Breastfeeding is not simply a technical or practical task but is part of the transition to motherhood, the relationship between mother and baby and the everyday experience of living with a new baby. Discussion of breastfeeding must therefore include the individual's personal and social context. This paper explores how women in England who have chosen to breastfeed their baby accomplish this task during the early stages of motherhood and the relative weight attached to different factors, which impinge on decision-making. Our findings, based on observing 158 interactions between breastfeeding women and midwives or health visitors from one Primary Care Trust in the north of England, UK, and in-depth interviews with a sample of 22 of these women, illustrate the dynamic between breastfeeding, becoming and being a ‘good mother’ and merging multiple identities as they embrace motherhood. In this context, the value attached to breastfeeding as synonymous with being a ‘good mother’ is questioned. In managing the balance between ensuring a healthy, contented baby and the reality of their daily lives, women negotiate the moral minefield that defines ‘good mothering’ and the diverse conceptions and influences that shape it—including health professionals, their social networks and the wider social and structural context of their lives. The implications for policy and practice are discussed.