LLMStructBench: Benchmarking Large Language Model Structured Data Extraction

Large Language Models are increasingly being deployed to extract structured data from unstructured and semi-structured sources: parsing invoices, medical records, and converting PDF documents to database entries. Yet existing benchmarks for structured output generation either focus on schema compliance alone, or evaluate value correctness within a single source domain. We introduce SOB (The Structured Output Benchmark), a multi-source benchmark spanning three source modalities: native text, images, and audio conversations. All models receive a text-normalized representation of their context regardless of source modality; this deliberate design isolates structured-output capability from raw vision or speech-processing quality, ensuring a fair, source-agnostic comparison. Our benchmark comprises 5,000 text evaluation records derived from multi-hop QA drawn from a 25,091-record full corpus, 209 image records from OCR-processed PDFs across seven document types including multi-column layouts, dense tables, scanned historical documents, small-print text, and mathematical typesetting, and 115 audio records from the AMI corpus. Each record pairs a natural-language question with a JSON schema that the model must follow and a ground-truth answer verified against the source context. We evaluate 21 frontier and open-weight models across three source domains and seven metrics. Our results reveal a consistent pattern: models achieve near-perfect schema compliance, yet the best Value Accuracy, measured by exact leaf-value match, reaches only 83.0% on text, 67.2% on images, and 23.7% on audio, where longer context makes extraction substantially harder. We release the dataset, evaluation pipeline, and all related code.

Deploying large language models in production often requires constraining outputs to structured formats such as JSON or XML, and prior work treats the resulting accuracy loss as an inherent structure tax'. We re-examine this claim by evaluating a battery of models, datasets and schemas, measuring task accuracy, confidence calibration, and hidden-state geometry. The tax turns out to depend on schema design rather than on structure per se: reasoning-first field ordering matches or exceeds free-form accuracy, while answer-first ordering causes steep drops, particularly in smaller models. Format sensitivity scales inversely with a task's own structural constraints, and schemas that preserve reasoning order also improve calibration with CKA showing greater separability between correct and incorrect representations in middle transformer layers. Our findings indicate that properly designed structured formats can match or exceed free-form performance, reframing the critical question from whether to structure' to `how to structure' for optimal reasoning preservation.

Structured Outputs from current LLMs exhibit sporadic errors, hindering enterprise AI deployment. We present CONSTRUCT, a real-time uncertainty estimator that scores the trustworthiness of LLM Structured Outputs. Lower-scoring outputs are more likely to contain errors, enabling automatic prioritization of limited human review bandwidth. CONSTRUCT additionally scores the trustworthiness of each field within a Structured Output, helping reviewers quickly identify which parts of the output are incorrect. Our method is suitable for any LLM (including black-box LLM APIs without logprobs), does not require labeled training data or custom model deployment, and supports complex Structured Outputs with heterogeneous fields and nested JSON schemas. We also introduce one of the first public LLM Structured Output benchmarks with reliable ground-truth values. Over this four-dataset benchmark, CONSTRUCT detects errors in outputs from various LLMs (including Gemini 3 and GPT-5) with significantly higher precision/recall than existing techniques.