Twenty-five years into the modern software industry, revenue growth is slowing, and relationships between software publishers and customers are frequently complicated by multiple mergers and acquisitions (M&A). Additionally, in today’s stringent regulatory environment, both publishers and enterprise customers must gain a clearer understanding of software ownership to ensure compliance with legal requirements. In parallel, a new industry for digitally distributed content is growing rapidly. Pervasive high-speed, high-bandwidth Internet connectivity allows all manner of content—not just software, but associated marketing, training and feedback on product usage, and platform demographics—to be exchanged with enterprise customers in a mutual, agreed-upon fashion. Beyond the long-term challenge of reforming software licensing practices, these opportunities pose the immediate question of how to license and provide entitlements for software published today.