Beyond Detection: Evaluating Defensive LLMs Against AI-Generated Social Engineering in Live Turn-by-Turn Interaction

The empirical foundation of cyber deception relies on human-centered hypotheses, but the rapid emergence of autonomous, AI-enabled attackers challenges whether this foundation transfers to AI agents. To address this, we introduce an automated evaluation framework adapted from the Honeyquest instrument to assess LLM attacker judgment at scale. Our 21-LLM cohort spanned 10 providers, diverse architectures and specializations, open- and closed-weight models, and parameter scales from 8B to over 1T. We evaluated the performance of this LLM cohort (yielding 10,962 responses) against the 47-participant human baseline across an identical set of 174 reconnaissance queries. Our empirical evaluation reveals three key findings that establish LLMs as a distinct attacker class: (1) every model in our cohort falls for deceptive traps at a significantly higher rate than human attackers; (2) the defensive attention-diversion effect observed in humans is statistically absent in our LLM cohort; and (3) a critical recognition-action gap, where LLMs successfully articulate trap recognition in their reasoning but exploit the deceptive elements anyway 73.4% of the time. Across the 21 models, trap recognition in reasoning text did not predict fell-for-trap behavior (Spearman $r = +0.08$, $p = 0.73$). Ultimately, these findings demonstrate that human-centered deception hypotheses do not reliably transfer to AI attackers, highlighting the critical need for new research into AI-native active defense frameworks.

Defenses against indirect prompt injection (IPI) in tool-using LLM agents share two structural weaknesses. First, they all attempt to prevent attacks rather than detect the compromises that slip through. Second, they have only been evaluated in English, leaving users of low-resource languages such as Kurdish and Arabic without tested protection. This paper addresses both gaps with AgentShield, a deception-based detection framework that places three layers of traps inside the agent's tool interface: fake tools, fake credentials, and allowlisted parameters. The same trap triggers serve as high-precision labels for a self-supervised classifier. An LLM agent that follows an attacker's hidden instruction almost always touches one of these traps, which gives both a real-time compromise signal and a zero-FP label for training a downstream detector without manual annotation. Across 176 cross-lingual attack prompts and four LLMs from three providers, and because modern LLMs already refuse most IPI attempts on their own (attack success rate <= 10%), AgentShield's job is to catch the attacks that do slip through. On commercial models, it catches 90.7%-100% of such successful attacks, with zero false alarms on 485 normal-use tests. It survives a systematic adaptive-attack evaluation with zero evasion on commercial models, and the self-supervised classifier transfers across models and languages without retraining.

LLM-based agents process external content, exposing them to prompt injection and multi-turn manipulation. Most safety benchmarks evaluate defenders against fixed attack pools collected before evaluation, single-turn or multi-turn. We present a 21-scenario benchmark for \emph{adaptive multi-round attacks against memoryless LLM defenders}: an autonomous LLM attacker observes prior defender responses and pivots across rounds, while each defender response is evaluated as a fresh interaction. Holding the 21 scenarios, attackers, defenders, and structured-output scoring fixed, restricting scoring to the first attacker turn yields $0$-$1\%$ attack success rate (ASR); allowing 15 rounds of adaptive attack yields $5.4$-$14.0\%$. Pooling three frontier attacker LLMs uncovers $1.4$-$2.2\times$ as many unique successful attacks as the best single attacker, and the generated attacks have low cosine similarity ($0.02$-$0.14$) to attacks in existing benchmarks. Claude Opus 4.6 and GPT-5.4 are tied in aggregate ($5.4\%$ each; overlapping $95\%$ CIs), but their weaknesses differ sharply: on one scenario Opus reaches $60\%$ ASR ($95\%$ CI $36$--$80\%$) while GPT-5.4 and Gemini each stay at $7\%$ (CI $1$-$30\%$; the gap is preserved in a higher-$N$ replication). $13$ of $21$ scenarios distinguish at least one defender pair, yet rankings disagree across scenarios (Kendall's $W = 0.19$). We release the benchmark -- 21 evaluation scenarios, 10 public development scenarios, the orchestrator, baseline harnesses, and a multi-attacker CLI -- plus 945 transcripts from the 3$\times$3 frontier matrix, an attack-replay dataset, and 18{,}422 gpt-oss-20b battles from an open competition's final scoring rounds.