The exponential increase in the number of women parolees and probationers in the last decade has made women the most rapidly growing group of offenders in the United States. The purpose of this descriptive, qualitative study is to understand the unique gendered experiences of homeless female ex-offenders in the context of healthcare needs, types of health services sought, and gaps in order to help them achieve a smooth transition post prison release. Focus group qualitative methodology was utilized to engage 14 female ex-offenders enrolled in a residential drug treatment program in Southern California. The findings suggested that for homeless female ex-offenders, there are a myriad of healthcare challenges, knowledge deficits, and barriers to moving forward in life, which necessitates strategies to prevent relapse. These findings support the development of gender-sensitive programs for preventing or reducing drug and alcohol use, recidivism, and sexually transmitted infections among this hard-to-reach population.