This study is an assessment of whether the US Air Force (USAF) should anticipate modernizing its core theater airlift fleet with aircraft designed for super-short takeoffs or landings under rough-field conditions (SSTOL-RF) or aircraft designs focused on vertical takeoffs or landings (VTOL) with secondary SSTOL-RF capabilities (V/SSTOL-RF). Several considerations speak to the timeliness of this issue. Most importantly, the ongoing evolution of USAF and Army (USA) war-fighting concepts increase their demand for mobility and sustainment support in quantities and places that the aircraft in the present airlift fleet cannot provide. Also, the present mainstay of the theater airlift fleet, the C-130, has been an inadequate platform for vital missions for decades. It is too small to link effectively and efficiently with large intertheater airlifters, such as the C-5, C-17, and civil reserve air fleet (CRAF) jumbo cargo aircraft at intermediate staging bases. Also, the C-130's runway requirements limit its ability to connect to battlefield airlift helicopters or deliver forces and sustainment at forward-most points of need and effect (PON/E) themselves. Intratheater airlift, consequently, is the weak link in the USAF's ability to provide a smooth flow of air and land combat forces and their sustainment in the early stages of conflicts and crises. Finally, although the USAF has not published a formal plan for theater airlift modernization, most officials interviewed for this study suggested sometime in the 2040s as the window for the next aircraft to appear. Given the experience of the C-17 program, which took 19 years to move from development contract to the first squadron reaching initial operational capability, a program aimed at putting a squadron of future theater airlifters on line by the middle 2040s should begin sometime in the early 2020s. As a contribution to conceptualizing the best path to a modern theater airlift fleet, then, this study will assess the SSTOL-RF and V/SSTOLRF design approaches in terms of their ability to fulfill critical USA and USAF requirements and their operational risk profiles.