This paper considers the flight dynamics and trajectory analysis of a parachute-payload system leaving the C-17 aircraft. The C-17 aircraft considered has an open cargo door, extended flaps and with four turbo-fan engines operating at 2,000ft (Above Ground Level, AGL) and an air speed of 150 knots. Payloads include simplified CONNEX containers with either 192" or 240" lengths, 9ft wide and 5.3ft high. Mass and moments of inertia for these payloads are given. At positive deck angles, these payloads begin to slowly drop from the back of the aircraft due to gravitational forces. For zero-deck-angle aircraft, a ring-slot chute with about 20% geometric porosity is considered to pull the payload at out of the aircraft. Specifically, this study uses the CREATE-AV Kestrel simulation software to model the chute-payload system. The extraction and suspension lines are modelled using a Catenary capability in Kestrel. The extraction line is connected to the (floating) confluence points of CONNEX and chute. The chute and payload will undergo responding-body motions to study the flight dynamics of chutes and payload and to determine the trajectory. Trajectory data will be compared with a payload (no chute and cables) leaving the aircraft at positive deck angles. An adaptive mesh refinement technique is used to better capture the engine exhaust flow and the wake behind C-17, chute and payloads. Friction and ejector forces are estimated for payloads to match the exit velocity and time measured during flight testing. Results show that simulation of extracted payloads follow expected trends seen in the flight tests. Larger the deck angle, longer the distance from the ramp will lead * Research Scientist, USAFA/DFAN. to larger exit velocities which produce smaller payload rotation rates. All payloads begin to rotate clockwise once they leave the ramp. Chute extraction methods leads to much larger exit velocities and shorter exit time. Payload-chute acceleration corresponds to the chute predicted drag in previous studies.