Although collaborating with families is essential to the success of students, especially those with disabilities (McConnell & Murawski, 2017; Yell & Bateman, 2020), it is a complicated relationship. It is a relationship bringing together people who care deeply about a child. These relationships can be emotional and include love, compassion, concern, hopes, dreams, and sometimes, frustration, anxiety, and determination. Though each individual wants what is best for the child, those opinions are not always in sync. Teachers are expected to collaborate and communicate with family members. Finding the time and energy to work with not only those families who are eager to work together but also those who appear to lack interest, those who appear overly demanding, and those who are skeptical, resistant, or even at times hostile can be stressful. Collaboration requires both parties to work together toward a common goal (Friend & Cook, 2017). In this article, the authors emphasize how strong relationships between families and teachers can help special educators advocate: (1) with families to share goals; (2) for families to support students; and (3) to families to establish necessary boundaries.