Family engagement in middle school is essential to ensure optimal learning. Middle-level educators (typically Grades 5 or 6 through Grade 8 in the U.S.) play a pivotal role in helping to guide parents' understanding of their evolving roles in supporting their adolescents' academic success. Students particularly benefit from (a) parental support for learning that is developmentally appropriate, and (b) age-appropriate boundaries and positive relationships resulting in the perception that adults in their lives care. These strategies, supported by open lines of communication and effective partnerships between schools and parents, can support the academic success of middle school students and build collective trust between educators and parents. In this article, we provide research-based strategies for middle-level educators to effectively communicate with parents to bolster developmentally appropriate family engagement. These strategies are paired with examples demonstrating how the research translates into practice.