Answer-Only Disclosure: Private-Context LLM Assistance over Web APIs with a Leakage Ledger

Leading large language model providers now conceal their models' step-by-step reasoning, or chain-of-thought, to protect intellectual property and limit information leakage. Rather than storing these traces server-side, providers return them to the client as blocks of encrypted text, which the client passes back with each subsequent request. Building on prior research, we identify an architectural vulnerability: these encrypted blocks are fully compatible and interchangeable across different sessions, users, and models within a provider's ecosystem. We exploit this compatibility to develop a scalable decryption jailbreak. By injecting an encrypted reasoning trace from a given model into a weaker, and less safeguarded model from the same provider, we force it to decode and output the trace verbatim in plaintext, without ever jailbreaking the more capable model directly. This vulnerability enables four distinct attack vectors. First, it circumvents anti-distillation mechanisms, allowing adversaries to extract a proprietary model's reasoning, as we demonstrate across Anthropic, OpenAI, and Google. Second, it allows for large-scale private data extraction. Developers frequently share session logs publicly, unaware of contents of the encrypted blocks. By decoding 315,320 reasoning blocks scraped from public repositories, we recovered 367 Personally Identifiable Information (PII) artifacts and 182 credentials. Third, it inadvertently reveals hazardous information hidden within the reasoning process, even in cases where the model's final, visible output safely rejects a malicious request. Fourth, attackers can leverage this flaw to execute invisible prompt injections, embedding malicious payloads entirely within encrypted blocks to poison public agentic rollouts. Following responsible disclosure, we propose concrete cryptographic and system-level mitigations to secure client-side reasoning.

Large language models increasingly operate as persistent assistants in user-facing, shared-session, and tool-augmented settings. When users disclose sensitive information during an active conversation, that information may remain behaviorally recoverable through later prompts even after the dialogue shifts to unrelated topics. We introduce PrivDrift, a benchmark for auditing whether user-disclosed secrets remain recoverable after conversational topic drift and persuasion-based probing. PrivDrift contains 1,000 controlled multi-turn dialogues with seeded secrets, content-dense drift turns, and standardized extraction probes. Across three LLMs with extended context windows, dialogue-level hybrid leakage remains substantial, ranging from 38.7% to 54.6%, and varies strongly by model, secret type, and persuasion intensity. Within the tested drift window, additional topic drift does not reliably reduce leakage, suggesting that privacy risk in active LLM contexts should be evaluated as a persistent behavioral failure mode rather than only as training-data memorization or immediate jailbreak behavior.

Large language model (LLM)-based personal agents are increasingly deployed to handle everyday tasks on users' behalf. These agents have access to private user information, while their tasks involve communicating with third parties; this raises a critical privacy concern that agents may inappropriately reveal sensitive user information to these recipients. Existing benchmarks primarily assess direct privacy leakage, where an agent explicitly states a pre-specified secret or attribute. However, they do not capture inferential leakage, where the model leaves indirect cues in the reply that implicitly leaks sensitive attributes. We introduce InferPriv, a benchmark that measures whether an honest-but-curious recipient can infer a user's sensitive attributes from an LLM's reply on routine task. Evaluating five frontier models, we find that inferential leakage substantially exceeds direct leakage across models and prompts. Under a privacy-aware system prompt, GPT-6.1-Sol, Sonnet-5.5, and Gemini-3.8-Flash achieve near-zero direct leakage, yet the inferential leakage rate remains between 16.2--25.2%. These findings suggest that evaluating explicit leakage alone can substantially understate the privacy risks.