Successful communication is key to health in older age. This is true in the narrow sense of being able to gain critical information e.g., from health care providers, but also more broadly in being able to maintain social ties and pursue meaningful activities, which, in turn, are central to maintaining health and well-being. Compared to younger adults, older adults show both quantitative and qualitative changes in how information is processed and used over time to achieve comprehension. Such systematic age-related neural dissimilarities in processing dynamics and strategies raise fundamental questions about how the human brain supports cross-generational communication, especially in light of accumulating evidence linking interpersonal similarities in brain responses to communicative success. Yet despite its prevalence and tangible health-related importance, naturalistic intergenerational communication involving older adults is understudied. In this paper, we lay out why filling this research gap is critical in advancing our understanding of naturalistic communication, with implications for both science and practice.