When Can Conformal Risk Control Certify LLM Outputs? Bounds, Impossibility, and Adaptation for Structured Generation

Large language models (LLMs) deployed for structured generation (NER, JSON extraction, QA, and classification) lack formal reliability guarantees, and standard heuristic abstention policies miss user-specified risk targets by 7.5--12.5%. We characterize when conformal risk control (CRC) can certify structured LLM outputs and when it provably cannot. First, we prove an impossibility result: when the base risk (μ> α), any distribution-free method must abstain on at least ((μ-α)/(1-α)) examples, yielding a closed-form feasibility test: one can check whether CRC will work before running it. Second, we analyze a certification hierarchy across Hoeffding, empirical Bernstein, and a betting-based e-CRC bound, with strict gains in low-variance/large-sample regimes: the Hoeffding-to-Bernstein step delivers the largest gain (+37% certified configurations), while e-CRC adds value when calibration data is scarce (10% certification at 20% data versus 0% for Hoeffding). Third, we validate adaptive conformal inference (ACI) under cross-dataset shift, reducing risk-target violations from 71% to 21%, with residual failures concentrated exactly where the impossibility bound predicts. Across six open-weight models (3B--72B parameters), eight datasets, four tasks, and six nonconformity scores, hard NER/QA/CLS configurations are uncertifiable at (α= 0.10); relaxing to (α= 0.30--0.40) unlocks practical certification (47% NER, 40% QA, 60% CLS). The framework gives a three-step deployment recipe: check feasibility, select the bound and score, then mitigate shift.