Imagine being immersed in your favorite song, only to be disrupted by an unsettling advertisement. Yet, instead of leaving, millions, especially Millennials and Gen Z, stay loyal to the platform, with many even moving to premium. What truly explains this paradox? This study aims to provide a comprehensive explanation regarding how service convenience, personalization, and interactive experience provide value to customers and how they would affect their premium subscription purchase intention with generation moderating the relationship. A hundred and twenty-five Spotify users were given an online questionnaire about service convenience, personalization, interactive experience, perceived value, and purchase intention. The result showed that service convenience, personalization, and interactive experience positively affect purchase intention while mediated by perceived value. Furthermore, service convenience and interactive experience positively affected customer perceived value while moderated by generation, and the effect was significantly greater for Generation Z compared to Generation Y. However, the effect of personalization on perceived value was not moderated by generation. Regarding purchase intention, the result showed that service convenience and interactive experience positively affected purchase intention while mediated by perceived value and moderated by generation, while personalization positively affects purchase intention mediated by perceived value but not moderated by generation.