This study investigated how adults over the lifespan flexibly adapt their use of prosocial speech acts when conveying bad news to communicative partners. Experiment 1a (N = 100 Scottish adults aged 18–72 years) assessed whether participants’ use of prosocial speech acts varied according to audience design considerations (i.e., whether or not the recipient of the news was directly affected). Experiment 1b (N = 100 Scottish adults aged 19–70 years) assessed whether participants adjusted for whether the bad news was more or less severe (an index of general knowledge). Younger adults displayed more flexible adaptation to the recipient manipulation, while no age differences were found for severity. These findings are consistent with prior work showing age-related decline in audience design but not in the use of general knowledge during language production. Experiment 2 further probed younger adults (N = 40, Scottish, aged 18–37 years) and older adults’ (N = 40, Scottish, aged 70–89 years) prosocial linguistic behavior by investigating whether health (vs. nonhealth-related) matters would affect responses. While older adults used prosocial speech acts to a greater extent than younger adults, they did not distinguish between conditions. Our results suggest that prosocial linguistic behavior is likely influenced by a combination of differences in audience design and communicative styles at different ages. Collectively, these findings highlight the importance of situating prosocial speech acts within the pragmatics and aging literature, allowing us to uncover the factors modulating prosocial linguistic behavior at different developmental stages.