In our culture, gender is a deeply felt, value-rich, organizing principle; it informs our understanding of who we are as an individual, as well as who we are supposed to be and how we are supposed to act within relationships. This is especially evident in family relationships, and perhaps most strongly in the relationships of mothers and fathers with their sons and daughters. Thus, when a person comes out as transgender or transsexual, parents often experience a profound sense of loss and confusion about their child's new identity and role in the family. In this article, I discuss parental experiences of grief in response to their transgender child's gender transition and propose that parents who struggle with a child's gender transition may be experiencing ambiguous loss. I discuss these experiences in terms of ambiguous loss theory and introduce the concept of dual ambiguous loss. I also provide clinical suggestions for using an ambiguous loss framework with these parents, and offer directions for future research.