This paper examines variables useful in reconstructing oral (caries, antemortem tooth loss, alveolar defects) and physiological (cribra orbitalia, linear enamel hypoplasia) well-being in two bioarchaeological assemblages from Hokkaido, Japan: Okhotsk (n = 37 individuals) and Jomon (n = 60). Findings are compared and contrasted with each other, with published series from Honshu Japan, and samples from climatically near-equivalent Alaska. It was found that more meaningful comparisons of Hokkaido paleohealth could be made with Alaskan material, rather than the more southerly Jomon. Results were ambiguous with respect to physiological well-being. Low levels of LEH in the cold-adapted samples suggest operating in arctic and subarctic environments with marine-based subsistence regimes is not physiologically expensive. However, the relatively high levels of cribra orbitalia in Hokkaido, relative to Alaska, suggest the picture is not straightforward: the reasons for elevated cribra orbitalia in Hokkaido are unclear. The subarctic and arctic samples formed three broadly similar groupings in terms of oral health profiles: (1) Aleuts and Eskimo; (2) Ipiutak and Tigara; (3) Hokkaido Jomon, Okhotsk, and Kodiak Island. Differences between these groupings could be explained with a combination of sample demographics and subsistence orientations. The extremely high frequency of caries in one sample, caribou hunting Ipiutak, may have been influenced by factors such as low levels of dietary magnesium and potentially cariogenic foodstuffs, such as preparations of caribou stomach contents. It was concluded that oral health profiles are potentially sensitive to differences in subsistence strategies among cold-adapted hunter-gatherers, although they lack predictive value.