arXiv:2610.36711v1 Announce Type: new Abstract: Reliable evaluation is a critical bottleneck in privacy red-teaming of large language models (LLMs): determining whether a jailbreak response actually reveals personal information can be difficult when disclosures are indirect, contextual, partial, or obfuscated. Existing evaluation approaches increasingly rely on guard models and LLM-as-Judges, yet these evaluators may interpret the same response differently. To better characterize this evaluation setting, we conduct a systematic study of privacy evaluators and find substantial disagreement, particularly in ambiguous cases that require additional evidence or targeted analysis to resolve. Motivated by these findings, we introduce \textsc{PrivacyEvalClaw}, a training-free deliberative agent for evaluating privacy leakage in LLM jailbreak responses. Rather than relying on isolated single-pass judgments, PrivacyEvalClaw treats evaluators and analysis modules as tools, adaptively gathers evidence, investigates uncertain disclosures, and reconciles conflicting signals before producing a final judgment. Our primary experiments use pairwise LLM-as-Judge evaluation of complete trajectories, showing that PrivacyEvalClaw achieves favorable win rates against competing baselines across outcome, process, and overall quality, while producing explicit reasoning traces that make the evaluation process more transparent and auditable.