Extended breastfeeding is uncommon and accorded limited research attention in the United States. In this article I analyze in-depth interviews with 66 breastfeeding mothers in Northern California. Mothers reveal their understanding of extended breastfeeding through descriptions of the surveillance of breastfeeding and cautionary tales. I examine the form and content of cautionary tales, emphasizing the pervasive culture of surveillance that underpins their relevance to nursing mothers. I interpret the cautionary tales in light of the dyadic encounter of breastfeeding, maternal identity, and norms about older breastfeeding children. The analysis is relevant to future explorations of early weaning in other regions.