District leaders have invested widely in the creation of parent portals, but have paid less attention to ensuring that they are achieving their purpose in providing information that parents can use in supporting their children's academic success. This study, based on qualitative field note data from a larger four-year study of a continuous improvement initiative focused on improving family engagement during the transition from middle grades to high school, identifies both the challenges families face in using the online parent portal and the challenges school leaders face in: (1) ensuring that the portal is a useful tool to families; and (2) communicating information to families about using the portal effectively. This article suggests the need for district leaders, principals, teachers, and other school staff to reflect systematically on the design and purposes of a parent portal, and ways to make the portal a useful tool for families to monitor students' academic progress and help to improve students' grades. It also provides recommendations for how school leaders can apply a continuous improvement approach to increase the number of families that access the portal regularly.