Caregivers are socializing agents for their children and play an important role in their psychosocial development and desistance from criminal pathways. When children’s psychosocial needs are unmet by their caregivers, social workers play an important role in supporting their healthy development. Considering the increased attention by scholars toward caregiver engagement in children’s interventions, and the acknowledgment of emergent power dynamics in the interaction between caregivers and social workers, it is of interest to explore broader influences of engagement. This paper compares the experiences of social workers and caregivers at an outpatient treatment working on behalf of Swedish Social Services. Caregiver engagement in children’s psychosocial development is discussed from stereotypes and broader sociocultural influences to explore potential power dynamics. The findings suggest that caregiver engagement is not a simple dichotomy of good or bad. Instead, sociocultural influences such as shame, guilt, and blame, along with integrational processes and sociocultural norms are indicative of inclusive and exclusive processes of caregiver engagement. Failure to address intercultural misunderstandings and failure to recognize individual needs beyond the caregiver identity are perceived as discriminatory factors contributing to unfair assessments of caregiver capabilities and practices. Consequently, power dynamics resulting in discriminatory assessments have led to fear and mistrust towards Swedish authorities, leading caregivers to avoid seeking support. This avoidance from caregivers could potentially result in children persisting on criminal or deviant pathways. Therefore, the result warrants awareness of unequal or unjust assessments of caregiver engagement based on prejudice toward cultural and social stereotypes. Practically, this emphasizes the implementation of individualized interventions that promote open communication, trust, and intercultural learning.