Studies of sexual signalling generally focus on interactions between dyadic pairs, yet communication in natural populations often occurs in the context of complex social networks. The ability to survey social environments and adjust signal production appropriately should be a critical component of success in these systems, but has rarely been documented empirically. Here, we used autonomous recording devices to identify 118 472 songs produced by 26 male common yellowthroats (Geothlypis trichas) over two breeding seasons, coupled with detailed surveys of social conditions on each territory. We found strong evidence that common yellowthroat males adjusted their total song production in response to both changes in within-pair social context and changes in the fertility of neighbouring females up to 400 m away. Within the social pair, males drastically reduced their song production when mated, but the magnitude of this reduction depended on both the time of day and on the fertility status of the social mate. By contrast, when fertile females were present on nearby territories, males increased their song output, especially during daytime singing. At this time, it is unclear whether males actively gathered information on neighbouring female fertility or whether the patterns that we observed were driven by changes in social interactions that varied with neighbourhood fertility. Regardless of the mechanism employed, however, subtle changes in the social environment generated substantial variation in signalling effort.