This study investigates how adults over the lifespan flexibly adapt their use of prosocial speech acts when conveying bad news to communicative partners. Experiment 1a assessed whether participants’ (N=100 ages 18-72) use of prosocial speech acts varied according to audience design considerations (i.e., whether or not the recipient was directly affected by the news). Experiment 1b assessed whether participants (N=100 ages 19-70) adjusted for whether the news was more or less severe (an index of real-world knowledge). Younger adults displayed more flexible adaptation to the recipient manipulation, while no age differences were found forseverity. These findings are consistent with prior work showing age-related decline in linguistic perspective-taking but not real-world knowledge. Experiment 2 further probed younger (N=40 ages 18-37) and older adults’ (N=40 ages 70-89) prosocial linguistic behavior by investigating whether real-world knowledge relating to older adults’ life experiences (i.e., health-related matters vs all else) would affect responses. While older adults used prosocial speech acts to a greater extent than younger adults in this context, they did not distinguish between conditions. Our results suggest that the use of prosocial speech acts is partially context- dependent and may vary due to differences in perspective-taking, life circumstances, and communicative strategies at different ages. Collectively, these findings highlight the importance of situating prosocial speech acts within the pragmatics and ageing literature, allowing us to better understand which contextual factors modulate prosocial linguistic behavior at different developmental stages.