Music Streaming Services (MSS) have recently emerged as the main format for showcasing and monetizing sound recordings by record labels and artists in the international recorded music sector. In the Caribbean, however, stakeholders have been slow to adopt and integrate these digital music platforms into their overall recorded music strategies. Within this context, this paper explores the key economic opportunities and challenges associated with the late adoption of the platform-based streaming music model. Using self-administered structured interviews with nine regional experts from the three major music markets, as well as an analysis of audio-visual and digital materials and review of documents, the information is derived using a qualitative research approach, supported by a grounded theory strategy of inquiry. The findings illustrate that on one hand there is cautious optimism with respect to the potential for the re-construction of revenue streams, due to stronger royalty inflows associated with new uses of music in the digital arena. The extent to which this is realized contends with the quantum of royalty payouts actually received by rights-holders and their overall willingness to licence their rights to MSS. Additionally, MSS provides the platform for rights-owners to reach glocal audiences. However, this is reliant on the content and user-friendly features embedded in the platforms and the readiness of regional artists to be discovered and monetized via third party playlists.