A system and method of assisting user engagement of vehicle features, the method including: identifying a vehicle engagement feature from a plurality of vehicle engagement features; sending vehicle feature trigger information to a vehicle, the vehicle feature trigger information being information used to detect an occurrence of a vehicle feature trigger that corresponds to the identified vehicle engagement feature; transmitting a vehicle feature engagement notification to a vehicle user of the vehicle, the vehicle feature engagement notification including vehicle feature operating instructions and/or a vehicle feature availability notification; and receiving a vehicle feature usage indicator, the vehicle feature usage indicator indicating that the vehicle user has engaged the identified vehicle engagement feature, wherein the vehicle feature usage indicator is generated by a vehicle system module (VSM) of the vehicle in response to detection of the occurrence of the vehicle feature trigger at the vehicle.