Toward the end of the breeding season, migratory songbirds face crucial tradeoffs between the timing of reproduction, molt, and migration. Using stable hydrogen isotopes, we show that male American redstarts investing in high levels of reproduction late in the season adopt a unique strategy of combining molt and migration. Tail feathers molted during migration also reflect less orange-red light, indicating reduced carotenoid concentration. Thus, we show how reproduction in a migratory animal can influence both life history strategies (location of molt) and social signals (feather color) during subsequent periods of the annual cycle.