The singer-songwriter is aligned with notions of authenticity in popular music discourse. In recent years, one part of this discourse has focused on singer-songwriters’ connections with “local” people, places and issues (Zuberi 2007). This essay considers the notion of local authenticity with respect to Don McGlashan, a New Zealand singer-songwriter, using Moore’s (2005) persona-environment model as a method for examining, holistically, the songs in their broader critical context. Moore’s approach considers how a musical environment shapes a listener’s understanding of the song’s persona. Two songs, ‘Andy’ and ‘Dominion Road,’ are discussed. I argue that aspects of the songs’ environments—stylistic setting, harmonic language, and rhythmic ambiguities—frame and reinforce the persona’s words and situations. Thus, rather than undercutting the lyrics, the musical content serves to strengthen and authenticate further McGlashan’s expressions of New Zealand.