Women's incarceration rates have increased dramatically over recent years; with Black women's rates disproportionately and significantly higher than other races. Researchers have attempted to understand this criminal justice involvement disparity, and have suggested two major theoretical pathways Differential Involvement and Differential Selection Theories to explain these racial differences. We use the Differential Involvement Theory as a framework to discuss how the objective experience of economic disadvantage as measured by indicators of structural hardship including educational and employment under-attainment and the experience of psychological stress related to resource loss (because of this disadvantage) may explain women's engagement in criminal activity. In order to conceptualize psychological stress, we used Hobfoll's Conservation of Resource's (COR) Theory and measure. Next, we investigated the link between these factors and the degree (number of times incarcerated, number of months incarcerated in lifetime) of criminal behavior using baseline data collected from a NIH study that drew from a racially diverse sample of former substance abusing, criminally involved urban women. Results indicated potential racial differences in the perception of resource loss, and underscore the complex interaction of the experience of race, poverty, and the unique experience of stress on women's decision making and criminal justice involvement.