# A Systematic Investigation of RL-Jailbreaking in LLMs

arXiv: https://arxiv.org/abs/2605.07032 · HTML: https://mlsanity.com/paper/2605.07032/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Jailbreaking, one of 12 directions in LLM safety and security.
- Builds on 57 of its 75 references that are in the map.
- First posted on arXiv 7 May 2026.

## Placed in

- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)

## Builds on (most cited first, 30 of 57)

- [Proximal Policy Optimization Algorithms](https://mlsanity.com/paper/1707.06347/) (2017)
- [The Llama 3 Herd of Models](https://mlsanity.com/paper/2407.21783/) (2024)
- [Sentence-BERT: Sentence Embeddings using Siamese BERT-Networks](https://mlsanity.com/paper/1908.10084/) (2019)
- [Qwen3 Technical Report](https://mlsanity.com/paper/2505.09388/) (2025)
- [Judging LLM-as-a-Judge with MT-Bench and Chatbot Arena](https://mlsanity.com/paper/2306.05685/) (2023)
- [Evaluating Large Language Models Trained on Code](https://mlsanity.com/paper/2107.03374/) (2021)
- [Efficient Memory Management for Large Language Model Serving with PagedAttention](https://mlsanity.com/paper/2309.06180/) (2023)
- [BERTScore: Evaluating Text Generation with BERT](https://mlsanity.com/paper/1904.09675/) (2019)
- [Qwen2-VL: Enhancing Vision-Language Model's Perception of the World at Any Resolution](https://mlsanity.com/paper/2409.12191/) (2024)
- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (2023)
- [Deep Reinforcement Learning with Double Q-learning](https://mlsanity.com/paper/1509.06461/) (2015)
- [SWE-agent: Agent-Computer Interfaces Enable Automated Software Engineering](https://mlsanity.com/paper/2405.15793/) (2024)
- [Jailbroken: How Does LLM Safety Training Fail?](https://mlsanity.com/paper/2307.02483/) (2023)
- [HarmBench: A Standardized Evaluation Framework for Automated Red Teaming and Robust Refusal](https://mlsanity.com/paper/2402.04249/) (2024)
- [RealToxicityPrompts: Evaluating Neural Toxic Degeneration in Language Models](https://mlsanity.com/paper/2009.11462/) (2020)
- [Red Teaming Language Models with Language Models](https://mlsanity.com/paper/2202.03286/) (2022)
- [Universal Adversarial Triggers for Attacking and Analyzing NLP](https://mlsanity.com/paper/1908.07125/) (2019)
- [The Linear Representation Hypothesis and the Geometry of Large Language Models](https://mlsanity.com/paper/2311.03658/) (2023)
- [Tree of Attacks: Jailbreaking Black-Box LLMs Automatically](https://mlsanity.com/paper/2312.02119/) (2023)
- [WildChat: 1M ChatGPT Interaction Logs in the Wild](https://mlsanity.com/paper/2405.01470/) (2024)
- [How Johnny Can Persuade LLMs to Jailbreak Them: Rethinking Persuasion to Challenge AI Safety by Humanizing LLMs](https://mlsanity.com/paper/2401.06373/) (2024)
- [BERT-ATTACK: Adversarial Attack Against BERT Using BERT](https://mlsanity.com/paper/2004.09984/) (2020)
- ["Do Anything Now": Characterizing and Evaluating In-The-Wild Jailbreak Prompts on Large Language Models](https://mlsanity.com/paper/2308.03825/) (2023)
- [GPT-4 Is Too Smart To Be Safe: Stealthy Chat with LLMs via Cipher](https://mlsanity.com/paper/2308.06463/) (2023)
- [A StrongREJECT for Empty Jailbreaks](https://mlsanity.com/paper/2402.10260/) (2024)
- [DeepInception: Hypnotize Large Language Model to Be Jailbreaker](https://mlsanity.com/paper/2311.03191/) (2023)
- [RLPrompt: Optimizing Discrete Text Prompts with Reinforcement Learning](https://mlsanity.com/paper/2205.12548/) (2022)
- [A Holistic Approach to Undesired Content Detection in the Real World](https://mlsanity.com/paper/2208.03274/) (2022)
- [ShieldGemma: Generative AI Content Moderation Based on Gemma](https://mlsanity.com/paper/2407.21772/) (2024)
- [Adversarial GLUE: A Multi-Task Benchmark for Robustness Evaluation of Language Models](https://mlsanity.com/paper/2111.02840/) (2021)

## Abstract (arXiv)

The evolution of generative models from next-token predictors to autonomous engines of complex systems necessitates rigorous safety hardening. Adversarial jailbreaking, the strategic manipulation of models to elicit harmful output, remains a primary threat to safe deployment. While Reinforcement Learning (RL) frames jailbreaking as a multi-step attack through sequential optimization, a mechanistic understanding of why the framework succeeds remains incomplete. To fill this gap, we present the first systematic decomposition of RL jailbreaking. We deconstruct the framework into problem formalization (reward function, action space, episode length), and algorithmic measures (RL algorithm, training data, reward-shaping) to identify the structural determinants of adversarial success. Our results reveal that the RL-jailbreaker successfully compromised all targeted models and safeguards. Through this first-of-its-kind analysis, we demonstrate that environment formalization, specifically dense rewards and extended episode lengths, is the primary driver of jailbreaking success. This work provides a tool for improving RL-jailbreaker efficiency and, ultimately, harden generative models resistant to RL-based attacks.