In this dissertation I examine the regulation of appropriately gendered bodies within the cycle of care for "female" cancers. In both the cultural imagination and in medical care, activism and treatment of gynecological and breast cancers assume an alignment between individual identity, physical body, and normative ideologies of gender. Throughout, I argue that patients with the "wrong body" for female cancers illustrate the ways in which normative gender expectations are continually (re)produced within medical interactions and contribute to inequality in health care. My analysis draws on the experiences of patients whose bodies and gender identities don't match the medical and social expectations for gynecological and breast cancer care: transgender men who seek out gynecological care, cisgender men diagnosed with breast cancer, and cisgender women with breast cancer and/or BRCA mutations who choose prophylactic bilateral mastectomies. These patients create "gender trouble" for medical professionals. That is, they challenge associations between femininity/ female bodies and masculinity/ male bodies that are taken for granted in social life generally and are naturalized through medical care more specifically. I connect the stories of these patients to show that medical care turns on whether and how an individual "counts" as a man or woman in the context of these interactions and that patient treatment options hinge on their embodied choices. Building on contemporary theories of biopolitics and ethnomethodological theories of gender, I argue that medical interactions are critical to understanding the perpetuation of gender when bodies are under scrutiny. The interview data discussed in this dissertation shows that medical interactions reproduce and legitimate cultural ideologies of gender through patient bodies. Patients both resist and rely on gender ideologies to make sense of their treatment decisions and medical care.