Unfortunately,hypoglycemia, hyperbilirubinemia, excessive weight loss, and dehydration can sometimes be unwelcome visitors to the start of breastfeeding. These entities can be interconnected, anxiety-provoking, and potentially a breastfeeding deal breaker, leading to supplementation or abandonment of breastfeeding. This quartet has its origins in the early hours and days of breastfeeding relative to hospital policies, skilled support, and careful monitoring of at-risk mothers and infants. This presentation will explore the etiology of these conditions, preventive measures, and suggested interventions. A look at policies, crucial observations, and what mothers and clinicians need to know will be discussed.