As the global landscape shifts into an era of Great Power Competition, characterized by unconventional threats and complex geopolitical dynamics, the need for a reimagined Office of Strategic Services (OSS) framework has never been more pressing. The revival of an OSS 2.0 would empower the Department of Defense (DoD) with enhanced Human Intelligence (HUMINT) capabilities that are critical for navigating the intricacies of Irregular Warfare (IW). Leveraging an updated OSS concept, the DoD could build deeper, longer-lasting relationships with foreign partners and local populations, laying the foundation for invaluable intelligence collection and clandestine or covert operations.