Ethical decision-making is a critical aspect of human judgment, and the growing use of LLMs in decision-support systems necessitates a rigorous evaluation of their moral reasoning capabilities. However, existing assessments primarily rely on single-step evaluations, failing to capture how models adapt to evolving ethical challenges. Addressing this gap, we introduce the Multi-step Moral Dilemmas (MMDs), the first dataset specifically constructed to evaluate the evolving moral judgments of LLMs across 3,302 five-stage dilemmas. This framework enables a fine-grained, dynamic analysis of how LLMs adjust their moral reasoning across escalating dilemmas. Our evaluation of nine widely used LLMs reveals that their value preferences shift significantly as dilemmas progress, indicating that models recalibrate moral judgments based on scenario complexity. Furthermore, pairwise value comparisons demonstrate that while LLMs often prioritize the value of care, this value can sometimes be superseded by fairness in certain contexts, highlighting the dynamic and context-dependent nature of LLM ethical reasoning. Our findings call for a shift toward dynamic, context-aware evaluation paradigms, paving the way for more human-aligned and value-sensitive development of LLMs.

Despite advances in improving large language model (LLM) to refuse to answer malicious instructions, widely used LLMs remain vulnerable to jailbreak attacks where attackers generate instructions with distributions differing from safety alignment corpora. New attacks expose LLMs’ inability to recognize unseen malicious instructions, highlighting a critical distributional mismatch between training data and real-world attacks that forces developers into reactive patching cycles. To tackle this challenge, we propose **IMAGINE**, a synthesis framework that leverages embedding space distribution analysis to generate jailbreak-like instructions. This approach effectively fills the distributional gap between authentic jailbreak patterns and safety alignment corpora. IMAGINE follows an iterative optimization process that dynamically evolves text generation distributions across iterations, thereby augmenting the coverage of safety alignment data distributions through synthesized data examples. Based on the safety-aligned corpus enhanced through IMAGINE, our framework demonstrates significant decreases in attack success rate on Qwen2.5, Llama3.1, and Llama3.2 without compromising their utility.