This study examines why two military innovation processes developed within the same organizational and political context can result in divergent outcomes. Through a comparative case study of two modernization programs in the U.S. Army, Future Combat Systems and Stryker Brigade Combat Team, the analysis focuses on how the internal dynamics of innovation processes shape their eventual results. Existing research on military innovation has largely emphasized successful cases and structural explanations for why innovation occurs. In contrast, this study adopts a process-oriented analytical framework to conduct a structured comparison of the programs’ design, implementation, and organizational conditions. The findings indicate that differences in how critical thinking were applied within each program contributed significantly to their divergent outcomes. The study contributes to the literature on military innovation and challenges the assumption that innovation is inherently synonymous with success.