Surrogate Substitution Preserves PHI Detectability: A Multi-Detector Equivalence Study

LLM-based assistants transmit user queries verbatim to third-party API endpoints that lie outside the user's audit or control. When those queries contain personally identifiable information (PII), the data persists on remote infrastructure subject to breach, subpoena, or policy change. Placeholder redaction (the prevailing mitigation) suppresses PII at the cost of semantic coherence, producing structurally degraded queries and correspondingly degraded responses. We present SurrogateShield, a client-side proxy that substitutes detected PII with locally generated, type-consistent surrogate values prior to transmission and restores originals in the response. No real PII crosses the network boundary. Detection runs through a three-stage cascade (PatternScan, EntityTrace, and ContextGuard) covering 22 PII types and quasi-identifier combinations grounded in Sweeney's k-anonymity framework. Surrogate-to-original mappings are sealed in an AES-256-GCM encrypted per-conversation ShadowMap that never leaves the device. Evaluations on a 1,124-query corpus demonstrate that the cascade reliably detects PII, achieving an overall F1 score of 98.87%. Surrogate substitution substantially outperforms placeholder redaction in semantic utility, yielding a 13.26 pp improvement in BERTScore (roberta-large), from 81.59% to 94.85%. Within this corpus, the local pipeline restricted real PII transmission across all tested query types; in a 100-query adversarial trial, a prompted LLM adversary recovered no original values from surrogate-substituted messages.

De-identification of clinical text is a prerequisite for the secondary use of electronic health records. Existing public benchmarks such as the i2b2 2006 and 2014 corpora are over a decade old and lack the semantic and demographic diversity of modern clinical narratives. Large Language Models (LLMs) reach state-of-the-art zero-shot extraction, but their use at enterprise scale is limited by computational cost and by hospital data governance that restricts sending Protected Health Information (PHI) to cloud APIs. We introduce SHIELD (Synthetic Human-annotated Identifier-replaced Entries for Learning and De-identification), a diverse clinical note dataset of 1,381 notes with 10,229 gold-standard PHI spans across 9 categories, built with set-cover diversity sampling across demographic and document-type strata and human-in-the-loop adjudication. We evaluate four LLMs (two proprietary, two open-weight) to establish a performance ceiling on SHIELD, then show that a teacher-student distillation framework transfers these capabilities into locally deployable Small Language Models. Our best distilled model reaches micro-averaged span-level precision of 0.89 and recall of 0.88 while running on standard workstation hardware. It trails its cloud teacher on per-category recall (0.90 vs. 0.81 macro-averaged) but remains competitive given its lower cost and on-premise deployability. Cross-dataset evaluation shows that diversity-trained models generalize well on universal structured PHI categories, while institution-specific entities remain hard to transfer in both directions, which suggests pairing broad-coverage models with specialized models for high-volume, semi-structured note types. We publicly release the SHIELD dataset and the distilled DeBERTa v3 model to provide an accurate, cost-effective de-identification pipeline deployable entirely behind institutional firewalls.

Current text anonymization evaluation relies on span-based metrics that fail to capture what an adversary could actually infer, and assumes a single data subject, ignoring multi-subject scenarios. To address these limitations, we present SPIA (Subject-level PII Inference Assessment), the first benchmark that shifts the unit of evaluation from text spans to individuals, comprising 675 documents across legal and online domains with novel subject-level protection metrics. Extensive experiments show that even when over 90% of PII spans are masked, subject-level inference protection drops as low as 33%, leaving the majority of personal information recoverable through contextual inference. Furthermore, target-subject-focused anonymization leaves non-target subjects substantially more exposed than the target subject. We show that subject-level inference-based evaluation is essential for ensuring safe text anonymization in real-world settings.