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Thermoregulatory processes are closely linked to sleep initiation and maintenance throughout the circadian cycle, and may contribute to the increased tendency to nap in older adults. This cross-sectional study examined whether habitual napping in healthy older individuals is associated with altered skin temperature-derived heat-loss dynamics and their relationship with sleep onset. Thirty self-reported habitual nappers and 28 non-nappers (59-82 y) completed a 40-hour multiple-nap protocol under controlled laboratory conditions, with continuous polysomnography and distal-proximal skin temperature gradients (DPG) recordings. DPG was analyzed across scheduled wake episodes and at lights-off preceding each nap opportunity. Habitual nappers exhibited distinct changes in thermoregulatory dynamics compared to non-nappers. Overall, they had a lower DPG during scheduled wakefulness, particularly during the afternoon nap window (14:45-17:30). Their circadian organization of the DPG also differed markedly: they had a higher 24-hour DPG amplitude, a more pronounced 12-hour component, and an earlier DPG phase than the non-nappers. During nap opportunities, shorter sleep onset latency (SOL) was associated with a faster increase in DPG after lights-off in both groups. However, in habitual nappers, sleep onset occurred more rapidly despite a reduced dependence on pre-sleep DPG increase. Together, these findings indicate that habitual napping in older adults is accompanied by altered heat-loss rhythms across the circadian cycle and a reduced coupling between pre-sleep thermoregulatory dynamics and sleep initiation. Circadian-driven thermoregulatory changes may underlie the greater propensity to nap in older adults and differentiate habitual nappers from non-nappers. However, the causal direction of this relationship requires further investigation.