Context shapes negotiators’ actions, including their willingness to act unethically. Focusing on negotiators use of deception, we used a simulated two-party negotiation to test how three contextual variables—regulatory focus, power, and trustworthiness—interacted to shift negotiators’ ethical thresholds. We demonstrated that these three variables interact to either inhibit or activate deception, providing support for an interactionist model of ethical decision-making. Three patterns emerged from our analyses. First, low power inhibited and high power activated deception. Second, promotion-focused negotiators favored sins of omission, whereas prevention-focused negotiators favored sins of commission. Third, low cognition-based trust influenced deception when negotiators experience fit between power and regulatory focus, whereas affect-based trust influenced deception when negotiators experience misfit between these structural context variables. We conclude that regulatory focus primes different moral templates: promotion-focused negotiators’ decision to deceive is determined by moral pragmatism, whereas prevention-focused negotiators’ decision to deceive is determined by opportunism. Because each combination of power and regulatory focus was tied to a specific subcomponent of trust, we further conclude that negotiators engage in motivated information search to determine whether they should deceive their opponents.