Objective: Girls in foster care are 2.5 times more likely to become pregnant in comparison to their peer groups who are not in foster care. Pregnancy and parenting inside of foster care juxtapose the teen’s desire to heal traumas of relational separation and disconnection by creating lasting emotional ties to their child (Boustani et al., 2015), with the absence of familial, supportive relationships that many new mothers ordinarily rely on for support and guidance (Manlove et al., 2011). Research over the last decade has illuminated that this experience is further complicated by the teen’s fear of heightened monitoring and the child welfare system seeing the teen both as a victim in need of protection and as a potential perpetrator of harm (Pryce & Samuels, 2010). Foster care social workers, who teens often fully rely on to ensure that their basic day-to-day, developmental, and relational needs are met, are often also in the position to operationalize and enforce this surveillance as a function of their role and responsibilities. Limited research examines how social workers experience this duality of roles between care provider and professional monitor and what impact that has on the social worker/ client relationship. This dissertation, grounded in Attachment and Relational Cultural Theories seeks to fill this gap by examining ways in which social workers conceptualize, build, and manage relationships with teen parents in foster care while also fulfilling role responsibilities to monitor the teen’s parenting actions. Method: This is a qualitative study that employed a grounded theory methodology. Purposive, non-probability, and snowball sampling strategies were used to recruit licensed Master’s-level social workers who presently or previously provided foster care case management services to teen girls parenting in foster care. Each participant completed two sequential interviews, guided by a semi-structured interview guide developed in collaboration with a senior qualitative methodologist. Interviews were transcribed verbatim, and analyzed using the constant comparison method, that included in vivo and a priori coding to generate thematic and theoretically grounded analysis. To enhance rigor, this researcher engaged in peer debriefing, reflexivity observations, and regular consultation with a senior qualitative methodologist and a content expert to support data analysis. Findings: All participants discussed the importance of authentic connection as a critical component of case management with teen parents raising their children inside of the foster care system. Participants delineated pragmatic agency-assigned responsibilities and relationally driven ways to provide care. Relational aspects of care included how workers took on familial-type roles for their clients, viewed relationships as a safe harbor to engage the client in possibility and growth, used emotional intimacy in developing and maintaining connections to meet their clients where they are. Personally and professionally, to demonstrate healthy foundational relationship qualities, including trust, consistency, predictability, advocacy, authenticity, and genuine care. Participants identified supervision, self-care, and limited population-specific resources as gaps in agency support. Unique to the work with teens parenting in foster care were the pressures of protecting and investing in two generations—the teen parent and the young child, which caused moral and professional distress when the needs of these two generations were in conflict. Discussion and Implications: Participants experienced parenting teens in care as having unique needs, and workers demonstrated both personal and professional commitment to identifying and meeting these needs. Despite systemic deficits and limited structural supports, social workers engaged beyond role expectations and tailored personal and professional boundaries to provide opportunities for their clients to participate in growth-fostering relationships. They identified gaps in supervision, support around self-care and population-specific resources that left workers feeling unsupported and ineffective in providing holistic care for their clients. Social workers identified a significant relational gap in the provision of case management supports and services for teen parents in foster care and addressed the needs by offering teens familial or kinship relationships. Mandated reporting roles and responsibilities may often conflict with social workers’ personal and professional priorities around connection, causing moral distress and requiring workers to be vigilant around protecting the teens’ connections, and to navigate ruptures. Conclusion: Workers identified process- and relationally-oriented supervision, better access to population-specific tangible resources like housing and childcare, and tailored supportive self-care strategies as supports needed to provide relationally grounded care. Future research should incorporate the teen parents’ voice and their lived experiences of social worker/client relationships in foster care through a relational cultural theory framework.