Previous studies demonstrate the positive effects of parental involvement on student grade point averages (GPAs), standardized tests scores, and other academic outcomes. Because of the positive role of parental involvement on youth academic achievement, many parents and school personnel desire more collaboration between the family and the school. However, obstacles often arise prohibiting such positive interactions, especially for inner-city African American parents. In this study, parents and school personnel at a predominantly African American inner-city high school completed in-depth interviews regarding the barriers to involving parents in their children’s education. Parents and school personnel identified barriers that fit into four descriptive categories: (a) time poverty, (b) lack of access, (c) lack of financial resources, and (d) lack of awareness. Suggestions for decreasing barriers were also discussed. Findings suggest that taking family context into consideration during the planning phases of school-based programs and events improve parental involvement. Implications and recommendations for practitioners are discussed.