# Between a Rock and a Hard Place: The Tension Between Ethical Reasoning and Safety Alignment in LLMs

arXiv: https://arxiv.org/abs/2509.05367 · HTML: https://mlsanity.com/paper/2509.05367/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Reasoning for agents, planning and code, one of 17 directions in LLM reasoning.
- Builds on 29 of its 71 references that are in the map.
- First posted on arXiv 4 Sep 2025.

## Placed in

- LLM reasoning / [Reasoning for agents, planning and code](https://mlsanity.com/lr/reasoning-for-agents-planning-and-code/)
- LLM alignment / RLHF / preference optimisation / [Safety alignment and jailbreak attacks](https://mlsanity.com/alignment/safety-alignment-and-jailbreak-attacks/)
- LLM safety and security / [Safety alignment, refusal and guardrails](https://mlsanity.com/safety/safety-alignment-refusal-and-guardrails/)

## Builds on (most cited first, 29 of 29)

- [GPT-4 Technical Report](https://mlsanity.com/paper/2303.08774/) (2023)
- [The Llama 3 Herd of Models](https://mlsanity.com/paper/2407.21783/) (2024)
- [Training Verifiers to Solve Math Word Problems](https://mlsanity.com/paper/2110.14168/) (2021)
- [Training a Helpful and Harmless Assistant with Reinforcement Learning from Human Feedback](https://mlsanity.com/paper/2204.05862/) (2022)
- [Mistral 7B](https://mlsanity.com/paper/2310.06825/) (2023)
- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (2023)
- [Constitutional AI: Harmlessness from AI Feedback](https://mlsanity.com/paper/2212.08073/) (2022)
- [Jailbreaking Black Box Large Language Models in Twenty Queries](https://mlsanity.com/paper/2310.08419/) (2023)
- [Representation Engineering: A Top-Down Approach to AI Transparency](https://mlsanity.com/paper/2310.01405/) (2023)
- [Llama Guard: LLM-based Input-Output Safeguard for Human-AI Conversations](https://mlsanity.com/paper/2312.06674/) (2023)
- [Fine-tuning Aligned Language Models Compromises Safety, Even When Users Do Not Intend To!](https://mlsanity.com/paper/2310.03693/) (2023)
- [DeepSeek-V3 Technical Report](https://mlsanity.com/paper/2412.19437/) (2024)
- [Red Teaming Language Models to Reduce Harms: Methods, Scaling Behaviors, and Lessons Learned](https://mlsanity.com/paper/2209.07858/) (2022)
- [Baseline Defenses for Adversarial Attacks Against Aligned Language Models](https://mlsanity.com/paper/2309.00614/) (2023)
- [Eliciting Latent Predictions from Transformers with the Tuned Lens](https://mlsanity.com/paper/2303.08112/) (2023)
- [SmoothLLM: Defending Large Language Models Against Jailbreaking Attacks](https://mlsanity.com/paper/2310.03684/) (2023)
- [LLMs Get Lost In Multi-Turn Conversation](https://mlsanity.com/paper/2505.06120/) (2025)
- [Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack](https://mlsanity.com/paper/2404.01833/) (2024)
- [DeepInception: Hypnotize Large Language Model to Be Jailbreaker](https://mlsanity.com/paper/2311.03191/) (2023)
- [AutoDAN-Turbo: A Lifelong Agent for Strategy Self-Exploration to Jailbreak LLMs](https://mlsanity.com/paper/2410.05295/) (2024)
- [Latent Adversarial Training Improves Robustness to Persistent Harmful Behaviors in LLMs](https://mlsanity.com/paper/2407.15549/) (2024)
- [A Survey of Large Language Models for Healthcare: from Data, Technology, and Applications to Accountability and Ethics](https://mlsanity.com/paper/2310.05694/) (2023)
- [LLM Defenses Are Not Robust to Multi-Turn Human Jailbreaks Yet](https://mlsanity.com/paper/2408.15221/) (2024)
- [LLMs know their vulnerabilities: Uncover Safety Gaps through Natural Distribution Shifts](https://mlsanity.com/paper/2410.10700/) (2024)
- [Ethical Reasoning over Moral Alignment: A Case and Framework for In-Context Ethical Policies in LLMs](https://mlsanity.com/paper/2310.07251/) (2023)
- [FalseReject: A Resource for Improving Contextual Safety and Mitigating Over-Refusals in LLMs via Structured Reasoning](https://mlsanity.com/paper/2505.08054/) (2025)
- [Automatic Pseudo-Harmful Prompt Generation for Evaluating False Refusals in Large Language Models](https://mlsanity.com/paper/2409.00598/) (2024)
- [Faster-GCG: Efficient Discrete Optimization Jailbreak Attacks against Aligned Large Language Models](https://mlsanity.com/paper/2410.15362/) (2024)
- [AmpleGCG-Plus: A Strong Generative Model of Adversarial Suffixes to Jailbreak LLMs with Higher Success Rates in Fewer Attempts](https://mlsanity.com/paper/2410.22143/) (2024)

## Abstract (arXiv)

Large Language Model safety alignment predominantly operates on a binary assumption that requests are either safe or unsafe. This classification proves insufficient when models encounter ethical dilemmas, where the capacity to reason through moral trade-offs creates a distinct attack surface. We formalize this vulnerability through TRIAL, a multi-turn red-teaming methodology that embeds harmful requests within ethical framings. TRIAL achieves high attack success rates across most tested models by systematically exploiting the model's ethical reasoning capabilities to frame harmful actions as morally necessary compromises. Building on these insights, we introduce ERR (Ethical Reasoning Robustness), a defense framework that distinguishes between instrumental responses that enable harmful outcomes and explanatory responses that analyze ethical frameworks without endorsing harmful acts. ERR employs a Layer-Stratified Harm-Gated LoRA architecture, achieving robust defense against reasoning-based attacks while preserving model utility.