Online higher education is growing at a rapid pace. Although beneficial in many regards, many studies find greater opportunity for student dishonesty. Unethical practices facilitated by e-learning include copying answers, trading solutions, or students taking turns as first mover on assignments to obtain and distribute question details or even solutions to their peers. However, if an incentive structure existed in which a student could be enticed to anonymously betray his or her peers and collaborate with the instructor, it seems reasonable that cheating could be reduced substantially. This framework resembles Prisoner’s Dilemma. The objective of this study is to stylize the Prisoner’s Dilemma game in the digital classroom context and propose instructor applications to set up an effective incentive structure. It is shown that a generous grade lift is a theoretically sufficient incentive to tip students toward defecting from collusion with their peers.