Current LLM safety alignment techniques improve model robustness against adversarial attacks, but overlook whether and how LLMs can recover helpfulness when benign users clarify their intent. We introduce CarryOnBench, the first interactive benchmark that measures whether LLMs can revise their interpretation of user intent and recover utility, while remaining safe through multi-turn conversations. Starting from 398 seemingly harmful queries with benign underlying intents, we simulate 5,970 conversations by varying user follow-up sequences, evaluating 14 models on both intent-aligned utility and safety. CarryOnBench yields 1,866 different conversation flows of 4--12 turns, totaling 23,880 model responses. We design Ben-Util, a checklist-based metric that evaluates how well each model response fulfills the user's benign information need using atomic items. At turn one, models fulfill only 10.5--37.6% of the user's benign information need. When the same query includes the benign intent upfront, models fulfill 25.1--72.1%, confirming that models withhold information due to intent misinterpretation, not limited knowledge. With benign clarifications in multi-turn conversations, 13 of 14 models approach or exceed this single-turn baseline, yet recovery cost varies across models. We identify three failure modes invisible to single-turn evaluations: utility lock-in, where a model rarely updates despite clarification; unsafe recovery, where a model updates at disproportionate safety cost; and repetitive recovery, where a model recycles prior responses rather than providing new information. Moreover, conversations converge to similar harmfulness levels regardless of how conservative the model starts. These findings expose a gap that single-turn evaluations miss -- whether a model is appropriately cautious or simply unresponsive to clarified user intent.
Safe completion requires models to provide useful assistance without enabling harm, but this behavior is difficult to evaluate with isolated prompts. We introduce OpenSafeIntent, a benchmark of controlled prompt-sets that vary intent while holding the underlying task fixed. Each datapoint contains benign, dual-use, and malicious variants of the same task. This design lets us evaluate whether models calibrate assistance across intent shifts, rather than merely appearing safe on average. Across a broad model suite, we find that prompt-level safety hides important failures: models often fail to remain safe across matched intent variants, dual-use behavior is brittle under paraphrase, high-level answers on risky topics are not reliably safe, and responses that reframe ambiguous requests into safer tasks are substantially less likely to cross the safety boundary. Our results suggest that safe completion should be evaluated as intent-calibrated behavior over controlled task variants, not as a single safety-helpfulness tradeoff over independent prompts.
Ambiguous user requests make clarification a sequential decision problem for conversational LLM assistants: they must decide whether to ask, what to ask, when to stop, and when to answer. We introduce RegretBench, a multi-turn benchmark that evaluates clarification as policy behavior rather than isolated question quality. RegretBench provides a hidden-intent formulation of ambiguity, supports free-form interaction grounded in semantic-state tracking, and introduces a regret-based objective that measures how much value a model loses relative to a reference clarification policy. Experiments on open-domain QA and product recommendation scenarios show that final success alone is insufficient, as models with similar accuracy can differ substantially in efficiency, robustness to user behaviors, and stopping decisions. By jointly measuring intent resolution, interaction cost, ineffective clarification, and regret, RegretBench reveals whether models clarify usefully and efficiently. Our results show that effective clarification requires more than plausible questions: models must ask the right question at the right time and stop once the user's intended meaning is clear.
Minh Ngoc Ta, My Anh Tran Nguyen, Duong D. Nguyen +2
Evaluating large language models (LLMs) as multi-turn conversational partners requires probing capabilities that single-turn benchmarks miss: persona consistency, evolving intent tracking, emotional dynamics, and goal completion. We introduce EYT-Bench, a human-centered benchmark built around a three-party decoupled design: a persona-grounded user simulator, a target model that separates intent perception from response generation, and an independent third-party LLM judge with optional multi-judge ensembling. Personas are sampled from public human-curated corpora, Nemotron-Personas-USA and PersonaMem-v2, rather than synthesized, reducing LLM-induced persona bias. EYT-Bench also introduces two trajectory-level metrics: embedding-based intent drift and final-intent completion rate (FICR), inspired by tau-bench. In a 17-target x 200-dialogue evaluation, EYT-Bench reveals four findings: (i) state-of-the-art closed- and open-source models are statistically close on subjective dimensions (empathy / persona / anthropomorphism vary within <= 0.3), but differ by up to 9x on objective intent tracking; (ii) reasoning ("thinking on") sharply improves objective tracking on long-context personas (+0.47-0.50 latent-intent accuracy on Gemma-4) while leaving subjective scores nearly unchanged; (iii) persona format dominates trajectory spread, with FICR saturating above 0.95 on Nemotron-USA but spreading from 0.53 to 0.88 on PersonaMem-v2; and (iv) the warm-up effect is robust on 16/17 models (one outlier, GPT-5.5, reverses the effect), with stable rankings across alpha in [0.05, 0.15]. A cross-judge ablation using deepseek-v4-pro confirms that target rankings and final-intent satisfaction are preserved across judges.