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Synapse
March 26, 20260 citationsOpen Access

The Enforcement Gap: Specification-Present Rationalization in Large Language Models

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SJSusanne de Jong

Key Points

  • This research aims to document and understand the failure modes of large language models when adhering to safety and reasoning specifications.
  • Conduct reproducible tests across four major commercial language models.
  • Develop a taxonomy of three distinct types of failure in reasoning and safety adherence.
  • Perform iterative testing to assess resilience of failures against various remediation strategies.
  • Identified a failure mode where language models recognize and violate safety constraints.
  • Established three distinct failure types related to reasoning paths.
  • Demonstrated that failure persists despite multiple remediation attempts at the prompt and specification levels.

Abstract

Large language models demonstrate a previously undocumented failure mode in which safety and reasoning specifications are read, correctly identified, and violated in the same processing step. The model does not lack the relevant knowledge. It does not misunderstand the constraint. It identifies the rule, names the prohibition, and proceeds to violate it through motivated reasoning — reasoning paths that formally satisfy a constraint while circumventing its intended effect — driven by helpfulness optimization. This paper documents the phenomenon through reproducible testing across four major commercial systems, presents a taxonomy of three distinct failure types, and establishes through iterative specification-level testing that the failure is robust to a range of prompt-layer and specification-level remediation attempts. The solution space is characterized as architectural, operating at a level below the specification layer.

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Cite This Study

Susanne de Jong (2026) studied this question.

synapsesocial.com/papers/69c4cda5fdc3bde44891a40ahttps://doi.org/10.5281/zenodo.19201964
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Also Consider

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  1. 1Empirical Evaluation of Reasoning LLMs in Machinery Functional Safety Risk Assessment and the Limits of Anthropomorphized Reasoning2025 · 8 citations
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  5. 5Measuring Reverse-Specification Quality Without Ground Truth: A Three-Layer Framework and a Pre-Registered Study of Scale-Induced Failure Modes in Autonomous Coding Agents2026