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Abstract: Background: Breast milk is universally acknowledged as the ideal source of nutrition for newborns, offering essential nutrients and immunity. However, despite its benefits, many mothers face barriers to successful breastfeeding. This study aims to explore the limitations and challenges faced by mothers in achieving exclusive breastfeeding (EBF). Aims and Objectives: The primary objective of this study was to identify and assess the challenges hindering successful breastfeeding among mothers. Secondary objectives included exploring confounding factors such as lack of privacy in joint families, employment, medical conditions, and use of galactagogues, as well as issues like mastitis, galactocele, nipple discharge, and chemotherapy. Methods: A prospective study was conducted over 18 months at KEM Hospital, involving 400 mothers. Data was collected through structured interviews and clinical assessments, focusing on maternal health, socio-economic factors, and breastfeeding-related issues. Results: Significant barriers to EBF were identified, including anatomical and nipple issues (e.g., mastitis, galactocele, and nipple morphology problems), health conditions (such as antenatal diseases and utero-placental insufficiency), and psychological factors like postpartum anxiety. Additionally, social factors, including lack of privacy in joint family settings and challenges faced by employed mothers, were associated with lower breastfeeding success. Conclusions: This study highlights the multifactorial nature of challenges to successful breastfeeding, ranging from medical and anatomical conditions to socio-cultural factors and psychological stress. Interventions that address these barriers, such as support for working mothers, medical management of breastfeeding-related conditions, and ensuring privacy for nursing mothers, could significantly improve breastfeeding outcomes. These insights are crucial for developing targeted strategies to promote exclusive breastfeeding and maternal well-being. Keywords: Exclusive breastfeeding, maternal health, breastfeeding challenges, socio-economic factors, postpartum anxiety.