Steven Tudor defends the mitigation of criminal sentences in cases in which offenders are genuinely remorseful for their crimes. More than this, he takes the principle that such remorse-based sentence reductions are appropriate to be a ‘well-settled legal principle’—so well settled, in fact, that ‘it is among those deep-seated commitments which can serve to test general theories as much as they are tested by them’. However, his account of why remorse should reduce punishment is strongly philosophical in character. He sets to one side the many practical difficulties in implementing such reductions in the real world of criminal justice institutions so that he can focus on the question of whether a plausible account of sentencing can show that remorse should mitigate punishment. I contend that Tudor’s defense of such reductions is unpersuasive in certain respects. Yet even if it can be made more persuasive, I argue that the conditions that would have to be satisfied for remorse-based sentence reductions to be justifiably implemented are so many and various that they would likely exceed our abilities to responsibly grant them in real world legal contexts. I therefore claim that Tudor has failed to provide a defense of the ‘remorse principle’ that serves to explain or justify existing legal practices.