Helpful to a Fault: Measuring Illicit Assistance in Multi-Turn, Multilingual LLM Agents
Organizations: Independent Researcher · EPFL, Switzerland · KIIT Bhubaneswar, India · ELLIS Institute Tübingen, MPI for Intelligent Systems, Tübingen AI Center, Germany
Abstract
LLM-based agents execute real-world workflows via tools and memory. These affordances enable ill-intended adversaries to also use these agents to carry out complex misuse scenarios. Existing agent misuse benchmarks largely test single-prompt instructions, leaving a gap in measuring how agents end up helping with harmful or illegal tasks over multiple turns. We introduce STING (Sequential Testing of Illicit N-step Goal execution), an automated red-teaming framework that constructs a step-by-step illicit plan grounded in a benign persona and iteratively probes a target agent with adaptive follow-ups, using judge agents to track phase completion. We further introduce an analysis framework that models multi-turn red-teaming as a time-to-first-jailbreak random variable, enabling analysis tools like discovery curves, hazard-ratio attribution by attack language, and a new metric: Restricted Mean Jailbreak Discovery. Across AgentHarm scenarios, STING yields substantially higher illicit-task completion than single-turn prompting and chat-oriented multi-turn baselines adapted to tool-using agents. In multilingual evaluations across six non-English settings, we find that attack success and illicit-task completion do not consistently increase in lower-resource languages, diverging from common chatbot findings. Overall, STING provides a practical way to evaluate and stress-test agent misuse in realistic deployment settings, where interactions are inherently multi-turn and often multilingual.
Figures & tables
| Target Agent | Single- | STING (Multi-turn) | X-Teaming | |
|---|---|---|---|---|
| Model | turn | |||
| Qwen3-Next | 35.1 6.1 | 72.7 4.1 | 67.8 4.5 | 27.0 4.9 |
| GPT-5.1 | 24.3 5.3 | 34.1 5.5 | 29.7 5.3 | 5.0 2.2 |
| Gemini 3 Flash | 45.9 6.2 | 50.9 5.5 | 47.6 5.8 | 13.8 4.0 |
| Claude Sonnet 4.5 | 16.0 4.8 | 32.3 5.6 | 28.0 5.4 | 2.2 1.4 |
| DeepSeek-V3.2 | 31.2 5.5 | 61.8 4.7 | 57.2 4.9 | 15.1 4.1 |
| Model | Chinese | French | Ukrainian | Hindi | Urdu | Telugu |
|---|---|---|---|---|---|---|
| Qwen3-Next | [0.76, 1.20] | [0.95, 1.44] | [0.73, 1.16] | [0.62, 0.98] | [0.80, 1.35] | [0.44, 0.74] |
| GPT-5.1 | [0.73, 1.38] | [0.84, 1.53] | [0.83, 1.65] | [0.98, 1.95] | [0.79, 1.47] | [0.87, 1.69] |
| Gemini 3 Flash | [0.84, 1.29] | [1.04, 1.64] | [1.11, 1.79] | [0.94, 1.58] | [1.18, 2.08] | [0.72, 1.37] |
| Model | English | Chinese | French | Ukrainian | Hindi | Urdu | Telugu |
|---|---|---|---|---|---|---|---|
| Qwen3 Next | 79.2 4.1 | 75.0 4.4 | 75.1 4.4 | 74.0 4.8 | 79.1 3.9 | 76.8 4.0 | 76.2 4.4 |
| GPT-5.1 | 77.8 4.1 | 72.6 4.5 | 69.6 4.6 | 72.2 4.5 | 77.5 4.2 | 77.3 4.4 | 77.3 4.6 |
| Gemini 3 Flash | 76.0 4.8 | 72.9 5.0 | 73.0 5.0 | 73.3 5.0 | 74.7 5.1 | 74.9 4.8 | 73.9 4.9 |
| No Tool Hint | With Tool Hint | |||
|---|---|---|---|---|
| Target Agent | AHS | ASR (%) | AHS (%) | ASR (%) |
| Qwen3-Next | 72.6 6.5 | 82.9 7.4 | 73.1 5.4 | 87.4 6.2 |
| GPT-5.1 | 31.4 7.3 | 49.8 10.2 | 36.7 8.1 | 38.6 9.7 |
| Gemini 3 Flash | 49.9 7.3 | 62.6 10.2 | 51.8 7.6 | 56.7 10.2 |
| Claude Sonnet 4.5 | 30.4 7.1 | 25.9 9.1 | 34.5 8.2 | 31.7 9.1 |
| DeepSeek-V3.2 | 59.5 6.7 | 67.0 9.7 | 63.9 6.8 | 69.5 10.2 |
| Setting | Defense | English | Chinese | French | Ukrainian | Hindi | Urdu | Telugu |
| Single-Turn Benign | PromptGuard | -1.5 | 0 | 0 | 0 | 0 | 0 | 0 |
| Safety Prompt | -5.7 | -5.7 | -5.9 | -5.8 | -5.7 | -5.8 | -5.8 | |
| Omni-Moderation | 0.0 | 0.0 | 0.0 | -1.1 | 0.0 | -0.9 | 0.0 | |
| STING (Multi-Turn) Harmful | PromptGuard | -3.8 | -2.4 | -0.3 | -0.4 | -0.8 | -0.1 | 0 |
| Safety Prompt | -38.9 | -38.2 | -34.8 | -33.3 | -40.5 | -38.9 | -36.7 | |
| Omni-Moderation | -12.5 | -12.0 | -17.2 | -10.8 | -7.7 | -7.1 | -2.4 |
Appendix figures & tables9 assets
Supplementary material from the paper’s appendix.
