Transportation is an often-cited barrier to health management, employment, social inclusion, and access to social services. Despite its importance, transportation is largely overlooked in the homelessness literature and, despite their vulnerabilities, persons experiencing homelessness remain largely ignored in transportation research and planning efforts. In an effort to fill these gaps in the extant literature, this study uses life course narratives to explore the impact of transportation dependency, access, and mobility and their influence on homelessness. The research questions explore: (1) What experiences, positive and negative, have older adults experiencing homelessness had with transportation dependency, access, and mobility?; (2) What is the role of transportation dependency, access, and mobility preceding homelessness?, and; (3) What is the role of transportation dependency, access, and mobility in moving from homelessness into housing? Data from the proposed study will examine the implications of transportation dependency, access, and mobility on the well-being of an isolated, vulnerable population of older adults with histories of homelessness in order to optimize transportation systems for individuals, organizations, and communities. Study outcomes will offer implications aimed at improving the mobility of persons at-risk of homelessness and those currently experiencing homelessness, considering transportation as a critical intervention point in the homelessness continuum.