An understanding of how objective situational features are construed by individuals is essential to uncovering the dynamic process through which the “situation” (e.g., specific work events) interacts with personality in shaping behavior in the workplace. The current study aims to illuminate 1) how personality influences the way employees typically perceive work contexts (i.e., being at work), in general; 2) the role of personality in shaping employee’s unique construal of specific work situations; and 3) the effect of personality-driven situation perception on extra-role behaviors. I used the recently developed CAPTION framework of psychological situational characteristics that define 7 dimensions of situation perception to examine how personality traits influence the perception of being at work, in general. Then, to address Research Question 2, I mapped frequently occurring types of work situations (coded for objective descriptors; e.g., “who,” “when,” “what,” “where”) onto the CAPTION dimensions to investigate whether and how personality traits explain systematic differences in the psychological situational characteristics ascribed to specific types of commonly occurring situations. Finally, to address Research Question 3, I examined how personality-driven situation perception predicted individual differences in work behaviors, specifically personality-relevant behaviors, organizational citizenship behavior, and counterproductive behavior. I then discuss implications for theoretical perspectives that discuss the person-situation effect, as well as insights for how organizations may improve work outcomes through organizational context.