This chapter explores the tensions between what defendants are expected to say and do at sentencing and how their courtroom apologies are understood. Although speech on one’s own behalf has been understood as the sine qua non of self-defense (cf. Green vs. United States (1961)), this chapter considers the ways in which factors including the context of sentencing hearings, the use of formulaic language and the ambiguity of affective indexes (i.e., demeanor evidence) function to limit the remedial potential of defendants’ apologies. More specifically, because the emotional displays required for the performance of remorse can be interpreted in multiple ways, any apology can be used to confirm pre-existing attitudes about different defendants. The chapter draws on the findings of Gruber (2014), a study of 52 apologies delivered during federal sentencing hearings. Whether defendants were speaking on the topic of the offense, their future behavior and/or lessons learned, mitigation of the offense, or the sentence itself, each topic offered its own potential pitfalls for the performance of remorse and acceptance of responsibility that is expected in this context.