The maternal process of managing established breastfeeding and, ultimately, weaning the child from the breast was explored using the grounded theory method. Data were analyzed from interview transcripts from mothers, field notes, postal questionnaires from fathers, and individual and discussion group interviews with child health nurses within a Western Australian context. A common social problem emerged for women in the management of their breastfeeding when personal expectations were found to oppose the expectations of others. Being confronted with these incompatible expectations resulted in confusion, self-doubt, and guilt for mothers. These findings are discussed to assist health professionals support breastfeeding mothers.