This study examined adult grandchildren’s experience of losing a grandparent in the context of a multigenerational family. Background: Although the death of a grandparent in adulthood is often an expected life event, this loss may still result in grief for adult grandchildren. Furthermore, bereavement is not merely an individual experience, but a family one. Characteristics of the relationship between bereaved adult grandchildren and their bereaved middle-generation parents may influence adult grandchildren’s grief responses. This includes both structural (e.g., gender of parent; coresidence with parent) and emotional (e.g., relationship quality; worry about parent) aspects of this tie. Young adult grandchildren from Wave 2 of the Family Exchanges Study (2013, N = 204) reported on their recent grandparent loss experiences (N = 216) and relationships with their middle-generation parents (N = 142). Three-level multilevel models revealed that (a) grandsons who lost a grandmother reported significantly fewer grief symptoms than all other gender combinations; (b) worry about a middle-generation parent was associated with higher grief symptoms, but; (c) this effect was significantly stronger when the middle-generation parent was a mother, and when adult grandchildren were coresident with that bereaved parent. Finally, relationship quality with the middle-generation parent was not associated with grief symptoms, irrespective of context. Results highlight the intersection of emotional and structural aspects of multigenerational relationships following the death of a family member.