The Department of Transportation Office of the Inspector General (2020) investigated the Federal Aviation Administration oversight of Southwest Airlines Safety Management System and noted concerns and gaps in the oversight, specifically with the lack of guidance provided to inspectors in evaluating organizational safety culture. Using the published report as a case study, this work researched different peer-reviewed articles using qualitative and quantitative means to investigate the benefits, limitations, and assumptions of measuring an organizational safety culture. While different methods were used, academia seems to have settled on definitions for safety culture and safety climate with the majority of researchers using survey instruments to collect data. However, commercially available safety culture evaluations seem to use consultant experience instead of academic findings for curriculum and evaluation development. The Federal Aviation Administration could facilitate academic and commercial collaboration to improve guidance to inspectors and resolve gaps in oversight of safety culture in Safety Management Systems.