The Individuals with Disabilities Education Act of 1990 (reauthorized in 2004 as the Individuals with Disabilities Education Improvement Act) mandates that teachers include parents and guardians as partners in their child's education. Although these partnerships have been shown to help parents and teachers alike, they can also be experienced negatively by both parties, resulting in diminished outcomes for students, stress and frustration for parents, and burnout for teachers. The purpose of this qualitative study was to explore the experiences of teachers of students with disabilities when partnering with their students' parents. After conducting 10 semistructured interviews and using thematic analysis to analyze the data, author identified the following four themes: (1) yearning to be trusted, (2) embracing the paradox ("you can't take it personally"), (3) striving to access empathy, and (4) lacking training and support ("desperate for help"). Findings from this study indicate that teachers desire connection and collaboration with their students' parents but require more professional development and overall support to do so consistently and effectively. The article provides recommendations for specific areas where professional development may be particularly useful in repairing roadblocks to positive teacher and parent collaboration.