Although transportation has been established as a facilitator/barrier to health self-management, little is known about how the context of transportation shapes health self-management behaviors and decision-making among older adults with chronic conditions. This study interviewed 37 older adults with chronic conditions in Florida to examine their perspectives about how transportation influences their chronic care self-management. The data were systematically analyzed for themes. The thematic findings revealed how transportation intersected with participants' everyday experiences with chronic health self-management, how they evaluated transportation as part of the process of making decisions about health, and how creative problem-solving about transportation became an additional health self-management activity for addressing their complex needs. These findings suggest that the context of transportation goes beyond a basic facilitator/barrier for health and enhance our understanding about how transportation services and policies may be changed to better address the needs of older adults with chronic conditions.