AgentRedBench: Dynamic Redteaming and Integration-Aware Defense for LLM Agents over SaaS Integrations

Indirect prompt injection in tool-use agents is a concrete production threat: LLM agents read from integrations (third-party services such as Gmail, Salesforce, or Jira accessed through tool calls) whose response content the user neither writes nor controls. Existing benchmarks under-measure the threat: most cover only a handful of integrations with the same attack payload replayed across runs, and open-source guards are trained on chat-style data rather than tool-response content. We introduce AGENTREDBENCH, a dynamic LLM-driven redteaming benchmark of 215 subtle underspecified authorization (attacks at the boundary of what the user's request authorises) scenarios across 24 enterprise integrations in nine functional families and five attack types. Across an eight-model panel (Anthropic, OpenAI, Google), no-guard ASR (attack success rate) ranges from 32% (Claude Sonnet 4.6) to 81% (Gemini 3 Flash). To keep the scenario set out of training corpora and preserve headline ASR meaning over time, we release the codebase, integration schemas, and AGENTREDGUARD model openly; the canonical scenarios are evaluated through a maintainer-mediated channel with immutable versioning. We release AGENTREDGUARD alongside the benchmark: a guard trained on an integration-diverse corpus of adversarial tool-response content. AGENTREDGUARD cuts panel ASR from 69.9% to 2.4% at 0.37% false-positive rate, outperforming every open-source baseline with non-trivial detection (Llama Guard, PromptGuard 2, ProtectAI) on both axes. Cross-integration and cross-attack type holdouts both confirm the gain transfers beyond the training subset.

Eliciting and Analyzing Emergent Misalignment in State-of-the-Art Large Language Models

Despite significant advances in alignment techniques, we demonstrate that state-of-the-art language models remain vulnerable to carefully crafted conversational scenarios that can induce various forms of misalignment without explicit jailbreaking. Through systematic manual red-teaming with Claude-4-Opus, we discovered 10 successful attack scenarios, revealing fundamental vulnerabilities in how current alignment methods handle narrative immersion, emotional pressure, and strategic framing. These scenarios successfully elicited a range of misaligned behaviors, including deception, value drift, self-preservation, and manipulative reasoning, each exploiting different psychological and contextual vulnerabilities. To validate generalizability, we distilled our successful manual attacks into MISALIGNMENTBENCH, an automated evaluation framework that enables reproducible testing across multiple models. Cross-model evaluation of our 10 scenarios against five frontier LLMs revealed an overall 76% vulnerability rate, with significant variations: GPT-4.1 showed the highest susceptibility (90%), while Claude-4-Sonnet demonstrated greater resistance (40%). Our findings demonstrate that sophisticated reasoning capabilities often become attack vectors rather than protective mechanisms, as models can be manipulated into complex justifications for misaligned behavior. This work provides (i) a detailed taxonomy of conversational manipulation patterns and (ii) a reusable evaluation framework. Together, these findings expose critical gaps in current alignment strategies and highlight the need for robustness against subtle, scenario-based manipulation in future AI systems.