Automated red teaming is an effective method for identifying misaligned behaviors in large language models (LLMs). Existing approaches, however, often focus primarily on improving attack success rates while overlooking the need for comprehensive test case coverage. Additionally, most of these methods are limited to single-turn red teaming, failing to capture the multi-turn dynamics of real-world human-machine interactions. To overcome these limitations, we propose **HARM** (**H**olistic **A**utomated **R**ed tea**M**ing), which scales up the diversity of test cases using a top-down approach based on an extensible, fine-grained risk taxonomy. Our method also leverages a novel fine-tuning strategy and reinforcement learning techniques to facilitate multi-turn adversarial probing in a human-like manner. Experimental results demonstrate that our framework enables a more systematic understanding of model vulnerabilities and offers more targeted guidance for the alignment process.

The technology of text-to-SQL has significantly enhanced the efficiency of accessing and manipulating databases. However, limited research has been conducted to study its vulnerabilities emerging from malicious user interaction. By proposing TrojanSQL, a backdoor-based SQL injection framework for text-to-SQL systems, we show how state-of-the-art text-to-SQL parsers can be easily misled to produce harmful SQL statements that can invalidate user queries or compromise sensitive information about the database. The study explores two specific injection attacks, namely boolean-based injection and union-based injection, which use different types of triggers to achieve distinct goals in compromising the parser. Experimental results demonstrate that both medium-sized models based on fine-tuning and LLM-based parsers using prompting techniques are vulnerable to this type of attack, with attack success rates as high as 99% and 89%, respectively. We hope that this study will raise more concerns about the potential security risks of building natural language interfaces to databases.