Platooning heavy-duty trucks is a proven method to reduce fuel consumption on flat ground, but a significant portion of the U.S. highway system covers hilly terrain. The effort described in this paper uses experimentally gathered single truck data from a route with hilly terrain and an experimentally-validated two-truck platoon simulation framework to analyze control methods for effective platooning on hilly terrain. Specifically, this effort investigates two platoon control aspects: (1) the lead truck’s vehicle speed control and (2) the platoon’s transmission shifting algorithm. Three different types of lead truck speed control strategies are analyzed using the validated platoon model. Two are commercially available cruise control strategies – conventional constant set speed cruise control (CCC) and flexible set speed cruise control (FCC). The third lead truck speed control strategy was developed by the authors in this paper. It uses look-ahead grade information for an entire route to create an energy-optimal speed profile for the lead truck which is called long-horizon predictive cruise control (LHPCC). Then, a two-truck platoon transmission shifting strategy that coordinates the shift events – Simultaneous Shifting (SS) – is introduced and compared to a commercially available shifting strategy using the validated platoon model. This shifting strategy demonstrates further improvements in the platoon performance by improving the platoon gap control. A summary of these simulations demonstrates that the performance of the platoon can be improved by three methods: adding speed flexibility to the lead truck speed control method, using look-ahead road grade information to generate energy-optimal speed targets for the lead truck, and coordinating the timing of the transmission shifts for each truck in the platoon.