Academic cheating has become a pervasive practice from primary schools to university. This study aims at investigating this phenomenon through a nomological network which integrates different theoretical frameworks and models, such as trait and social-cognitive theories and models regarding the approaches to learning and contextual/normative environment. Results on a sample of more than 200 Italian university students show that the Amoral Manipulation facet of Machiavellianism, Academic Moral Disengagement, Deep Approach to Learning, and Normative Academic Cheating are significantly associated with Individual Academic Cheating. Moreover, results show a significant latent interaction effect between Normative Academic Cheating and Amoral Manipulation Machiavellianism: “amoral Machiavellians” students are more prone to resort to Academic Cheating in contexts where Academic Cheating is adopted as a practice by their peers, while this effect is not significant in contexts where Academic Cheating is not normative. Results also show that Academic Moral Disengagement and Deep Approach to learning partially mediate the relationship between Amoral Manipulation and Academic Cheating. Practical implications of these results are discussed.