Under rapidly shifting threat and security response environments, security directors at sports and entertainment venues could greatly benefit from methodologies and tools that can help them make informed decisions on the introduction of new or modified security screening protocols and processes during a planning stage that takes place long before event-day execution. Simulating security processes through simulation software is one such way to test security scenarios before deploying them, in order to gain an understanding of the possible benefits/effectiveness and costs such as patron dissatisfaction or extra manpower or introduction of security vulnerabilities. Randomization is one approach that makes it more difficult for terrorists or other bad actors to minimize the probability of detection. Because of the interest in potentially adding randomization to the patron screening process, simulation is one method that can be used to start to understand how possible randomization initiatives might work for individual venues. We describe three randomization schemes in security screening at sports and entertainment venues, describe the results of simulations testing them, and discuss how security personnel might utilize the results of such simulations.