People’s behavior is characterized by stable if…then… profiles, or if in x situation then behavior a, but if in y situation then behavior b. But how do researchers conceptualize and measure if…then… profiles? Drawing from Cognitive-Affective Processing System (CAPS) theory, we discuss recent developments in assessing if…then… profiles, and how such profiles can provide a window for elucidating key aspects of the underlying personality system. Specifically, the Highly-Repeated Within-Person (HRWP) approach assesses how a behavior varies as a function of key features in a situation, and operationalizes if…then… profiles as regression betas. We illustrate how the HRWP approach can be applied to data from often-used social cognitive tasks, wherein an individual is exposed to a large number of situations that differ on a dimension that has been experimentally-manipulated by the researcher, and their behaviors to the situations are tracked. The HRWP approach allows researchers to more precisely assess a given individual’s if…then… pattern, make stronger causal inferences about a given individual’s personality system, and empirically investigate, rather than simply assume, if there are meaningful differences between individuals in the causal processes.