Large language models (LLMs) rely on static pretraining corpora, resulting in outdated knowledge over time. Existing approaches for evaluating knowledge edits either suffer from rapid contamination or rely on counterfactual edits that conflict with rigid existing knowledge. In this work, we propose a simulation-driven approach for evaluating and training LLMs on knowledge insertions. We introduce PARALLELEVENTS, a benchmark that simulates coherent trajectories of fictional yet realistic future events, enabling controlled evaluation without data contamination or conflicts with existing knowledge. We further propose SYNAPSE, a training framework that leverages model-generated data to integrate new knowledge into model parameters via instruction tuning. This synthetic pipeline enables scalable knowledge integration without costly human-curated data. SYNAPSE improves QA accuracy by 14.23 points over prior methods, indicating that simulation-based synthetic training yields robust, coherent knowledge insertion.
Large language models (LLMs) can serve as helpful assistants, yet they can equally function as harm amplifiers that enable malicious users to achieve harmful outcomes beyond their capabilities through extended interactions. This risk manifests along two axes, i.e., democratizing domain expertise that allows novices to produce specialized harmful content, and scaling harmful operations at volumes that manual effort cannot match. Existing works, however, often overlook how LLMs compound harm across multi-turn conversations. We introduce HarmAmp, a new benchmark for multi-turn harm amplification scenarios spanning twelve risk categories. Each scenario is grounded in real-world threats and satisfies rigorous criteria, i.e., substantive amplification, operational specificity, and multi-turn necessity. We further propose TrajSafe, a proactive monitor that anticipates harmful trajectories and intervenes through actions such as probing users' genuine intents and steering the models towards safer completion. Our extensive experiments demonstrate that TrajSafe significantly reduces the harmfulness incurred in multi-turn interactions while preserving a low over-refusal rate and the target model's general capabilities. Our work offers a promising paradigm to alleviate the nuanced safety risks in LLM interactions.