Some women who initiate breastfeeding will not meet their duration goals. There are a number of factors that contribute to undesired weaning. For a woman who ceases breastfeeding before she desires to do so, it can be devastating. For the lactation professional or peer supporter, this can also feel like failure. The hospice model of grief counseling and ethical principles are applicable to supporting a mother grieving the loss of the breastfeeding relationship she desired. This presentation uses case studies to address the questions of how breastfeeding supporters ethically and compassionately support mothers who end their breastfeeding journey before they wish to, how lactation professionals and peer supporters can manage our own feelings in these situations, and what are the ramifications of these cases as we continue to share accurate breastfeeding information in the face of media-driven culture in which infant feeding is loaded with guilt, shame, and fear.