This research project seeks to understand why coverage rates (percentage of eligible individuals that are enrolled) for the Special Supplemental Nutrition Program for Women, Infants, and Children, aka the food assistance program WIC, are so low in Illinois— at 41.8 percent in 2017 compared to the national average of 51.1 percent— and what is causing mothers to unenroll or not enroll at all. Using the city of Chicago as a case study for this issue, this paper will describe the barriers to obtaining and maintaining WIC benefits that low-income mothers face under Chicago’s paper colored coupon system that provides a fundamentally different benefits experience to North Side versus South and West Side residents of the city. In particular, this study will uncover the disparities between mothers’ access to WIC and the challenges they face in obtaining and maintaining their benefits. I will elaborate on ways that WIC can improve in the future to be more accessible to mothers, and ways in which the coming transition to an electronic benefits system (EBT) across the country might aid in creating a benefits process that is easier to navigate. Extensive semi-structured interview data is used in this study to highlight both the experiences of those that are directly affected by WIC enrollment, i.e. low-income mothers, as well as the expertise of those who are practitioners and scholars in the field of public benefits. It is concluded that WIC’s time, resource, and safety demands on low-income mothers is a significant barrier to initial and continued enrollment for many, and that the stakes could not be higher for mothers and their children. In order to create a more accessible system, WIC must make efforts to reduce the restrictions around WIC and increase the flexibility of the program to ease the navigation of this complicated public benefits system, already fraught with many bureaucratic barriers.