Background Civilization increasingly rely on symbolic stabilization — including law, money, theology, and artificial intelligence — to coordinate growing social and cognitive complexity. Historically, however, highly stabilized symbolic systems repeatedly exhibit tendencies toward partial detachment from the heterogeneous realities they originally emerged to organize. Objectives This paper introduces a minimal conceptual distinction between adequacy and stabilization in order to examine recurrent structural similarities across theological, economic, and contemporary AI systems. Methods Using comparative historical and conceptual analysis, the paper examines three domains: the emergence of Purgatory and indulgence structures in late medieval Christianity; the increasing autonomy of monetary and financial abstraction within economic organization; and the operation of contemporary large language models based on statistical symbolic reproduction. Results Across all three domains, increasing operational success is shown to strengthen the autonomous expansion of stabilizing structures themselves. Systems originally developed to coordinate heterogeneous realities progressively begin to prioritize internally reproducible regularities over situational adequacy. Literary narrative and irony further emerge as important supplementary modes of representation where analytical language encounters growing difficulty in describing highly autonomous symbolic environments. Conclusions The primary historical risk identified in this study lies not in symbolic stabilization itself, which remains indispensable for large-scale coordination, but in the gradual reversal whereby systems originally created to preserve adequacy increasingly reproduce themselves through partially autonomous symbolic operations. Contemporary large language models may represent a technologically intensified form of this broader historical tendency