A system including a vehicle control module configured to control a vehicle system according to an operating plan. The operating plan designates one or more first tractive operations or braking operations to be implemented by the vehicle system along a trip. The system also includes a planning module for generating a transition plan in response to a deviation from the operating plan. The transition plan designates one or more second tractive operations or braking operations to be implemented by the vehicle system as the vehicle system travels toward an approaching location from a second location where the vehicle system deviates from the operating plan. The planning module is further configured to generate a prospective plan in response to the deviation. The prospective plan is configured to be implemented by the vehicle system when the vehicle system at least one of moves past the approaching location or completes the transition plan.