We present **CPTCoder**, a human-in-the-loop system that predicts standardized medical procedure codes from clinical text. Clinical procedure coding is an extreme multi-label classification problem over a long-tailed space of short numeric identifiers, where a single-digit difference denotes an entirely different procedure. CPTCoder adapts an instruction-tuned LLM with a code-aware vocabulary and constrained decoding that guarantees all outputs are valid codes. To support human review, we derive per-code posterior inclusion probabilities from n-best reweighting, producing interpretable confidence scores that rank predictions and flag uncertain cases. A post-decoding constraint repair step enforces mutual-exclusion rules between conflicting codes. To enable reproducible research in this underexplored setting, we release **MIMIC-CPT**, a PhysioNet-accessible benchmark of 37,885 expert-cleaned report–code pairs with a deliberately hardened test split: 88% of test examples contain label combinations unseen during training, and over a third include codes with five or fewer training occurrences. We additionally provide 413,085 weakly aligned pairs and evaluate on a separate live dataset from a hospital, which includes out-of-domain radiology reports with billing-expert-verified labels. CPTCoder achieves 0.61 and 0.51 micro-F1 on the hardened MIMIC split and Hospital-298 respectively, outperforming the strongest baseline by 12 and 5 absolute points while reducing digit-level near-miss errors.

Large language models (LLMs) have demonstrated promising performance on medical benchmarks; however, their ability to perform medical calculations, a crucial aspect of clinical decision-making, remains underexplored and poorly evaluated. Existing benchmarks often assess only the final answer with a wide numerical tolerance, overlooking systematic reasoning failures and potentially causing serious clinical misjudgments. In this work, we revisit medical calculation evaluation with a stronger focus on clinical trustworthiness. First, we clean and restructure the MedCalc-Bench dataset and propose a new step-by-step evaluation pipeline that independently assesses formula selection, entity extraction, and arithmetic computation. Under this granular framework, the accuracy of GPT-4o drops from 62.7% to 43.6%, revealing errors masked by prior evaluations. Second, we introduce an automatic error analysis framework that generates structured attribution for each failure mode. Human evaluation confirms its alignment with expert judgment, enabling scalable and explainable diagnostics. Finally, we propose a modular agentic pipeline, MedRaC, that combines retrieval-augmented generation and Python-based code execution. Without any fine-tuning, MedRaC improves the accuracy of different LLMs from 16.35% up to 53.19%. Our work highlights the limitations of current benchmark practices and proposes a more clinically faithful methodology. By enabling transparent and transferable reasoning evaluation, we move closer to making LLM-based systems trustworthy for real-world medical applications.