Endometriosis is generally viewed as a gynaecological condition, usually seen in women of reproductive age in whom it causes chronic pelvic pain, often around the time of menstruation, pain during sexual intercourse, and other symptoms. Women often experience a delay of many years in receiving a diagnosis and may be disbelieved when seeking medical care. In this chapter we explore the complexities of women’s experience of endometriosis, which, we argue, are bound up by its contested and gendered nature. The association with menstruation makes endometriosis a stigmatised condition, which further compounds its problematic nature. We situate these issues within the context of women’s experience of living with endometriosis, and conclude with a discussion of attempts to resist the dominant biomedical characterisation through recent developments in endometriosis communities and self-help.