Large Language Models Can Follow Instructions, But Not Many at Once: Phase Transitions in Compositional Constraint Satisfaction

Large language models are increasingly deployed in settings that require simultaneous adherence to multiple explicit constraints - reasoning structure, safety boundaries, output schemas. Individual constraints are handled proficiently, but the compositional regime, where many must hold jointly, remains poorly characterized: how rapidly does performance degrade, what governs the degradation, and can the collapse be mitigated? We introduce Constraint Saturation Evaluation (CSE), a procedurally generated benchmark that systematically varies the number of simultaneous constraints (k), with every constraint scored by a deterministic, rule-based verifier and zero LLM-judge involvement: 15 models, 36 constraint types, 369,753 checks at k=1-12. Three findings emerge. First, per-constraint pass rate decays gradually and predictably, while the chance of satisfying all k constraints collapses - a model passing individual constraints at ~41% at k=8 succeeds on all eight just 5.7% of the time. Second, constraints do not degrade equally: structural constraints lose 2x more baseline capability per added constraint than lexical ones, ordered by a comprehension-maintenance gap that separates constraints requiring sustained tracking from binary decisions immune to composition. Third, failures are nearly independent, which is what makes the accumulation multiplicative; the residual coupling that does exist tracks shared output features rather than pairwise interference - a wrong sentence count fails every constraint that reads it. Reliable instruction following breaks down beyond 5-6 simultaneous constraints: probe-level success falls below 50% at 7 constraints for the strongest model, and at 3 or fewer for 12 of 15.