Low-income people of color are at risk of remaining uninsured due to a variety of factors. This study examined Affordable Care Act (ACA)-related and other health insurance enrollment experiences, observations, navigation needs, and experiences maintaining health insurance coverage among low-income communities of color in an economically disadvantaged community (Metropolitan Detroit). We conducted nine focus groups (n = 87) between May and June 2015. Participants were recruited through community-based organizations serving our key populations of interest. Using an inductive thematic analysis approach, codes and themes were generated. Findings from six themes demonstrated that although health insurance is perceived as important, confusion and frustration persist around health plan benefits and coverage, eligibility requirements and key provisions of the ACA, and enrollment. Individuals face difficulties justifying the cost of health insurance. More focused insurance outreach efforts are needed to achieve the ultimate goal of improving the health of low-income communities of color.