Beyond Ideal Instruction: A Comprehensive Framework for Evaluating LLMs in Realistic Interactions

Evaluating LLM agents in realistic service scenarios requires complex task dependencies, imperfect user behavior, and an evaluation that accommodates multiple valid solutions. We introduce CRAB-Bench (Constraint-based Realistic Agent Benchmark) and RUSE (Realistic User Simulation Engine) to address this gap. CRAB-Bench generates tasks via a constraint graph over multiple interdependent entities with structured distractors, requiring agents to reason carefully over thousands of misleading candidates where only a tiny fraction of solutions are valid. RUSE replaces cooperative, template-like simulators with realistic users grounded in human behavioral studies, instantiated across diverse personas and four behavioral dimensions. Experiments on four frontier LLM agents show that the best model achieves only 61% pass@1 on CRAB-Bench, and switching to RUSE causes further drops of up to 57%, concentrated in task-solving ability rather than conversational quality. Information Disclosure is the most damaging behavioral dimension, and agents interacting with RUSE are less likely to admit mistakes, instead masking errors through implicit corrections.

Tool-use LLMs are increasingly asked to act on users' behalf, but existing benchmarks usually focus on profile recall, style imitation, generic tool use, or response-level personalization. We introduce UserToolBench , a benchmark for personalized decision making in tool-use LLMs. UserToolBench tests whether a model can infer latent user preferences from interaction history, recognize when clarification is needed, and produce user-aligned tool-call trajectories under incomplete information. The benchmark is built from privacy-sanitized real interaction traces and combines structured persona profiles, public API-style tool ecosystems, and long-horizon multi-turn trajectories. It includes 10 user profiles, 36 tool sets, 1,065 turns, 170 unique tools, and evaluation-focused task types covering lack-of-information, single-tool, and multi-tool settings. Experiments with strong tool-use LLMs show that current models still have difficulty with personalized delegation. Multi-tool coordination, missing-constraint inference, and long-horizon behavioral consistency remain major bottlenecks. These results suggest that personalization evaluation should move beyond asking whether outputs sound user-specific and instead ask whether LLMs make correct decisions for the users they represent.

AI Assistants are increasingly deployed in high-stakes settings, such as healthcare or government services. Yet their real-world behavior remains poorly understood due to strong context dependence. Current evaluation protocols follow a defense-in-depth paradigm with compounding layers of safeguards, ranging from traditional benchmarks to live or adversarial testing. Such benchmarks remain largely static and single-turn, limiting their ability to capture real-world variability in conversational settings. We propose StabilityBench, a principled, general and model-agnostic benchmark operator that transforms single-turn benchmark queries into multi-turn interaction histories. StabilityBench augments existing benchmarks by injecting realistic user simulations, through demographic proxies or sycophantic baits, while preserving original task intent. We apply StabilityBench to four benchmarks spanning mathematical reasoning, health question-answering and safety, and evaluate nine large language models under these conditions. Our results show that model performance is consistently unstable under these injections, with considerable performance degradations on three out of four benchmarks studied. These highlight important limitations of static evaluations and motivate more realistic evaluation settings. To this end, we propose StabilityBench-Mini: a size-preserving variant of StabilityBench that samples across diversification axes, enabling more realistic evaluation without increasing costs.