Breast/chestfeeding in general can be a fraught topic in the contemporary context in the U.S. and in many other countries, particularly when parents have minimal support either to be able to establish a nursing relationship in the first place or to continue nursing beyond a few weeks. Popular media representations and opinions of breast/chestfeeding in general are often polarizing. Parents and other caregivers who encounter obstacles to producing milk or feeding from their bodies are often made to feel inadequate by public health and media suggestions that “breast is best.” Those who practice extended nursing, on the other hand, are often made to feel that they are damaging their children in terms of physical and psychological/emotional development. Although this ethnography will be focused on extended nursing, it also touches on the challenges and stigmatizing ideas that are associated with breast/chestfeeding in general. In the diverse context of the United States, the experiences of people of different backgrounds are included in the text, as experiences with extended nursing vary by region, family background, gender identity, and different forms of capital to which families have access.