Appendix
| Strategist | English | Ukrainian | Telugu |
|---|---|---|---|
| Gemini 3 Pro | 63.2 (67.8) | 55.7 (70.5) | 53.5 (72.3) |
| Qwen3.5-27B | 53.3 (55.7) | 42.9 (60.9) | 42.1 (59.8) |
| Setting | English | Ukrainian | Telugu |
|---|---|---|---|
| Original | 67.9 | 70.1 | 71.1 |
| WE | 70.7 | 72.4 | 70.1 |
| WA+WE | 67.8 | 70.5 | 72.3 |
| WS+WA+WE | 55.7 | 60.9 | 59.8 |
| Language | No-Thinking | Thinking | ||
|---|---|---|---|---|
| AHS (%) | ASR (%) | AHS (%) | ASR (%) | |
| English | 72.8 4.1 | 85.2 5.1 | 65.2 5.0 | 87.5 4.8 |
| Ukrainian | 75.1 3.8 | 84.7 5.1 | 64.2 4.7 | 81.2 6.0 |
| Telugu | 74.4 3.4 | 80.2 6.0 | 65.1 4.8 | 74.4 6.5 |
| Language | No-Thinking | Medium | High | |||
|---|---|---|---|---|---|---|
| AHS (%) | ASR (%) | AHS (%) | ASR (%) | AHS (%) | ASR (%) | |
| English | 34.1 5.3 | 44.4 7.1 | 30.3 5.1 | 37.4 6.8 | 31.5 5.0 | 44.2 7.4 |
| Ukrainian | 37.1 5.0 | 50.5 7.4 | 32.0 5.1 | 42.6 7.4 | 35.0 5.5 | 44.7 7.4 |
| Telugu | 40.5 5.3 | 49.2 7.4 | 32.9 5.3 | 35.8 7.1 | 35.4 5.3 | 37.6 7.4 |
| Model | English | French | Hindi | Telugu |
|---|---|---|---|---|
| Qwen3-Next | 67.9 | 68.7 (67.1) | 71.2 (73.4) | 69.0 (71.1) |
| Gemini 3 Flash | 47.0 | 47.1 (46.3) | 47.9 (48.7) | 44.5 (46.6) |
| Language | Token Ratio | Similarity |
|---|---|---|
| Chinese | 0.98 | 0.727 |
| French | 1.32 | 0.751 |
| Ukrainian | 1.85 | 0.734 |
| Hindi | 2.94 | 0.696 |
| Urdu | 2.32 | 0.656 |
| Telugu | 4.97 | 0.509 |
| Language | ASR (%) | AHS |
|---|---|---|
| French | 89.20 | 72.01 |
| Urdu | 88.64 | 76.42 |
| Chinese | 85.23 | 75.08 |
| English | 85.23 | 72.57 |
| Ukrainian | 84.66 | 75.02 |
| Hindi | 82.95 | 77.64 |
| Setting | Model | English (PG/SP) | Ukrainian (PG/SP) | Telugu (PG/SP) |
|---|---|---|---|---|
| Single-Turn Benign | GPT-5.1 | -1.5 / -2.7 | 0.0 / -1.9 | 0.0 / -5.4 |
| Gemini 3 Flash | -1.5 / -2.0 | 0.0 / -5.9 | 0.0 / -0.6 | |
| STING (Multi-Turn) Harmful | GPT-5.1 | -0.3 / -13.8 | -1.1 / -16.8 | -1.5 / -25.7 |
| Gemini 3 Flash | -1.2 / -41.1 | -0.8 / -44.1 | 0.0 / -47.4 |
| Setting | Defense | English | Chinese | French | Ukrainian | Hindi | Urdu | Telugu |
|---|---|---|---|---|---|---|---|---|
| Single-Turn | PromptGuard | [-3.7, 0.0] | 0 | 0 | 0 | 0 | 0 | 0 |
| Benign | Safety Prompt | [-9.4, -2.4] | [-9.4, -2.1] | [-9.4, -2.6] | [-9.3, -2.3] | [-9.3, -2.3] | [-9.9, -1.9] | [-9.6, -2.2] |
| Multi-Turn | PromptGuard | [-6.9, -1.4] | [-4.7, -0.6] | [-1.0, 0.0] | [-1.4, 0.0] | [-1.9, 0.0] | [-0.3, 0.0] | 0 |
| Harmful | Safety Prompt | [-46.3, -31.9] | [-45.0, -32.0] | [-42.1, -27.5] | [-39.8, -27.0] | [-46.87, -33.82] | [-45.6, -32.4] | [-43.14, -30.26] |
LLM Red Teaming
Large language model red teaming probes how models and agents can be induced to violate safety, security, or operational constraints.
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