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Prisoner reentry is a well-developed area of inquiry, yet jail inmate reentry remains a largely understudied topic. Little empirical attention has been devoted to jail inmate reentry, and if it is studied, jails are typically grouped together with prisons, blurring the important distinctions between the two. While there are many challenges for jail inmate reentry programming (e.g. high turn over rates, short sentence lengths) jails do offer benefits for reentry that are unique to the jail setting. This paper examines the challenges and opportunities jails provide for reentry, highlighting the importance of reentry within the jail context as well as potential avenues for expanding jail reentry initiatives.