Numerous studies have shown that streaming is now the most preferred way of consuming multimedia content and this is evidenced by the proliferation in the number of streaming service providers as well as the exponential growth in their subscriber base. Riding on the advancements in low cost electronics, high speed communication and extremely cheap data, Over-The-Top (OTT) music streaming is now the norm in the music industry and is worth millions of dollars. This is especially true in India where major players offer the so called freemium models which have active monthly user bases running in to the millions. These services namely, Gaana, Airtel Wynk and JioSaavn attract a significantly bigger audience than their 100% subscription based peers like Amazon Prime Music, Apple Music etc. Given their ubiquity and market dominance, it is pertinent to do a systematic analysis of these platforms so as to ascertain their potential as hotbeds of piracy. This work investigates the resilience of the content protection systems of the four biggest music streaming services (by subscriber base) from India, namely Airtel Wynk, Ganna, JioSaavn and Hungama. By considering the Digital Rights Management (DRM) system employed by Spotify as a benchmark, we analyse the security of these platforms by attempting to steal the streamed content efficiently. Finally, we present a holistic overview of the flaws in their security mechanisms and discuss possible mitigation strategies. To the best of our knowledge, this work constitutes the first attempt to analyze security of OTT music services from India. Our results further confirm the time tested belief that security through obscurity is not a long term solution and leaves such platforms open to piracy and a subsequent loss of revenue for all the stakeholders.