As AI assistants become widely used, privacy-aware platforms like Anthropic's Clio have been introduced to generate insights from real-world AI use. Clio's privacy protections rely on layering multiple heuristic techniques together, including PII redaction, clustering, filtering, and LLM-based privacy auditing. In this paper, we put these claims to the test by presenting CLIOPATRA, the first privacy attack against "privacy-preserving" LLM insight systems. The attack involves a realistic adversary that carefully designs and inserts malicious chats into the system to break multiple layers of privacy protections and induce the leakage of sensitive information from a target user's chat. We evaluated CLIOPATRA on synthetically generated medical target chats, demonstrating that an adversary who knows only the basic demographics of a target user and a single symptom can successfully extract the user's medical history in 39% of cases by just inspecting Clio's output. Furthermore, CLIOPATRA can reach close to 100% when Clio is configured with other state-of-the-art models and the adversary's knowledge of the target user is increased. We also show that existing ad hoc mitigations, such as LLM-based privacy auditing, are unreliable and fail to detect major leaks. Our findings indicate that even when layered, current heuristic protections are insufficient to adequately protect user data in LLM-based analysis systems.

Current approaches to LLM safety fundamentally rely on a brittle cat-and-mouse game of identifying and blocking known threats via guardrails. We argue for a fresh approach: robust safety comes not from enumerating what is harmful, but from deeply understanding what is safe. We introduce Trust The Typical (T3), a framework that operationalizes this principle by treating safety as an out-of-distribution (OOD) detection problem. T3 learns the distribution of acceptable prompts in a semantic space and flags any significant deviation as a potential threat. Unlike prior methods, it requires no training on harmful examples, yet achieves state-of-the-art performance across 18 benchmarks spanning toxicity, hate speech, jailbreaking, multilingual harms, and over-refusal, reducing false positive rates by up to 40x relative to specialized safety models. A single model trained only on safe English text transfers effectively to diverse domains and over 14 languages without retraining. Finally, we demonstrate production readiness by integrating a GPU-optimized version into vLLM, enabling continuous guardrailing during token generation with less than 6% overhead even under dense evaluation intervals on large-scale workloads.

Machine learning models are known to leak sensitive information, as they inevitably memorize (parts of) their training data. More alarmingly, large language models (LLMs) are now trained on nearly all available data, which amplifies the magnitude of information leakage and raises serious privacy risks. Hence, it is more crucial than ever to quantify privacy risk before the release of LLMs. The standard method to quantify privacy is via membership inference attacks, where the state-of-the-art approach is the Robust Membership Inference Attack (RMIA). In this paper, we present InfoRMIA, a principled information-theoretic formulation of membership inference. Our method consistently outperforms RMIA across benchmarks while also offering improved computational efficiency. In the second part of the paper, we identify the limitations of treating sequence-level membership inference as the gold standard for measuring leakage. We propose a new perspective for studying membership and memorization in LLMs: token-level signals and analyses. We show that a simple token-based InfoRMIA can pinpoint which tokens are memorized within generated outputs, thereby localizing leakage from the sequence level down to individual tokens, while achieving stronger sequence-level inference power on LLMs. This new scope rethinks privacy in LLMs and can lead to more targeted mitigation, such as exact unlearning.

Large language models (LLMs) are increasingly used in modern search and answer systems to synthesize multiple, sometimes conflicting, texts into a single response, yet current pipelines offer weak incentives for sources to be accurate and are vulnerable to adversarial content. We introduce Truthful Text Summarization (TTS), an incentive-aligned framework that improves factual robustness without ground-truth labels. TTS (i) decomposes a draft synthesis into atomic claims, (ii) elicits each source's stance on every claim, (iii) scores sources with an adapted multi-task peer-prediction mechanism that rewards informative agreement, and (iv) filters unreliable sources before re-summarizing. We establish formal guarantees that align a source's incentives with informative honesty, making truthful reporting the utility-maximizing strategy. Experiments show that TTS improves factual accuracy and robustness while preserving fluency, aligning exposure with informative corroboration and disincentivizing manipulation.