This article examines the flight dynamics and trajectory analysis of a parachute–payload system deployed from a C-17 aircraft. The aircraft is modeled with an open cargo door, extended flaps, and four turbo-fan engines operating at an altitude of 2000 feet Above Ground Level (AGL) and an airspeed of 150 knots. The payloads consist of simplified CONEX containers measuring either 192 inches or 240 inches in length, 9 feet in width, and 5.3 feet in height, with their mass and moments of inertia specified. At positive deck angles, gravitational forces cause these payloads to begin a gradual descent from the rear of the aircraft. For aircraft at zero deck angle, a ring-slot parachute with approximately 20% geometric porosity is utilized to extract the payload from the aircraft. This study specifically employs the CREATE-AV Kestrel simulation software to model the chute-payload system. The extraction and suspension lines are represented using Kestrel’s Catenary capability, with the extraction line connected to the floating confluence points of the CONEX container and the chute. The chute and payload will experience coupled motion, allowing for an in-depth analysis of the flight dynamics and trajectory of both elements. The trajectory data obtained will be compared to that of a payload (without chute and cables) exiting the aircraft at positive deck angles. An adaptive mesh refinement technique is applied to accurately capture the engine exhaust flow and the wake generated by the C-17, chute, and payloads. Friction and ejector forces are estimated to align the exit velocity and timing with those recorded during flight testing. The results indicate that the simulation of extracted payloads aligns with expected trends observed in flight tests. Notably, higher deck angles result in longer distances from the ramp, leading to increased exit velocities and reduced payload rotation rates. All payloads exhibit clockwise rotation upon leaving the ramp. The parachute extraction method yields significantly higher exit velocities and shorter exit times, while the payload-chute acceleration correlates with the predicted drag of the chute as demonstrated in prior studies.