The NASA Orion Capsule Parachute Assembly System (CPAS) development and qualification testing was completed in September 2018. Over the course of the airdrop and ground testing campaign, the team benefited from the ability to design, test, and adjust the design based on observations and inspection results. While the design team used the best knowledge available and attempted to utilize best practices, a number of lessons were learned that should be documented for consideration by future designers. This paper describes these lessons learned including the use of textile reefing loops, the importance of performing joint tests, the impact of using bight sleeves on parachute deployment, and a surprising number of design changes required in the CPAS system after the decision was made to change the suspension line braid to save system mass.