An undercarriage clearance system includes a datastore containing undercarriage geometry data including ground clearance data of the undercarriage assembly across a lateral dimension of a wheelbase of the work vehicle; a first sensor configured to collect ground environment data within the vehicle trajectory; and a controller. The controller is configured to: receive the undercarriage geometry data from the datastore; receive the ground environment data from the first sensor; identify an obstacle within the vehicle trajectory; evaluate a height of the identified obstacle and a projected path of the obstacle within the wheelbase of the work vehicle along the vehicle trajectory relative to the undercarriage geometry data to determine an obstacle clearance expectation; and generate an alert command signal based on the determination of the obstacle clearance expectation. A display device is configured to render a display based on the alert command signal representing the obstacle clearance expectation.