Background: Women with upstream social determinants of health, particularly those with recent experiences of incarceration, homelessness, and/or substance use, encounter a series of barriers in accessing health care services and consequently face poor sexual and reproductive health outcomes. Driven by a community concern for increasing rates of syphilis and congenital syphilis among women who are structurally disadvantaged, this study focuses on their experiences with reproductive healthcare access across healthcare settings.Research Design and Study Sample: This community-basedpláticas(conversational) research project gathered 12 in-depth interviews andtestimonios(testimonies) with women who reported a criminalized upstream barrier (incarceration, homelessness, and/or substance use) in a small city in the southwestern U.S.-most of whom identified as Latina/Hispanic.Analysis and Results: Using a grounded analysis and drawing upon Chicana feminist methodologies, this study identifies four major themes: (1) homelessness and economic vulnerabilities, (2) incarceration and health care, (3) drug use, provider stigma, and motherhood, and (4) desired changes to the healthcare experience.Conclusion: Results highlight the need for economic and transportation supports, community-based preventive services as alternatives to incarcerated healthcare, along with more compassionate and structurally competent provider-patient dialogue.