This special issue revisits a question our journal has taken up before: what are the possibilities and risks of the doctoral degree in women’s studies? Twenty years after we staged a conversation about how to structure doctoral degree programs in the classic 1998 special issue titled “Disciplining Feminism? The Future of Women’s Studies,” and fifteen years after a 2003 forum on interdisciplinary graduate training, we pause and reflect on the state of the field. The landscape of graduate education in women’s studies has certainly changed—there has been unprecedented growth in new PhD programs—but some of the dilemmas faced by doctoral degree holders remain troublingly familiar. The many short peer-reviewed essays in this issue about the doctoral degree in Women’s, Gender, Sexuality, and Feminist Studies (WGSFS), received in response to our call for papers, are organized along three thematic lines: 1) The job market for WGSFS doctoral degree holders, including the relationship between graduate certificates and doctoral degrees in women’s studies; 2) Curricular and methodological challenges within doctoral degree programs; and 3) Structural challenges faced by WGSFS departments and universities. Our authors range from veteran to midcareer scholars to recipients of PhDs granted in the past decade. Our content includes data-driven analyses and proposals for best practices, as well as a wide array of personal narratives. In addition to our articles on the doctoral degree, we have an article and a short story about the topic of sexual assault and education, an art essay, creative nonfiction, and poetry. We should clarify that throughout this issue, departments are named in varying ways (as women’s studies, WGSS, GWFS, etc.), reflecting the array of naming practices in the field; we deliberately decided against imposing a standard name in view of their freighted meanings.