Large Language Models (LLMs) are commonly evaluated for robustness against paraphrased or semantically equivalent jailbreak prompts, yet little attention has been paid to linguistic variation as an attack surface. In this work, we systematically study how linguistic styles such as fear or curiosity can reframe harmful intent and elicit unsafe responses from aligned models. We construct style-augmented jailbreak benchmark by transforming prompts from 3 standard datasets into 11 distinct linguistic styles using handcrafted templates and LLM-based rewrites, while preserving semantic intent. Evaluating 16 open- and close-source instruction-tuned models, we find that stylistic reframing increases jailbreak success rates by up to +57 percentage points. Styles such as fearful, curious and compassionate are most effective and contextualized rewrites outperform templated variants. To mitigate this, we introduce a style neutralization preprocessing step using a secondary LLM to strip manipulative stylistic cues from user inputs, significantly reducing jailbreak success rates. Our findings reveal a systemic and scaling-resistant vulnerability overlooked in current safety pipelines.

Despite recent rapid progress in AI safety, current large language models remain vulnerable to adversarial attacks in multi-turn interaction settings, where attackers strategically adapt their prompts across conversation turns and pose a more critical yet realistic challenge. Existing approaches that discover safety vulnerabilities either rely on manual red-teaming with human experts or employ automated methods using pre-defined templates and human-curated attack data, with most focusing on single-turn attacks. However, these methods did not explore the vast space of possible multi-turn attacks, failing to consider novel attack trajectories that emerge from complex dialogue dynamics and strategic conversation planning. This gap is particularly critical given recent findings that LLMs exhibit significantly higher vulnerability to multi-turn attacks compared to single-turn attacks. We propose DialTree-RPO, an on-policy reinforcement learning framework integrated with tree search that autonomously discovers diverse multi-turn attack strategies by treating the dialogue as a sequential decision-making problem, enabling systematic exploration without manually curated data. Through extensive experiments, our approach not only achieves more than 25.9% higher ASR across 10 target models compared to previous state-of-the-art approaches, but also effectively uncovers new attack strategies by learning optimal dialogue policies that maximize attack success across multiple turns.