Piracy is taking on an entirely new character in the age of media in the cloud. Global technology and business models are evolving rapidly, while regulators and lawmakers are catching up in attempts to work out a new set of rules of engagement. In this article, I explore the divergent developments between a retrograde global copyright governance regime and cloud-based media distribution that focuses on connectivity and access. I also examine attempts at business model innovation that seek to effectively embrace and control the continually evolving user–content–platform interaction in the cloud. This article will contribute to our understanding of this rapidly changing ecosystem and the dynamics between technology, law and market.