establishing communication with the device, and receiving information from the device. The method further includes using the information received from the device to execute a function of the item.