Most researchers, policymakers, and educators believe that children do better in school when their parents are involved in their education. However, there is no gold standard for how to engage parents. Consequently, schools often employ a broad range of "parent involvement" efforts, with little clear evidence about what works best and for whom. This issue brief uses data from Chapin Hall's evaluation of the Elev8 full-service schools initiative as an illustrative case study to reflect on the efficacy of different parent engagement approaches during the middle school years. The findings suggest that a small group of parents benefited from school-based parent involvement activities. However, many parents struggled to be present at their children's schools and wrestled with the question of how to motivate their children. The success of parent engagement activities depended heavily on school staff building strong relationships with parents. Based on these findings, the authors present recommendations on how middle schools can effectively involve parents in their children's educations. These strategies include providing parents with information on how to motivate and communicate expectations about learning to their children, fostering individual connections between the school staff and parents, and offering a limited number of easily-accessible programs for parents and families at the school. (Contains 2 footnotes.)