During the COVID-19 pandemic, the “how” and “where” of intergenerational interactions changed. This paper probes this “how” and “where”, focusing on older adults’ (ages 65+) navigation of intergenerational relationships. It draws on a larger mixed-methods study of the experiences of children, teens, and older adults in Canada and the United States during the COVID-19 pandemic. This paper employs an im/mobilities framework to identify the underlying motivations of older adults’ intergenerational interactions, the physical and virtual spaces for such interactions, and the impacts on their lives during COVID-19. Thematic analysis of in-depth interviews and focus groups indicates that during COVID-19, intergenerational relationships were influenced by the digitization of interactions, the selective adherence to public health guidelines, and feelings of fear and missing people. Digital technologies and im/mobility were, independently and aggregately, facilitators and barriers to maintaining intergenerational relationships. The level of compliance to public health directives impacted not only how people connected, but the frequency and place of these interactions; e.g., participants noted moving celebrations, like birthdays, to backyards or parks. Emotions—fear, gratitude, and familial duty—framed older adults’ im/mobility, communication strategies, and relationships with both younger and older generations, with grandparent-grandchild relationships as especially salient. This paper highlights the evolving role of im/mobility and communication methods in intergenerational relationships, and their impacts on older adults’ experiences during disasters.