Transportation barriers pose significant challenges for individuals involved with the criminal justice system and those with mental and substance use disorders, especially those reentering the community following incarceration. During reentry, returning citizens face a variety of difficulties related to safety, accessing services, and meeting conditions of release, all of which can be exacerbated by insufficient access to transportation. Research indicates that transportation barriers can demonstrably increase a person’s vulnerability to other challenges, such as unemployment, food insecurity, homelessness, and more. People reentering the community from jail or prison often face specific challenges related to transportation, affordability, accessibility, applicability, availability, and awareness. Many individuals do not have the financial means to own a car or regularly use public transportation. Returning citizens may lack appropriate identification to get a driver’s license or may have an infraction, such as a DUI, that keeps them from using a car even if they have one. However, even specialized transportation services can present difficulties, such as a lack of awareness about eligibility, advance scheduling requirements, or constraints only allowing transportation to medical appointments, thus limiting individuals’ ability to use them.