Carotenoid- and phaeomelanin-based sexual pigmentation may signal a capacity to maintain oxidative balance and viability. However, diverse empirical results leave the association between pigmentation and oxidative stress (OS) unclear. We assessed the hypothesis that population-specific levels of oxidative challenge, or strategies for managing OS, affect relationships between sexual pigmentation and OS. Specifically, intense oxidative challenge in migratory, temperate breeding birds might enhance correlations between pigmentation and OS relative to allied tropical breeders, since quality-based differences in OS may arise only under intense oxidative challenge. Alternatively, in temperate breeders with intense within-season reproductive effort, high-quality birds may invest in reproduction over oxidative balance, dampening negative correlations between pigmentation and OS. To assess these alternatives, we compared prenesting relationships between pigmentation and OS in a migratory, Californian population of yellow warblers (Setophaga petechia brewsteri) and in a resident, Mexican population (Setophaga petechia bryanti, "mangrove warblers"). Yellow warblers displayed higher OS than mangrove warblers. However, year of capture and sex had bigger influences on correlations between pigmentation and OS than population. Males with more intense melanin pigmentation had lower OS among mangrove warblers and yellow warblers captured in 2011, but not among yellow warblers captured in 2012. In females only, lower OS levels were associated with more colorful carotenoid pigmentation. Results suggest that both phaeomelanin- and carotenoid-based pigmentation have the potential to correlate with OS levels, but that the signaling potential of pigmentation may shift with inter-annual variation in environmental conditions and display sex-specific dynamics. © 2014 Springer-Verlag Berlin Heidelberg.