This qualitative study explores the experiences of school professionals working with grandparent-headed families. Twenty individual interviews with an array of professional school staff were conducted. Thematic analysis was utilized, and 3 key themes emerged: (a) compassion for grandparent-headed families' unique challenges; (b) lack of adequate knowledge about grandparent-headed families; and (c) strategies for engaging grandparents raising their grandchildren. Implications address the importance of understanding the unique needs of grandparent-headed families and ways to maximize the success of these marginalized families through active family engagement and school-linked services.