Punishment menus allow offenders to choose the punishment to which they will be subjected from a set of options. We present several behaviorally informed rationales for why punishment menus may serve as effective deterrents, notably by causing people to refrain from entering a calculative mindset; reducing their psychological reactance; causing them to reconsider the reputational impacts of punishment; and reducing suspicions about whether the act is enforced for rent-seeking purposes. We argue that punishment menus can outperform the traditional single punishment if these effects can be harnessed properly. Our observations thus constitute a challenge, based on behavioral arguments, to the conventional view that adding (possibly unexercised) punishment options to an existing punishment scheme is unlikely to increase deterrence or welfare. We explain how heterogeneities among individuals can pose problems to designing effective punishment menus and discuss potential solutions. After explaining how punishment menus, if designed and implemented benevolently, can serve socially desirable goals, we caution against their possible misuse by self-interested governments.