This paper extends on the initial findings of “Application of Artificial Intelligence in the National Airspace System: A Primer”(Stroup & Niewoehner: Herndon, VA; ICNS-2019), and looks at why the current technologies, enterprise architecture, and future program plans may not be enough to address persistent operational challenges. This paper further explores why emergent operational concepts, business models, and demand profiles may necessitate AI-enhanced Communications, Navigation and Communications (CNS) infrastructure to disrupt current operational impediments. European airspace, as well as the NAS, has similar challenges. Key challenges explored in this study include: quantifiable improvements to NAS capacity, efficiency, and resiliency; traffic flow management of diverse users; UTM-ATM airspace integration; equitable access to airspace; and airborne-ground interoperability of AI applications. Finally, we examine why trustworthiness and resiliency will be key mileposts on the regulatory pathway to AI certification.