Although the genetic and ecological effects of population declines in endangered species have been well studied, little is known of the social consequences. Changes in signaling behavior may result in disrupted communication and affect both reproductive and conflict-resolution activities. The North Island Kōkako (Callaeas wilsoni) is an endangered, duetting (i.e., alternating, coordinated singing by mated pairs) songbird endemic to New Zealand temperate rain forests. Scattered populations (approximately 1500 individuals in 13 surviving and 11 translocated populations) in isolated conservation areas of different sizes have been rescued from extirpation and are currently recovering. We examined key song attributes of the Kōkako to assess whether population size or growth rate are related to song complexity, the reduction of which may compromise effective communication. We analyzed song repertoire size and phrase-type sharing (i.e., Jaccard index of similarity), vocal performance (singing rates, song switching rates, and diversity of phrase types), and song syntactical characteristics (i.e., unpredictability in sequences of phrase types) in surviving and translocated populations (populations of approximately 19–250 territorial individuals). Population size was positively correlated with a population's song repertoire, song diversity, and switching of song phrase types and negatively correlated with shared phrase types and variation in syntactical structure of songs. Population growth rate correlated positively with pair repertoire size, population repertoire size, and singing rates during song bouts. As for solo-singing species in fragmented landscapes, songs in the fragmented populations of Kōkako appear to be undergoing microevolution as occurs in island colonization events. Our results suggest that vocal changes in small populations could affect population establishment and growth, particularly in multiple-source translocations. We believe measurement of vocal behavior could be used as a supplement to periodic population censuses to allow more frequent monitoring of population size.