Empirical data has consistently identified insider threat/user error as a leading cause of security breaches in the healthcare industry. To mitigate this, organizations often attempt to invest in technologies and the creation of new processes rather than focusing on more effective and innovative ways of educating and engaging the end users. This quantitative study compares the application of knowledge gained over time when educating healthcare professionals on proper procedures for handling sensitive data through the means of traditional versus gamification style training. The study utilized an experimental approach in order to test four hypotheses that compared the knowledge gained by healthcare professionals when administering different training techniques. The results of this research study suggest that gamification style training tailored toward security awareness could play an essential role in reducing the frequency of internal compromise within the healthcare industry. With the understanding that technology alone will not provide a sufficient safety net for managing human risk, healthcare providers should consider gamification as an option that can improve their cybersecurity infrastructure with minimal cost.