Introduction: Many mothers have the goal to breastfeed. However, more than 50% will have breastfeeding difficulty by the 3rd day of life. Mothers who are unable to meet their breastfeeding goals are at higher risk for anxiety, depression, embarrassment, and guilt. Those who stop breastfeeding need support and help resolving these feelings. This case study aims to describe one woman’s difficulty with mental health surrounding breastfeeding, her decision to bottle feed, and her successful transition back to direct breastfeeding. Main Issue: Barriers to the participant’s success with breastfeeding were pre-existing history of depression/anxiety, forceps delivery, uncontrolled perineal pain, infant physical trauma, and nipple/flow confusion. The decision to discontinue direct breastfeeding and start bottle feeding came after 2 months of anxiety, frustration, and persistence. Management: The participant followed her healthcare team’s recommendations of triple feeding, lactation support groups, pediatric chiropractic adjustments, and prescribed galactagogues. After 2 months of exhaustion and deliberation, she made the difficult decision to stop breastfeeding for nutritional benefits and switched to breastfeeding only for her infant’s pleasure and comfort. Lowered expectations allowed the dyad to heal and her son to transition to nearly exclusive breastfeeding at 4 months of life. Conclusion: Clinicians must be aware of the delicate balance between promoting breastfeeding for its nutritional value and health benefits and supporting a struggling mother with mental health needs.