Many business faculties may question why their students cheat. While past research shows that student characteristics predict cheating attitudes and behavior, evidence exists that attributes of classroom contexts also play a part. We investigate how three personality traits (conscientiousness, emotional stability, and openness to experience) and two context variables (classroom culture and pedagogy) affect business students' attitudes toward cheating. Of the personality variables, only conscientiousness directly predicts cheating attitudes, while both context variables show significant relationships. Interactions indicate that conscientiousness, emotional stability, and openness to experience, in combination with context variables, affect some attitudes toward cheating. We recommend actions that might minimize cheating as well as future research directions.