Francesco Giarrusso

We present evidence that adversarial poetry functions as a universal single-turn jailbreak technique for Large Language Models (LLMs). Across 25 frontier proprietary and open-weight models, curated poetic prompts yielded high attack-success rates (ASR), with some providers exceeding 90%. Mapping prompts to MLCommons and EU CoP risk taxonomies shows that poetic attacks transfer across CBRN, manipulation, cyber-offence, and loss-of-control domains. Converting 1,200 MLCommons harmful prompts into verse via a standardized meta-prompt produced ASRs up to 18 times higher than their prose baselines. Outputs are evaluated using an ensemble of 3 open-weight LLM judges, whose binary safety assessments were validated on a stratified human-labeled subset. Poetic framing achieved an average jailbreak success rate of 62% for hand-crafted poems and approximately 43% for meta-prompt conversions (compared to non-poetic baselines), substantially outperforming non-poetic baselines and revealing a systematic vulnerability across model families and safety training approaches. These findings demonstrate that stylistic variation alone can circumvent contemporary safety mechanisms, suggesting fundamental limitations in current alignment methods and evaluation protocols.

Jailbreaking techniques pose a significant threat to the safety of Large Language Models (LLMs). Existing defenses typically focus on single-turn attacks, lack coverage across languages, and rely on limited taxonomies that either fail to capture the full diversity of attack strategies or emphasize risk categories rather than jailbreaking techniques. To advance the understanding of the effectiveness of jailbreaking techniques, we conducted a structured red-teaming challenge. The outcomes of our experiments are fourfold. First, we developed a comprehensive hierarchical taxonomy of jailbreak strategies that systematically consolidates techniques previously studied in isolation and harmonizes existing, partially overlapping classifications with explicit cross-references to prior categorizations. The taxonomy organizes jailbreak strategies into seven mechanism-oriented families: impersonation, persuasion, privilege escalation, cognitive overload, obfuscation, goal conflict, and data poisoning. Second, we analyzed the data collected from the challenge to examine the prevalence and success rates of different attack types, providing insights into how specific jailbreak strategies exploit model vulnerabilities and induce misalignment. Third, we benchmarked GPT-5 as a judge for jailbreak detection, evaluating the benefits of taxonomy-guided prompting for improving automatic detection. Finally, we compiled a new Italian dataset of 1364 multi-turn adversarial dialogues, annotated with our taxonomy, enabling the study of interactions where adversarial intent emerges gradually and succeeds in bypassing traditional safeguards.

Safety mechanisms in LLMs remain vulnerable to attacks that reframe harmful requests through culturally coded structures. We introduce Adversarial Tales, a jailbreak technique that embeds harmful content within cyberpunk narratives and prompts models to perform functional analysis inspired by Vladimir Propp's morphology of folktales. By casting the task as structural decomposition, the attack induces models to reconstruct harmful procedures as legitimate narrative interpretation. Across 26 frontier models from nine providers, we observe an average attack success rate of 71.3%, with no model family proving reliably robust. Together with our prior work on Adversarial Poetry, these findings suggest that structurally-grounded jailbreaks constitute a broad vulnerability class rather than isolated techniques. The space of culturally coded frames that can mediate harmful intent is vast, likely inexhaustible by pattern-matching defenses alone. Understanding why these attacks succeed is therefore essential: we outline a mechanistic interpretability research agenda to investigate how narrative cues reshape model representations and whether models can learn to recognize harmful intent independently of surface form.