This study looks at the effect of U.S. healthcare policies on the working poor. Following up on previous research that looked at risk factors involved in the take-up rate of insurance, this paper addresses how those risk factors contribute to an individual’s decision to purchase health insurance. The author argues that the working poor are an especially important group to study because they are often too wealthy to afford public insurance, but cannot afford to purchase private insurance carte blanche. Using ethnographic data collected at a small business in Philadelphia, the author concludes that while certain risk factors are significant, more enlightening, the working poor are generally uniformed about health insurance in general. Though being uneducated about healthcare and health insurance is probably not unique to this group, they are most affected by this lack of knowledge because of their precarious position in the U.S. healthcare system.