Trust is a central concern when deciding whether to grant a second chance to someone who has acted unethically. Trust involves vulnerability: lowering defenses, sometimes even despite past evidence of misconduct. In the Second Chances Framework, trust is the third factor, inviting reflection on whether the person can be relied upon, the level of oversight required, and whether they exhibit ability, benevolence, and integrity, as outlined in Mayer et al.’s (Academy of Management Review, 20, 709–734, 1995) theory of trust. The chapter illustrates these dynamics through the case of Janet, a manager who violated confidentiality by warning a friend and subordinate about imminent layoffs. Her decision, grounded in compassion, jeopardized trust within the management team. While some may see her benevolence as commendable, doubts about her integrity threaten her standing. Granting Janet a second chance requires assessing whether her lapse was circumstantial or indicative of deeper flaws, and whether colleagues are willing to be vulnerable to her again. The analysis situates trust within broader organizational concerns, showing how breaches increase monitoring costs, reduce collaboration, and endanger team cohesion. Finally, trust interacts with other framework elements—precedent, reparation, transparency, and fairness—highlighting its significant role in second-chance decision-making.