This book examines some cognitive constructs such as worldview, implicit assumptions, and groupthink. Further, the monograph discusses biases such as anchoring, status quo bias, confirmation bias, sunk-cost bias, framing trap, halo and pitchfork effect, narrative fallacy, and the self-fulfilling prophecy bias. To examine the impact of these constructs on operational planning the monograph looks at the case book of the 1973 Arab-Israeli War. Documentation of this conflict provides insight into the inner workings of Israeli planning groups. Investigation of this case book allows the monograph to determine that Israeli leaders and planners struggled with cognitive biases. Further, planners struggled with flawed assumptions, faulty worldview, and groupthink. This resulted in impacts on Israeli operations and the relationships between operational planners and strategic leaders.