The Near Earth Asteroid (NEA) Scout is a deep space CubeSat designed to use an 86 square meter solar sail to navigate to a near earth asteroid called VG 1991. The solar sail deployment mechanism aboard NEA Scout has gone through numerous design cycles and ground tests since its conception in 2014. An engineering development unit (EDU) was constructed in the spring of 2016 and since then, the NEA Scout team has completed numerous ground deployments aiming to mature the deployment system and the ground test methods used to validate that system. Testing a large, non-rigid gossamer system in 1G environments has presented its difficulties to numerous solar sailing programs before, but NEA Scout’s size, sail configuration, and budget has led the team to develop new deployment techniques and uncover new practices while improving their test methods. NEA Scout’s spooled sail and boom design differs from any solar sail design to date: a single square sail membrane spooled upon a non-circular mandrel and the booms are spooled on two separate coils. This configuration was necessitated by the 6U footprint and is not common among other solar sailing missions. The program has planned and completed 3 separate full scale sail deployments to date, with a flight sail deployment test scheduled for FY18. The sail deployment tests have helped mature flight operations plans and developed preliminary off-nominal deployment mitigation strategies. The paper entitled “Design and Development of NEA Scout Solar Sail Deployer Mechanism” was presented at the 43rd Aerospace Mechanisms Symposium. Since then, the system has matured and completed ascent vent, random vibration, boom deployment and sail deployment tests. This paper will discuss the lessons learned and advancements made while working on solar sail testing and redesign cycles.