Single-mother students on welfare are a small, unique demographic in institutions of higher education. My preliminary research shows, more often then not, that social service caseworkers use discretion to impede, rather than support single-mother students in pursuit of higher education. In my Interdisciplinary Studies Field Major (ISF) thesis project, I will conduct a qualitative study of the academic trajectory of single mothers (SMs) on welfare who pursue higher education by transferring from community colleges to universities in California and Hawai’i. My research question is: How are single-mothers supported or discouraged throughout their experiences as students and welfare recipients? By critically assessing the Welfare Reform Act of 1996 as the legal framing of the contemporary “welfare to workfare” ideology, I will investigate how implementations of this statutory law create bureaucratic controlling processes and moralist state gatekeepers, as well as facilitates the need for advocacy organizations to enable success for SM students. The significance of this project ethnographically illustrates: (1) the historic defederalization of the welfare system, (2) the feminization of poverty, and (3) ethos of discretionary practices.