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This paper examines the October 7, 2023 Hamas attack on Israel as a failure of interpretation rather than of intelligence collection within the U.S. intelligence community. Drawing on process tracing, comparative historical analysis, and triangulated open-source material, it reconstructs the pre-attack warning environment, the structure of U.S.–Israeli intelligence liaison, and the organizational seams that rendered Gaza analytically peripheral. The paper argues that delegated warning to Israeli services, policy-driven analytic triage, and heavy reliance on signals intelligence (SIGINT) produced an intelligence system saturated with data yet unable to recognize its strategic significance. Situating October 7 within a broader pattern of strategic surprise, the paper identifies recurring dynamics of doctrinal rigidity, analytic inertia, and the misreading of asymmetric adversaries. Conceptually, it calls for rethinking strategic warning in asymmetric conflicts away from prediction and toward interpretive adaptability, adversary-centric analysis, and institutional receptivity to weak and unconventional signals. The paper concludes that without addressing liaison dependency, alignment-driven politicization, and the epistemological limits of technological dominance, intelligence communities will remain prone to “knowing without seeing” precisely where surprise is most consequential.