A trailer backing assistance (TBA) application in a vehicle includes a vehicle attached to a trailer by a movable hitch. The TBA utilizes an HMI, sensors on the vehicle, a GPS system, and a remote computing system (RCS). A controller having a processor, memory, and input/output (I/O) communicates with the sensors, HMI, RCS and GPS via a V2I communications network. The memory stores the TBA which is executed by the processor. The TBA determines conditions have been satisfied, obtains and processes optical data from sensors and RCS, presents a vehicle environment view, prompts a vehicle operator for first and second inputs, calculates a current location of the vehicle, generates a planned path to a target location, presents an animation of the vehicle traversing the path, and continuously displays a live view of the trailer and hitch while actively adjusting on-screen instructions to guide the vehicle and trailer along the path.