There are over 3 million persons on probation in this country and many struggle with both maintaining recovery from substance use disorders and obtaining secure housing. However, stable housing for those on probation in recovery can potentially reduce relapse and recidivism. We examined recovery housing needs from the perspectives of probation supervisors and clients of Cook County Adult Probation. We administered surveys to probation supervisors and interviewed three clients in recovery as case studies. We learned probation supervisors are in need of further housing training and resources to aid clients in recovery. Clients reported unemployment and a lack of assistance in obtaining affordable housing. We recommend probation departments improve collaboration with housing service providers; obtain training on housing; and utilize recovery housing resources to better serve their clients.