Drawing on past research and prominent theoretical orientations, this research note suggests new approaches to intergenerational dynamics. For 316 grandparent-grandchild pairs, we found that the transition of grandchildren to higher education, controlling for other transitions, improves the quality of the grandparent-grandchild relationship. For grandparent mentoring, however, we see evidence of a generational stake, with grandparents overestimating their mentoring role, compared to grandchildren, during this transition. This generational stake reflects the importance of grandparent education, with increased mentoring for the college-going grandchildren of college-educated grandparents. These findings indicate that the intergenerational literature can be significantly advanced by taking a long-term perspective, incorporating multiple points of view, and examining contextual variation. Moreover, greater understanding of these intergenerational ties will benefit research on families and individual development.