Adopted adolescents create identity narratives conceptualizing their connections to their families of adoption and birth. Previous work with a sample of adoptive adolescents identified a sub-group who reported negative experiences regarding adoption as part of their navigating of adoptive identity processes (the "Unsettled" group). The current study examined interviews with adolescents in the "Unsettled" group to elucidate these negative experiences, specifically through identifying the relationship challenges linked to adoption. Participants included 30 adopted adolescents (18 females, 12 males) from a longitudinal study of adoptive families. All the adolescents (M age = 15.2 years) were domestically adopted in infancy by heterosexual couples who were the same race as the adolescents (29 White, 1 Mexican American). Thematic analysis revealed six themes reflecting adolescents' relationship challenges as related to adoption, both in terms of interpersonal interactions and how relational experiences influenced adolescents' thoughts and feelings of past, present, and future selves: (a) Negative experiences in relationships with adoptive family members, (b) Negative experiences in relationships with birth family members, (c) Difficulties in the adoptive kinship network, (d) Negative thoughts and feelings toward the self as an adopted person, (e) Negative views toward adoption as a form of building a family, and (f) Negative connections between adoption and future relationships. Multiple subthemes were also identified that built upon topics within the adoption and family systems literature, such as communication among family members, navigation of birth family contact, and adopted adolescents' perceptions of loss. Also identified were four profiles across themes. Implications for mental health providers and adoption professionals are discussed.