Studies concerning the reintegration challenges of newly released offenders have usually relied on self-report data. The current study capitalized on the perceptions of parole supervisors regarding the challenges offenders face in their first 90 days after release. Participants were 74 Canadian parole supervisors who were randomly selected from the staff and contract community parole offender list in a large western Canadian district. After generating responses to the question concerning the challenges faced by newly released offenders, the responses were edited for clarity and redundancy and were sorted into categories of like statements. Multidimensional scaling pinpointed the statements spatially on a map and cluster analysis grouped the statements on the map into clusters based on conceptual domain. Ten cluster groups emerged from the data: a return to previous behaviors, establishing family support, using old coping strategies, obtaining community support, financial problems, lack of employment experience, stigma, obtaining spiritual guidance, problems with community supervision, and obtaining corrections programming. The findings are largely consistent with other research in this area and suggest that initiatives designed to aid released offenders in community reintegration should take a multidisciplinary approach and involve partnerships between community parole staff and the community. Information about community services should be distributed to newly released offenders. Future research should focus on the perceptions of offenders and other correctional staff. Tables, figures, references, notes