The Conundrum of Trustworthy Research on Attacking Personally Identifiable Information Removal Techniques

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.

Personally Identifiable Information (PII) detection is a foundational component of data protection infrastructure where missed entities constitute direct privacy and security risks. Although modern PII systems report strong performance on standard benchmarks, we show that these evaluations mask substantial robustness failures under realistic distribution shifts encountered in deployment. Rather than comparing state-of-the-art accuracy, we study how different PII detection paradigms fail under noisy, unstructured, and informal inputs. We construct a stress test benchmark spanning seven categories of natural distribution shift and evaluate representative systems from three widely deployed architectural families: encoder-based NER (SpaCy), rule-based hybrid detection (Presidio), and generative LLM extraction (Qwen2.5-3B). All three exhibit significant degradation on out-of-distribution inputs, but with distinct and complementary failure modes. Encoder models primarily fail on unseen surface forms and boundary detection, rule-based systems fail on non-standard formats, and LLMs exhibit entity-type confusion and generation instability. These results show that aggregate benchmark scores obscure deployment-critical weaknesses and that no single architecture is uniformly reliable across PII categories. Motivated by these findings, we propose a hybrid detection pipeline with a QA-driven feedback loop for iterative risk mitigation, and release our benchmark to support OOD-aware evaluation of PII systems.

Browsing-enabled LLM assistants can fetch webpages and answer contact-seeking queries, creating a practical channel for scraping contact-style personally identifiable information (PII) from public pages. Many prior defenses are deployed at the model, service, or agent layer rather than at the webpage itself, leaving ordinary page owners with limited deployable options. We present PIIGuard, a webpage-level defense that repurposes indirect prompt injection as a protective mechanism: the page owner embeds optimized hidden HTML fragments that steer the model away from verbatim or reconstructible disclosure of contact PII. PIIGuard searches over fragment text and insertion position using rule-based leakage scoring, evolutionary mutation, and final judge-based recoverability assessment. In direct-HTML evaluation on three target models (GPT-5.4-nano, Claude-haiku-4.5, and DeepSeek-chat(latest v3.2)), PIIGuard achieves at least 97.0% defense success rate under both rule-based and judge-based leakage evaluation, often reaching 100.0%, while preserving benign same-page QA utility. We further evaluate two harder settings: public-URL browsing and attacker-side LLM sanitization of fetched webpage. These results show that page-side defensive fragments can remain effective in deployment for some model-position pairs, but robustness varies substantially across browsing interfaces and sanitizer prompts. Overall, PIIGuard demonstrates that page owners can use page-side fragments as a practical mitigation for web-grounded PII leakage.