‘Skipped generation’ families, consisting of grandparents and grandchildren with parents absent from the home, are frequently served in social work agencies. These families have unique multigenerational patterns and family structures that are important for service providers to recognize. This paper uses a multigenerational systems perspective to highlight the diversity among grandparent-headed households. Twenty families who were previously part of a larger study of stress, well-being, and life satisfaction among caregiving grandparents constituted a follow-up case study involving videotaped family interviews one year after the first study. Three families representing the range of diversity among the twenty are described with accompanying genograms. Differences in structure, interactional processes, and links with prior generations are identified in each case. These examples reveal the strengths and vulnerabilities, as well as the diversity, of grandparent-headed families.