The ability to make and execute timely and effective decisions has been the foundation of military success for millennia. In the next decade, however, Combined Force Air Component Commanders (CFACC) planning, decision, and execution (PDE) cycles will be confronted by unprecedented challenges emerging in the constantly evolving digital ecosystem. The era of unrivaled access to the electromagnetic spectrum and dominance in multiple domains is rapidly coming to a close for the US airpower. As more and more state and non-state actors gain access to advanced technology, the CFACC’s PDE cycles will transition from an observe, orient, decide, act (OODA) loop to an OODA point. This phenomenon will also have a significant influence on the command, control, communications, computers, intelligence, surveillance, and reconnaissance (C4ISR) measures necessary to shape and execute preplanned and emergent decisions in contested operational environments. One way of mitigating these nascent vulnerabilities is to develop a deliberate framework of operational design focused on airpower to provide a proactive form of vision for future CFACCs.