This chapter focuses on the translation of women’s health texts. It presents a historical overview of the women’s health movement and elaborates on its main tenets with regard to health and illness. Particular attention is given to the notions of ‘agency’ and ‘empowerment’. The second part of this chapter addresses critical issues about semiotics, grammar and terminology used in medical texts that address women. It highlights the importance of word choices and connotations, as well as grammatical choices and their implications. The third part of the chapter presents a multiple-case study on translation of texts focusing on women’s health. It discusses two of the most translated women’s health texts: Our Bodies, Ourselves (BWHBC 2011 [1971]), and The Vagina Monologues (Ensler 1998). The chapter discusses the importance and relevance of adaptation in the area of women’s health and focuses particularly on the link between the adaptation process and translator’s agency, as well as the ability of the target text to support women’s agency and their empowerment around health issues.