New technologies create novel issues and inform our understanding of existing laws. The statutes that form the basis of the U.S. IP regime are decades old and, as such, could not have contemplated how technology (and technology-assisted infringement) would evolve. As a result, traditional methods of IP enforcement often lag behind the rapidly changing online environment. Though Congress has taken steps to modernize these sometimes antiquated laws—for example, the America Invents Act made significant changes to the U.S. patent system in 2016 and the Music Modernization Act updated the music licensing and royalty framework to account for digital streaming platforms like Spotify in 2018—these updates almost always function as an ex post solution to a problem that was already present. The core questions of what is “protectable,” what is “infringement” and what is “willful” in view of the fundamental shifts in technological advancement remain squarely in the gray.