This paper develops an automated approach to plan for mass tactical airborne operations. This proposed tool enables the user to properly load aircraft according to the mission and user specifications, so that the minimum amount of time is required to seize all assigned objectives. The methodology is based on a hybrid approach in which the first portion is a mathematical model that provides the optimal manifest under “perfect conditions”. This mathematical model is represented by a transportation network, and can be optimized using a transportation algorithm. The optimum solution from the mathematical model is input to a simulation model that introduces the inherent variability induced by wind conditions, drift, aircraft location and speed, and delays between jumper exit times. The simulation returns the expected, best, and worst arrival times to the assigned objectives. This hybrid approach allows a large problem to be solved efficiently with a great deal of time saving.