In parachuting, orthopedic and head injuries are well-documented risks associated with the parachute deployment and landing phases. Thoracic injuries have only been seen on rare occasion in conjunction with direct impact trauma. In this report, we detail a case of a young, healthy, tandem skydiving passenger who suffered bilateral pneumothoraces with delayed symptom onset, with no identifiable injury during the jump or landing. Exploring the forces of the parachute "opening shock," we suggest a plausible compressive mechanism for this novel presentation, as well as briefly discuss the options for diagnosis and conservative management of pneumothorax in the operational context. While this is an exceedingly rare event, pneumothorax should be considered in patients complaining of thoracic symptoms following a skydive.