Maintaining aircraft within the Air Force remains the key to being mission ready. However, as the fleet continues to age, the average mission-capable rate across the fleet has steadily declined, dipping below 70% in fiscal year 2018, the lowest in six years. The older fleet requires additional inspection and maintenance, and the Air Force has named potential solutions such as less depot-based maintenance and more flight line maintenance, and more condition-based maintenance rather than preventative. There also remains a shortage of experienced maintainers, as the recently closed manning gap resulted in an overabundance of 3-level maintainers and a shortage of 5 and 7 level maintainers. Air Force Secretary Wilson said it herself, “Readiness is first and foremost about training people.” Air Force Training Support Squadrons (TRSS) are tasked with creating this training. This paper is a follow up to previous work in which AR was utilized for content creation of maintenance training (Padron et al., 2019) by detailing the next step in that evaluation, where training content was piloted on the flight line in conjunction with the 367 TRSS and C-5 maintainers out of Travis Air Force Base. Results will be discussed, including best practice recommendations for authoring and use of AR in Air Force flight line training, and analysis of suitability of AR for rapid content creation and advancing maintainer skill proficiency.