People are living longer so expectations of grandparents should be redefined. Learning for them should focus on fulfilling family and community roles to retain a sense of purpose. Grandparent education requires a willingness to learn from the observations of younger family members. The intergenerational perceptions of American grandparents were examined to identify conditions for success in a technological environment. The 2,535 non-consanguineous participants were three generations of African-Americans (n = 777), Caucasian-Americans (n = 1,086), and Mexican-Americans (n = 672). Perceptions of the grandparents (n = 1,117), parents (n = 624), and grandchildren (n = 794) were compared within and between the cultures. Each generation completed a separate version of the Grandparent Strengths and Needs Inventory. The six subscales of this instrument assess grandparent Satisfaction, Success, Teaching, Difficulty, Frustration, and Information Needs. All generations and cultures identified favorable aspects of grandparent behavior as well as contexts for further learning. Significant differences were found in observations of grandparent attitudes and behavior across cultures and between generations within cultures. The most significant demographic variable was amount of time a grandparent spent with a grandchild. Lesson themes that represent the uniqueness of cultures and the observations of three generations are recommended as a framework for a differentiated curriculum in grandparent education.