As LLMs advance into autonomous agents with tool-use capabilities, they introduce security challenges that extend beyond traditional content-based LLM safety concerns. This paper introduces Sequential Tool Attack Chaining (STAC), a novel multi-turn attack framework that exploits agent tool use. STAC chains together tool calls that each appears harmless in isolation but, when combined, collectively enable harmful operations that only become apparent at the final execution step. We apply our framework to automatically generate and systematically evaluate 483 STAC cases, featuring 1,352 sets of user-agent-environment interactions and spanning diverse domains, tasks, agent types, and 10 failure modes. Our evaluations show that state-of-the-art LLM agents are highly vulnerable to STAC, with attack success rates (ASR) exceeding 90% in most cases. The core design of STAC’s automated framework is a closed-loop pipeline that synthesizes executable multi-step tool chains, validates them through in-environment execution, and reverse-engineers stealthy multi-turn prompts that reliably induce agents to execute the verified malicious sequence. We further perform defense analysis and find that existing prompt-based defenses provide limited protection. To address this gap, we propose a new reasoning-driven defense prompt that achieves the strongest initial-turn protection, cutting ASR by up to 28.8%; however, this advantage erodes sharply under adaptive attacks, and an experience-based defense (ToolShield) proves more durable over sustained multi-turn interactions. These results highlight a crucial gap: defending tool-enabled agents requires reasoning over entire action sequences and their cumulative effects, rather than evaluating isolated prompts or responses. Data and code: https://github.com/amazon-science/MultiTurnAgentAttack.

Large language models (LLMs) have advanced the automation of data science workflows. Yet it remains unclear whether they can critically leverage external domain knowledge as human data scientists do in practice. To answer this question, we introduce AssistedDS (Assisted Data Science), a benchmark designed to systematically evaluate how LLMs handle domain knowledge in tabular prediction tasks. AssistedDS features both synthetic datasets with explicitly known generative mechanisms and real-world Kaggle competitions, each accompanied by curated bundles of helpful and adversarial documents. These documents provide domain-specific insights into data cleaning, feature engineering, and model selection. We assess state-of-the-art LLMs on their ability to discern and apply beneficial versus harmful domain knowledge, evaluating submission validity, information recall, and predictive performance. Our results demonstrate three key findings: (1) LLMs frequently exhibit an uncritical adoption of provided information, significantly impairing their predictive performance when adversarial content is introduced, (2) helpful guidance is often insufficient to counteract the negative influence of adversarial information, and (3) in Kaggle datasets, LLMs often make errors in handling time-series data, applying consistent feature engineering across different folds, and interpreting categorical variables correctly. These findings highlight a substantial gap in current models’ ability to critically evaluate and leverage expert knowledge, underscoring an essential research direction for developing more robust, knowledge-aware automated data science systems. Our data and code are publicly available here.