This thesis defends the central claim that remorse ought to be considered a mitigating factor in sentencing decisions. I advocate a communicative approach to punishment, arguing that it is important that the state attempts to enter into a moral dialogue with those that it punishes and that this requires state actors to be receptive to offender-remorse. I contend that this requires us to accept a weak form of character retributivism and acknowledge that certain limited aspects of an offender's character impact upon their blameworthiness. In making these arguments I look at the nature of remorse and its relationship to apology, alongside the role that remorse currently plays within the courts. I also discuss the role of shame in the courts, the role of mercy in sentencing and argue that there is a correlation between remorse and reduced recidivism.