Access to paid time off in the United States is limited compared to most other nations due to lacking federal paid leave policies. Within the labor market access is unequal, with workers with less racial, class, and gender privilege having less access. In the absence of federal policy, most research compares the experiences of those with and without paid time off, building an argument for this important policy. However, research examining the experiences of workers with paid time off who are relatively unlikely to have it is lacking. Applying a critical ecological framework, the current study draws from interviews with 21 single parents working low paying healthcare jobs to extend the literature by examining how they experience workplace paid leave policies. The findings illustrate how the power of a beneficial workplace paid leave policy can be limited by interaction with other workplace policies, policy implementation practices, and the broader social ecology. This interaction transforms this universal policy into a racialized, gendered, and classed policy that can punish low-paid single mothers, who are primarily Black women, for using their earned time for caregiving, thereby contributing to employment instability. The findings of this study add nuance to the available literature and suggests that examining marginalized workers’ experiences of workplace policy implementation can reveal mechanisms by which institutional discrimination is maintained in workplaces.