This study introduces the concept of cumulative historicity as a fundamental mechanism governing the structuring of transformational trajectories within complex systems. As a continuation of previous investigations devoted to organizational persistence and transformational continuity, it develops a theoretical framework for examining how past transformations influence future trajectories, organizational regimes, and reorganization mechanisms. A series of exploratory numerical simulations is used to analyze various emergent behaviors, including transformational locking, attractor mutation, systemic fragmentation, multi-scale compensation, and the coexistence of competing regimes. The results highlight the emergence of persistent historical structures capable of constraining, orienting, or modifying the future evolution of trajectories. They also suggest the existence of distinct organizational regimes associated with different degrees of continuity, stability, and adaptability. This study constitutes a consolidation stage of the ICMM-FW program and opens the way toward the study of the topology of transformational spaces, the geometry of organizational regimes, and transformational invariants. Scientific Contact:Frédéric CordierEmail: cordierfr@wanadoo.fr or frederic.cordier@alcahest-quantique.frORCID: 0009-0001-8661-3275Project page: https://www.alcahest-quantique.fr