A qualitative study involving a follow-up interview with 10 incarcerated and reentry mothers in rural southwest and central Virginia was conducted to explore the influence that women’s close relationships have on their reentry experiences with their families. The Vulnerability Conceptual Model (VCM) was used to sensitize an examination of how incarcerated and reentry mothers negotiate relational vulnerabilities in the context of varying situational vulnerability. Grounded theory analysis revealed three themes that characterized relational vulnerabilities. Given our focus on close relationships and the potential of the VCM to identify opportunities for resilience and vulnerability, we highlighted the influence of ambiguous and ambivalent relationships and unresolved loss and grief due to relationship dissolution or the death of a parent, sibling, child, or intimate partner in the reentry process. The data revealed two types of reentry mothers with divergent trajectories for social reintegration. Implications of these types for therapeutic treatment approaches for reentry women are discussed.