PURPOSE OF REVIEW: This review examines the complex relationship between gestational diabetes mellitus (GDM) and breastfeeding outcomes, integrating recent evidence on maternal health benefits, milk composition, and clinical support strategies. Understanding these relationships is important as GDM affects approximately 14% of pregnancies worldwide, with rates continuing to rise alongside increasing obesity and maternal age. RECENT FINDINGS: Women who breastfeed for longer periods after GDM show significant improvements in metabolic health, including reduced weight retention and better cardiometabolic profiles. While macronutrient content of breast milk appears preserved, significant differences exist in human milk oligosaccharides and milk fat globule membrane proteins. A previous history of predominant breastfeeding shows a 47% reduction in abnormal fasting glucose odds in subsequent pregnancies. Initial positive indications of personalized support programs, particularly during pregnancy, are emerging however evaluation in comparison to current evidence-based interventions is yet to be carried out. Lifestyle factors are known to reduce subsequent diabetes after a GDM and recent evidence suggests these are important in pregnancy and may improve breastfeeding outcomes. SUMMARY: Despite the challenges of delayed secretory activation and reduced milk supply in women with GDM, successful breastfeeding offers substantial health benefits. Healthcare providers could implement comprehensive, individualized support strategies beginning in pregnancy and extending through the postpartum period to optimize outcomes for both mother and infant.