Prompt Injection as Role Confusion

Indirect prompt injection poses a critical threat to LLM agents that interact with untrusted external data, yet automated attack methods--proven effective for jailbreaking--remain underexplored in realistic agentic settings. We present a comprehensive empirical evaluation of automated prompt injection attacks against LLM agents, adapting both white-box (GCG) and black-box (TAP) methods to the agentic setting within the AgentDojo framework. We evaluate across 80 task pairs spanning four domains and multiple models, and find that black-box optimization substantially outperforms gradient-based methods, a gap we attribute to GCG's optimization instability under reasonable compute budgets. We also find that TAP's effectiveness depends on the attacker model, as both general capability and safety tuning affect attack success--stronger models produce more effective injections, while safety-tuned attackers can refuse to generate adversarial prompts. Task-universal attacks transfer effectively to unseen tasks and out-of-distribution domains, but attacks optimized on smaller open-source models do not transfer to frontier models like GPT-5. These findings highlight automated prompt injection as a credible but model-dependent threat, with significant barriers remaining for model-agnostic exploitation.

Clarification-seeking behavior is widely regarded as a desirable property of LLM agents, enabling them to resolve ambiguity before acting on underspecified tasks. However, the security implications of this interaction pattern remain unexplored. We investigate whether the transition from standard execution to a clarification-seeking state increases an agent's susceptibility to prompt injection attacks. We introduce ASPI (Ambiguous-State Prompt Injection), a benchmark of 728 task-attack scenarios that isolates clarification as a distinct agent state and measures how this state transition affects vulnerability under controlled conditions. Each benchmark instance is evaluated under matched execution and clarification settings: in the execution setting, the agent acts on a fully specified instruction and encounters adversarial content only through tool-returned data; in the clarification setting, the agent must first request and incorporate additional user input before acting. We evaluate ten frontier LLMs and find that clarification-seeking consistently and substantially amplifies vulnerability. For instance, attack success rises from 1.8% to 34.0% for o3 and from 2.2% to 35.7% for Gemini-3-Flash. A decomposition analysis reveals that this gap reflects both a state-dependent shift in how models process incoming content and a channel-specific effect arising from the agent-solicited clarification interface. These findings demonstrate that standard execution-time security evaluation systematically underestimates the attack surface of interactive agents, and that robustness under fully specified tasks does not translate to robustness under ambiguity. For reproducibility, our data and source code are available at https://github.com/scaleapi/aspi.

Tool-augmented LLM agents are vulnerable to prompt injection: a third party who controls part of the agent's context can plant instructions that the agent then executes as if they came from the user. Current evaluations report a single attack success rate per model on one channel, the tool output and treat that number as the model's vulnerability. But tool descriptions, which the agent reads at every turn before any tool is called, are themselves an injection surface that the attacker can choose instead. We hold the injection payload byte-identical and deliver it through both surfaces across 13 LLMs from six families and four task suites. The same bytes invert in success rate across models: GPT-4.1 is 96 percent vulnerable on tool outputs but only 4 percent on tool descriptions, while GEMINI-3-FLASH shows the mirror pattern at 20 percent and 98 percent. A variance decomposition over 6,830 attempts attributes 0 percent of the variation in attack outcomes to the surface alone, while the model-surface interaction accounts for 16.7 percent. Vulnerability is a property of the pairing, not the channel. The Adaptive Attack Rate, defined as the per-cell maximum over surfaces, exceeds the strongest fixed-surface baseline by +9.1 percentage points on average. Standard prompt-level defenses inherit the same blindspot, reducing tool-output ASR to 10-18 percent while leaving the description channel above 54 percent. Both attack and defense evaluation must report per-surface vulnerability.