Modern music consumption largely relies on streaming services due to significant advancements in digital technologies. The offered freemium-premium business models have effectively facilitated a user to explore and experience the platform. This chapter documents a case study that can help the re-design of an existing music streaming service, Gaana, which is considered as one of the commercially largest in India. Accordant with the previous studies, the degree of effectiveness of a user experience can be an influential contributor in a user’s decision to subscribe and retain in the current music streaming service in use. The study emphasizes evaluating user interaction and interface effectiveness through user experience investigation, employing the double-diamond design methodology for in-depth insights. The research included user interviews and as an understanding of the outcome, Gaana emerged as a popular music streaming service with a vast collection of songs and albums by various Indian and global artists, attracting a wide user base. As the study progressed, it was found that there is also a significant amount of discontent attached to the user experience of the application. As per the recent changes in the application with respect to subscription charges, it is found that the application has now become a paid-only service for the users. Both factors have negatively impacted the user’s inclination to transition from freemium to premium model of usage and user’s retention to utilize the application. However, complete podcasts are still available for non-subscribers. As a result, many enthusiastic Gaana users have switched to competitors offering better free services. The research provides insights into how user experience impacts future usage of music streaming services.