A complex and interdependent environment in the Global War on Terrorism (GWOT) highlights the challenge of translating the theory of effects-based operations (EBO) into practice, particularly with respect to influencing the will of the people and achieving a desired endstate. The following paper seeks to illustrate the conditions and challenges surrounding the translation of current effects-based theory into operational practice in GWOT by using three conceptual constructs. First, the Microsoft Corporation, its connectivity to the Internet, and the persistent attacks by computer hackers on Microsoft products help frame the adversary and the complex environment and conditions surrounding GWOT. Second, the Al Jazeera satellite news network serves as an anecdotal backdrop for the challenges military planners face in managing EBO assessment and controlling the "effects" in EBO. Third, the versatility of both the MQ-1B Predator unmanned aerial vehicle and Special Operations Forces (SOF) illustrate the importance of developing and maintaining collective knowledge, technological relevance, and doctrinal adaptability in an ever-changing GWOT environment. Military planners who follow an effects-based strategy should recognize EBO's inherent limitations and plan for its characteristic uncertainty and uncontrollability.