Territoriality is a common pattern of space use in animals that has fundamental consequences for ecological processes. In the tropics, all-year resident songbirds usually hold territories throughout the year, whereas most all-year resident temperate species are territorial only during the breeding season. In long-distance migrants, however, the situation is mostly unexplored. Here, we report findings from a Palaearctic–African migrant, the thrush nightingale
Luscinia luscina
. We found that only a fraction of the males was territorial in their East African winter quarters and that this was related to the stage of their song development. Individuals with full song were territorial towards other full songsters, but not towards birds that sang plastic song (i.e. an earlier stage of song development). Plastic singers were not territorial towards full songsters and often settled closely to territorial males. We suggest that territoriality of thrush nightingales in the winter quarters may be a by-product of rising testosterone levels that trigger song crystallization. Collectively, our study indicates that changes in territoriality can occur rapidly, giving rise to shifting proportions of territorial and non-territorial individuals in a population, which may lead to complex dynamics in settlement patterns and resulting ecological interactions.