This research monograph introduces the Singularization Framework, a theoretical model for diagnosing structural fragility in complex adaptive systems (CAS). Contrary to traditional approaches that interpret systemic collapse primarily as a consequence of entropy growth, chaos, or external shocks, this work proposes an alternative hypothesis: complex systems frequently fail due to absolutized order, a condition in which structural optimization suppresses adaptive variance and feedback permeability. The framework integrates three central components. First, the Mallinckrodt Cycle models the lifecycle of complex systems as a dynamic oscillation between expansion, optimization, structural compression, and collapse. Second, the Compression–Resonance–Tension Index (CRTI) provides a diagnostic metric designed to quantify systemic fragility through the interaction of three variables: structural compression (C), systemic resonance (R), and accumulated tension (T). Third, the concept of Strategic Reserve is introduced as a design principle for resilient architectures, emphasizing structural redundancy, cognitive diversity, and modular decentralization as buffers against systemic over-compression. The theoretical model is positioned at the intersection of cybernetics, network science, and complexity research. It extends classical concepts such as Ashby’s Law of Requisite Variety by addressing the inverse phenomenon: the suppression of variety through structural over-optimization. By combining graph-theoretical metrics, semantic entropy proxies, and nonlinear time-series indicators, the framework outlines possible pathways for empirical operationalization across financial systems, organizations, technological ecosystems, and geopolitical structures. Rather than offering a deterministic prediction of collapse, the Singularization Framework proposes a diagnostic lens for early detection of systemic fragility. The approach suggests that resilient systems maintain a balance between efficiency and adaptive redundancy. When this balance is lost, increasing compression and tension combined with declining resonance can push a system beyond a critical threshold, resulting in sudden structural breakdown. This work is presented as a theoretical synthesis intended to stimulate interdisciplinary discussion and further empirical investigation within the fields of complex systems science, cybernetics, and resilience research. Keywords (für Zenodo) complex systems system fragility resilience cybernetics network science structural compression CRTI Mallinckrodt Cycle system collapse complex adaptive systems