Abstract: When people want to conduct a transaction, but doing so would be morally disreputable, they can obfuscate the fact that they are engaging in an exchange while still arranging for a set of transfers that are effectively equivalent to an exchange. Obfuscation through structures such as gift giving and brokerage is pervasive across a wide range of disreputable exchanges, such as bribery and sex work. In this paper, we develop a theoretical account that sheds light on when actors are more versus less likely to obfuscate. Specifically, we report a series of experiments addressing the effect of trust on the decision to engage in obfuscated disreputable exchange. We find that actors obfuscate more often with exchange partners high in loyalty-based trustworthiness, with expected reciprocity and moral discomfort mediating this effect. However, the effect is highly contingent on the type of trust; trust facilitates obfuscation when it is loyalty-based, but this effect flips when trust is ethics-based. Our findings not only offer insights into the important role of relational context in shaping moral understandings and choices about disreputable exchange but also contribute to scholarship on trust by demonstrating that distinct forms of trust can have diametrically opposed effects.