Home-school relationships and communication play an important role in promoting children's and adolescents' development and learning. This study investigated the relations between school-initiated and family-initiated contact regarding school events and concerns regarding adolescents' academic, behavioral, and health issues and adolescents' academic performance and behavioral problems in a Taiwanese context, using a secondary data analysis design. The study included a sample of 13,290 junior high school students in Taiwan, as well as their caregivers and teachers. Unlike the pervasive belief regarding the benefit of parental involvement, this study found that higher levels of overall family-initiated school contact were associated with lower academic performance. The results also suggest that the links between home-school contact and adolescents' academic performance and behavioral problems may be a function of the nature of contact initiated by either the family or the school. Implications for school psychology practice and research are provided.