In the Netherlands, punishing repeat offenders is not a foregone conclusion. After a decades-long search for an appropriate punishment, repeat offenders are currently punished by means of a custodial security measure. A custodial security measure is additional incarceration often beyond the original penalty. This new penal measure can be imposed for a maximum of 2 years, and is designed to ensure public safety and reduce recidivism by way of incapacitation. However, given the fact that nearly every repeat offender suffers from severe comorbid problems (e.g., a mental illness and substance abuse disorder), judges tend to consider these objectives from a long-term perspective by insisting on as much treatment during detention as possible. Consequently, the punishment for repeat offenders balances between incapacitation and treatment. While some have argued that the current Dutch sentencing scheme represents a new way of sentencing, this article demonstrates that the reliance on the sometimes dichotomous goals of punishment and rehabilitation is characteristic not only of the current type of repeat offender punishment, but of all previous types as well.