This article examines the production of musical nostalgia in High School Musical: The Musical: The Series (2019–23), one of the first series created for Disney’s streaming platform. On one level, the series serves as a nostalgic extension of the High School Musical franchise in its setting and narrative construction, and a nostalgic continuation of the teen-musical genre in its idealised depiction of high-school life mediated through song. At the same time, this nostalgia is coupled with an emphasis on the show’s newness: the series transposes the original film to a new format—a self-referential, multi-episodic mockumentary—and occupies a different temporal world, in which nostalgia is technologically mediated and constructed as part of the diegesis. Focusing on music, as a primary sensory input for the evocation of nostalgia, this study explores how The Series capitalises upon this nostalgia/modernity dichotomy to structure its narrative and engender brand affinity. Drawing together textual analyses of audiovisual sequences and practitioner testimony from the show’s creatives, it demonstrates how The Series uses music to develop Disney’s brand, harnessing the technological and creative promise of the Company’s proprietary streaming service, whilst simultaneously employing nostalgic strategies to reaffirm the status quo in aspects of its narrative.