Close home-school communication benefits children, their families, the teacher, and the school community. Throughout the school year, teachers interact with families in a variety of ways, in person and electronically. In this study, the researcher investigated how twenty-two middle and high school urban teachers initiated and maintained communication with students' families. In addition, the researcher analyzed the benefits and challenges of home-school communication. Results of the teacher interviews show the following: (1) teachers communicated with families using a variety of channels; (2) this communication was frequent and early; and (3) this communication did not come without challenges. In addition, the outcomes of this communication were improved student learning and behavior, as well as families becoming teacher's allies.