One of several general rules suggested by past work is that it is advantageous to exhibit remorse when one has committed a transgression. A pair of experiments searched for the boundary conditions of this rule. In Experiment 1, mock jurors rated a remorseful defendant as more guilty when the law was fair than when the law was unfair. In contrast, an unremorseful defendant was viewed as equally guilty under both fairness levels. Study 2 conceptually replicated this result, and revealed a 3-way interaction among remorse, status, and gender. It is argued that these findings illustrate the importance of violation of expectations on evaluation and judgment, inside the courtroom and elsewhere.