Psychoeducation, where clinicians teach problem-solving skills in a supportive environment, can help address families’ social vulnerabilities and promote well-being. Group well-child care (GWCC) may provide unique opportunities for pediatric residents to improve their skills in psychoeducation. Our aim was to characterize pediatric residents’ perspectives and experiences of communication while conducting both individual well-child care and GWCC. We used a longitudinal qualitative study design to conduct 15 semistructured interviews with five pediatric residents who facilitated GWCC. Using the constant comparative method, we characterized pediatric residents’ perspectives and experiences of communication while conducting both individual well-child care and GWCC. Four themes emerged. Residents perceived that GWCC (i) enabled families to honestly share their knowledge and parenting practices, (ii) allowed time and a space for families to share personal stories and scenarios, (iii) facilitated discussions of maternal health and psychosocial matters, toward which residents felt ambivalence, and (iv) fostered skills in psychoeducation that transferred to the rest of their clinical practice. When pediatric residents lead GWCC, they perceive that they can facilitate key aspects of psychoeducation, enabling them to assist families in meeting complex social needs. Residents describe that they transfer psychoeducation skills learned in GWCC to the rest of their practice.