Despite advances in lactation skills and knowledge, insufficient milk production still continues to mystify mothers and lactation consultants alike. Based on 3 cases with similar threads, a connection is proposed between polycystic ovary syndrome (PCOS) and insufficient milk supply. Described are the etiology and possible symptoms of PCOS such as amenorrhea/oligomenorrhea, hirsutism, obesity, infertility, persistent acne, ovarian cysts, elevated triglycerides, and adult-onset diabetes, along with possible pathological interference with mammogenesis, lactogenesis, and galactopoiesis. Clinical suggestions include guidelines for screening mothers and careful monitoring of babies at risk. Further research is necessary to confirm the proposed association and to develop therapies with the potential to improve lactation success.