This study explored community supervision officers’ perceptions of the individual, community, and organizational challenges confronted by program participants after Hurricane María in Puerto Rico and their recommendations for future emergency management. Participants were asked about their perceptions of how the mental health and drug abuse of persons on parole or probation were affected and the measures taken to address these concerns in disaster response. Narratives expose vulnerabilities experienced by those supervised and the aggregated challenges that impact retention in health and rehabilitative services, all of which can detract from successful sentence completion. The disaster response categories call for a more adaptable approach to overseeing procedures in light of the difficulties involved and recognizing the support of the supervised population who have contributed to community initiatives.