The current study investigates the influence of situational context on perceptions of playful aggression. Using an online data collection instrument embedded with video vignettes showing young boys engaged in aggressive play behaviour, 36 situational profiles that are defined by the unique combinations of variables believed to influence attitudes about playful aggression were created and analysed using the conjunctive analysis of case configurations methods [Miethe, T. D., Hart, T. C., & Regoeczi, W. C. (2008). The conjunctive analysis of case configurations: An exploratory method for discrete multivariate analyses of crime data. "Journal of Quantitative Criminology", 24(2), 227-241]. Educators' perceptions of playful aggression varied considerably, depending on the particular contextual profile that was observed. Significant contextual variability also exists within the groups of profiles perceived by educators' as "most" playful and "least" playful. Policy implications are discussed and recommendations for future research are offered.