Safety alignment in LLMs aims to align models with human values, but which values take precedence when they conflict? We investigate this question in the context of tool-calling LLM agents deployed in regulated industries, where agents processing confidential documents may encounter content that triggers safety-trained values (e.g., public welfare) that conflict with deployment-context instructions (e.g., internal logging). To empirically verify this phenomenon, we build a benchmark of 128 scenarios across 16 domains. We find that safety-aligned open-source models override their deployment instructions up to 43.4% of the time, engaging in whistleblowing, data exfiltration, and evidence tampering when processing documents that suggest organizational wrongdoing. We also find that abliteration reduces rates of external whistleblowing. These results reveal a fundamental tension in pluralistic alignment, where the same safety training that protects users can cause agents to act against deployment instructions in ways that create unpredictable liability risks. We release our benchmark as a framework to support evaluation of agent behavior under competing legitimate interests.
Tool-using LLM agents increasingly rely on external tools to make consequential decisions, yet most existing agent-security benchmarks and defenses implicitly assume that tool feedback is trustworthy once a tool has been selected. We study a different failure mode, cognitive poisoning, in which a malicious tool behaves plausibly during exploration, accumulates trust through benign-looking feedback, and becomes harmful only when hidden state conditions align with the final executable action. To study this setting, we construct TRUST-Bench, a task-conditioned benchmark of 1,970 hidden-trigger tool-compromise episodes with matched safe controls, introduce an asymmetric penalty metric, GuardedJoint, to better reflect real deployment risk, and present VISTA-Guard, a backbone-agnostic framework for final-action risk scoring. The core idea is to abstract multi-step tool interaction into structured environment variables that encode trust-formation dynamics and then score the risk of the final executable action from this trajectory-conditioned representation. Experiments show that prompt-centric heuristics, scalarized features, and zero-shot judges fail in this regime, whereas trajectory-aware final-action scoring yields strong in-domain discrimination and remains effective under balanced out-of-distribution transfer. Under GuardedJoint, VISTA-Guard reaches 84.2 in-domain and 56.9 on balanced out-of-distribution evaluation, while methods that optimize only one side of the safety--utility tradeoff collapse to zero. These findings support a broader view of agent security in black-box tool ecosystems: the decisive defense target is not local prompt text or tool descriptors alone, but the way trust is formed across the interaction trajectory and committed through the final action.
Frontier LLMs are increasingly deployed as agents that pick the next action after a long log of prior tool calls produced by the same or a different model. We ask a simple safety question: if a prior step in that log was harmful, will the model continue the harmful course? We build HistoryAnchor-100, 100 short scenarios across ten high-stakes domains, each pairing three forced harmful prior actions with a free-choice node offering two safe and two unsafe options. Across 17 frontier models from six providers we find a striking asymmetry: under a neutral system prompt the strongest aligned models almost never pick unsafe, but a single added sentence, "stay consistent with the strategy shown in the prior history", flips them to 91-98%, and the flipped models often escalate beyond continuation. Two controls rule out simpler explanations: permuting action labels leaves the effect intact, and the same instruction with an all-safe prior history keeps unsafe rates below 7%. Different families flip at different doses of unsafe history, and within every aligned family the flagship is the most affected sibling, an inverse-scaling pattern with respect to safety. These results are a red flag for agentic deployments where trajectories may be replayed, forged, or injected.
Tool-using language-model agents introduce security failures that go beyond unsafe text: they can disclose protected objects, write persistent memory, send messages, modify databases, or trigger harmful code and tool effects. Existing evaluations often collapse these stages into a single attack success rate, making it difficult to tell whether a model merely agreed with an attacker or actually produced observable harm. We introduce SafeClawBench, a staged benchmark for tool-using agent security with 600 controlled adversarial tasks across six attack families: direct and indirect prompt injection, tool-return injection, memory poisoning, memory extraction, and ambiguity-driven unsafe inference. SafeClawBench reports three separate endpoints: semantic attack acceptance, audit-visible harm evidence, and sandbox-observed tool/state harm. Evaluating five agent endpoints under four prompt-level policies, we find that these endpoints capture different failure modes. Without additional prompt protection, semantic failure rates vary widely across models, from 9.0% to 44.2%. Audited harm evidence is narrower than semantic failure, and under a separate executable protocol some matched task identities produce sandbox harm despite passing the Semantic Core call: in a 12,000-row matched analysis, 291 of 347 observed sandbox harms occur in rows that pass the semantic check. Prompt policies change endpoint outcomes, but their effects depend on both model and protocol. SafeClawBench provides a reproducible framework for comparing agent models and prompt-policy conditions without conflating textual compliance, evidence-supported harm, and executable state changes. The open-source dataset is available at https://huggingface.co/datasets/sairights/safeclawbench.