The Ares first stage solid rocket booster is being developed as the primary propulsion system to provide liftoff of the new Ares vehicle from Earth on its way toward low Earth orbit. Since this new five-segment solid rocket booster is heavier and reenters the Earth's atmosphere at a higher velocity than the space shuttle's solid rocket booster, the parachutes for the Ares first stage booster must be larger and stronger than their shuttle counterparts. The drop test program for the space shuttle reusable solid rocket booster recovery system, conducted in the late 1970s, used NASA's Boeing B-52 with the drop test vehicle externally mounted on a wing pylon. This configuration allowed the use of a full-scale mockup of the booster frustum and nose cap for conducting a complete system test. Since this aircraft is no longer available, the suitable alternative for the Ares drop test program is the U.S. Air Force C-17. Limitations on mass and volume on extracted payloads from a C-17, however, present new challenges for the Ares development drop test program. Although the standard operational limit of the C-17 for a single extracted payload is 42,000 pounds, the aircraft is qualified to an upper limit of 60,000 pounds. The Ares test program requires drop masses in excess of 60,000 pounds to adequately test the larger and stronger parachutes. Extracting these heavier loads will require a payload mass envelope expansion of the C-17 aircraft. Details of the process undertaken to expand the C-17 payload mass envelope and information corresponding to the subsequent heavy drop tests of the Ares parachute development program are presented.