Successful middle schools exhibit effective practices that engage families as valued partners. However, as at-home learning increasingly shifts to digital spaces, parents may have concerns with technology and how their role shifts in digital learning environments. This includes concerns about the balancing act for parents wishing to encourage students' independent learning, while also providing sufficient structure to make sure students are on-task in digital learning environments. Therefore, this article focuses on effective ways parent and family engagement can support students' autonomous learning through meaningful digital homework, cultivating students' self-regulated learning, and encouraging bi-directional communication that will assist parents as their role evolves in supporting students' at-home learning in online environments.