Perceptual anticipation has often been investigated using a video-based, temporal occlusion paradigm, especially in sport. In this paradigm, the participants’ task is to predict the outcome of the situation based only on the information prior to the occlusion. The occlusion point(s) has typically been based on objective, physically-deterministic events (e.g., the point of foot-ball contact in a soccer penalty kick). However, in other dynamic domains (e.g., law enforcement), such events are often less informative with regards to the ultimate outcome of any given action. In this paper, we describe a series of studies that employed a temporal occlusion paradigm in law enforcement. Using a series of converging methods of analysis, the purpose was to identify scenarios that discriminated between experienced and less-experienced law enforcement officers’ ability to accurately anticipate the immediate future state of the situation, and then identify the occlusion point in each discriminating scenario that maximized the experience-based difference. This method can be applied to investigations of perceptual anticipation in other dynamic and complex domains.