<p>Medicalization has become a key topic in contemporary philosophy of medicine. Discussions about what should be medicalized, what kinds of medicalization are desirable, and how specific cases ought to be evaluated increasingly shape debates about the boundaries and responsibilities of medicine. The medicalization debate is increasingly shaped by pragmatic considerations that draw attention to the complex interactions between mind and body and to the role of social and environmental conditions in shaping health. From this perspective, the value of medical interventions and resources lies in their capacity to contribute to broader goals such as alleviating human suffering and promoting individual and collective well-being. While pragmatic approaches address several shortcomings of stricter, often essentialist frameworks, their existing analytical tools remain limited when it comes to evaluating controversial cases of medicalization. This paper examines these limitations and develops a refined pragmatic framework for distinguishing good from problematic medicalization. Using the case study of the pharmaceutical treatment of behavioral and mood-related symptoms associated with premenstrual syndrome (PMS) and premenstrual dysphoric disorder (PMDD), I propose a two-step approach. This two-step approach acknowledges the complexities of pragmatic medicalization and distinguishes between the potential usefulness of medicines to achieve pragmatic goals and the realization of this potential in actual practice.</p>