Youth in foster care face a unique and complex dilemma in juggling relationships with both biological parents and foster caregivers. This study uses a national sample of adolescents in foster care to explore how youths’ perceptions of relationships with both biological parents and foster caregivers influence youths’ emotional and behavioral well-being while in placement. Importantly, this study explores the moderating role of kinship care (i.e., vs. non-kinship foster care) in these associations. Findings showed youth who reported better relationships with foster caregivers were buffered—to varying degrees—against the internalizing-related consequences of poorer perceptions of relationships/interactions with biological mothers. For youth in kinship care specifically, positive perceptions of relationships with foster caregivers almost completely protected youth against internalizing-related consequences of youth perceptions of relationships with biological mothers. In contrast, for all other youth—i.e., those in kinship care who perceived poorer caregiver relationships and for all youth in non-kinship care—youth perceptions of their relationships with biological mothers were significantly associated with internalizing behaviors. Implications for future research and practice are discussed.