Involvement of parents and family, school personnel, and community members is important because studies from early childhood, elementary, middle, and high schools have shown that students are more successful when their families are actively involved (Gonzalez-Dehass, Willems, & Holbein, 2005, p. 100). One challenge facing K-12 public schools is the development and implementation of systematic and sustainable communication that encourages parents and family members to engage with their students' schools. In this research study, a specific method of communication aimed at establishing communication between schools and grandparents of the school's current students was studied. The Wingman was an e-newsletter that was distributed monthly to grandparents.