Recently-released homeless women residing in temporary residential drug treatment programs are at a critical juncture in the process of recovery, transition and reentry. The purpose of this study was to explore factors influencing initial use of drugs and relapse triggers among a sample of incarcerated women exiting jails and prisons, and who are residing in a residential drug treatment (RDT) program and preparing for reentry into their communities. Among this population, relapse to drug use and recidivism are common. A qualitative study was conducted utilizing focus groups to understand the perspectives of formerly incarcerated, currently homeless women residing in a RDT program. Content analysis generated the development of three broad categories: a) factors associated with first drug use; b) factors involved in relapse; c) factors influencing desire to remain drug free. A discussion follows highlighting the importance of targeted interventions at RDT sites that integrate physical, psychological and social needs to optimize reentry into communities. This would include a focus on building self-esteem, life skills, and providing access to resources such as housing, employment, and healthcare.