Research on transportation and low-income groups has often focused on job accessibility and modeled travel times. Such models disconnect transportation from the more comprehensive social goal of enhancing well-being and fail to account for the full stress and time costs that low-income populations may face. To examine the actual, lived experiences of low-income adults, we conducted 52 interviews in two medium-sized metropolitan areas. Results show that low-income travelers have time costs beyond what is modeled, that low-income populations face stressors, like uncertain and unstable transportation, and that the dynamics of ride giving may strain social relations. In conclusion, we argue that placing transportation within the life experiences of low-income adults is critical for understanding how transportation could support or undermine health and well-being.