The recent development of animal-borne sensors coupled with location data can provide insights into how individuals modify their behaviour with respect to specific habitat features. Animals can express a diverse array of behaviours as they navigate heterogenous landscapes, yet few studies have specifically evaluated the interaction of behaviours with habitat characteristics. We used a novel broadcast acoustic transmitter to investigate the interaction between vocal behaviours of an endemic Hawaiian thrush, the ʻōmaʻo, Myadestes obscurus, and habitat features across a naturally fragmented forest landscape. Through the development of behavioural landscape models that link specific vocalizations with space use, we found that the use of different vocalization types (calls, songs, whisper songs) were highly variable across the landscape but were associated with distinct habitat features. The likelihood of calls increased in an open lava matrix between forest patches, while whisper songs were more strongly associated with the dense interior areas of forest fragments. In contrast, the rate of ʻōmaʻo vocalizations overall decreased in the open lava matrix, suggesting that ʻōmaʻo may shift behaviours from territory defence to foraging as they transition through different habitats. Our study revealed context-specific changes in behaviour across ʻōmaʻo home ranges, including courtship, aggression and social interactions between individuals. Combining the use of a novel acoustic tool with automated radiotelemetry allowed us to overcome challenges associated with detection and analysis of variation in behaviour and resource selection across a highly heterogeneous landscape that would have been otherwise difficult to impossible.