We investigate long-context vulnerabilities in Large Language Models (LLMs) through Many-Shot Jailbreaking (MSJ). Our experiments utilize context length of up to 128K tokens. Through comprehensive analysis with various many-shot attack settings with different instruction styles, shot density, topic, and format, we reveal that context length is the primary factor determining attack effectiveness. Critically, we find that successful attacks do not require carefully crafted harmful content. Even repetitive shots or random dummy text can circumvent model safety measures, suggesting fundamental limitations in long-context processing capabilities of LLMs. The safety behavior of well-aligned models becomes increasingly inconsistent with longer contexts. These findings highlight significant safety gaps in context expansion capabilities of LLMs, emphasizing the need for new safety mechanisms.

We present the Conversational Data Retrieval (CDR) benchmark, the first comprehensive test set for evaluating systems that retrieve conversation data for product insights. With 1.6k queries across five analytical tasks and 9.1k conversations, our benchmark provides a reliable standard for measuring conversational data retrieval performance. Our evaluation of 16 popular embedding models shows that even the best models reach only around NDCG@10 of 0.51, revealing a substantial gap between document and conversational data retrieval capabilities. Our work identifies unique challenges in conversational data retrieval (implicit state recognition, turn dynamics, contextual references) while providing practical query templates and detailed error analysis across different task categories. The benchmark dataset and code are available at https://github.com/l-yohai/CDR-Benchmark.