Each year an estimated 2,000 – 2,500 offenders return to the District of Columbia from prison and roughly 17,000 cycle through the D.C. Department of Corrections. These individuals face a number of challenges upon their return, not the least of which are finding and sustaining adequate housing and meaningful employment. As is known, many offenders disproportionately return to a small number of neighborhoods, which are struggling with high unemployment rates, lack of affordable housing, and strained resources. This is, perhaps, useful for understanding why roughly 2/3rds of returning citizens recidivate upon their return to the community. We find that both locally and nationally, these rates have been fairly consistent over the last several decades. Given these high rates of recidivism coupled with the knowledge that the overwhelming majority of those individuals who are incarcerated eventually get released, the idea of reentry transitional planning becomes ever so important.