Breastfeeding is internationally recognized as the recommended standard for infant nutrition, informed by evidence of its multiple benefits for both mother and baby. In the context of common metabolic conditions such as polycystic ovary syndrome, diabetes (type 1, type 2, and gestational), and obesity, breastfeeding may be particularly beneficial for both mother and infant. However, there is evidence of delayed lactogenesis and reduced breastfeeding rates and duration in women with these conditions, and the effects of altered maternal metabolic environments on breastmilk composition (and potentially infant outcomes) are incompletely understood. In this review, we explore the relationships between maternal metabolic conditions, lactogenesis, breastfeeding, and breastmilk composition. We examine relevant potential mechanisms, including the central role of insulin both in lactogenesis and as a milk-borne hormone. We also describe the bioactive and hormonal components of breastmilk and how these may link maternal and infant health.