This paper addresses the longstanding tension between cyclic conceptions oftime and the thermodynamic arrow imposed by the Second Law of Thermodynamics.Classical cyclic models, whether cosmological or philosophical, require theuniverse to return to prior states, yet quantitative analysis of entropy production inradiative, gravitational, chemical, and quantum processes demonstrates that suchexact recurrence is overwhelmingly improbable. Using explicit estimates of entropygrowth across astrophysical and terrestrial systems, we show that cumulative irreversibilityrenders traditional cyclic evolution physically untenable.To resolve this conflict, we propose a reformulation in which cyclicity is not attributedto the dynamical evolution of the universe but to the structure of observerdependentexperience within a fixed spacetime manifold. Adopting an eternalist orblock-universe ontology consistent with relativity, we model observers as worldlinesand introduce a formal reassignment operator acting on sequences of consciousstates. This operator permits cyclic experiential ordering without requiring anyviolation of thermodynamic laws or reversal of entropy gradients.We develop the framework using tools from statistical mechanics, general relativity,and quantum theory, including entropy functionals, density matrix evolution,and spacetime geometry. We further analyze continuity and identity under discontinuousexperiential mappings, drawing analogies with wormhole geometries anddecoherence-induced effective discontinuities. The resulting model preserves causalstructure and physical continuity while allowing a form of recurrence grounded inexperiential reassignment rather than physical repetition.This approach reframes the problem of cyclic time as one of ontology and observerstructure rather than cosmological dynamics. While it avoids the thermodynamicinconsistencies of classical cyclic models, it raises new questions concerningthe nature of consciousness, identity, and temporal ordering within the block universe.These issues are discussed along with implications for the philosophy of timeand the foundations of physics.