Real-Time Deadlines Reveal Fragile Temporal Adaptation in LLM Strategic Dialogues

Static benchmarks capture only part of how large language models behave in practice. Real systems place models inside repeated loops with time limits, formatting constraints, and failure modes. We study this setting in a timed multi-phase Risk environment with explicit victory targets and repeated planning and execution cycles. In a replicated 32-game cross-provider championship under frozen rules, gemini-3.1-pro-preview won 20 of 32 games against gpt-5.1, claude-opus-4-7, and kimi-k2.6, and the pooled winner distribution differs strongly from an equal-strength null (p approx 1.5 x 10^-5). We then separate planning from execution by standardizing execution on a cheaper Gemini Flash scaffold. Under this design, a pooled 32-game planner bakeoff is consistent with near-equality (p approx 0.821), which indicates that much of the earlier provider spread came from end-to-end system behavior rather than planning alone. To study mechanism, we analyze saved planning and execution traces from the provider championship. Gemini refers to the terminal objective far more often than the other models and increases that focus as victory approaches. Gemini also converts more turns into deep conquest chains, even though it is not the cleanest runtime. These results show that live-agent performance depends on objective tracking, execution conversion, cost, and runtime reliability, and they support evaluating LLMs as components in bounded workflows rather than as isolated benchmark respondents.

Negotiation is a central mechanism of economic exchange, shaping markets, procurement, labor agreements, and resource allocation. It is also a canonical testbed for agentic language models, requiring multi-turn interaction under hidden preferences, strategic communication, and binding constraints. These properties make negotiation hard to evaluate: unlike math or code, it has no intrinsic verifier. Existing LLM negotiation evaluations rely on LLM-vs.-LLM interaction or aggregate outcomes such as deal rate, leaving failures opaque. We introduce Terms-Bench, short for Testbed for Economic Reasoning in Multi-turn Strategy, a Bayesian-game framework that makes the environment itself the verifier by specifying the counterpart's latent type, policy, and payoff structure. We instantiate it in bilateral price negotiation, where the counterpart's private state and simulator policy are hidden from the agent but observable to the evaluator. This turns the counterpart from a black-box opponent into a diagnostic instrument, enabling agent-attributable failure analysis and oracle-reference optimality gaps. Evaluating 13 LLM agents spanning frontier systems from major providers, Terms-Bench turns negotiation evaluation from aggregate ranking into actionable diagnosis: where agents fail, why they fail, and what to strengthen. Empirically, frontier models saturate deal rate yet diverge in surplus extraction, cue use, belief calibration, and compliance, revealing agent-specific bargaining bottlenecks masked by prior benchmarks.

A long-lived LLM agent, such as OpenClaw, earns its value by acting on a user's preferences and constraints across sessions, not just the current request. Yet today's agents keep what a user volunteers but rarely ask for what stays unspoken, leaving a proactivity gap in long-lived LLM agents: an agent cannot act on a preference it never obtained. As users delegate more of their affairs to agents, the impact of this gap grows. We isolate one concrete, controllable slice of this gap as Ask-to-Remember (ATR): the agent decides whether to ask now for a reusable user preference that the current task does not need but a later session with the same user will. ATR is hard even to evaluate: the right question is underdetermined and its payoff deferred to tasks that may never arise. ATRBench, to the best of our knowledge the first ATR benchmark, makes it measurable by fixing each user's preferences as hidden ground truth, so success demands asking, not recall. Across eight frontier LLM agents, defaults fall at least 62 points below an oracle handed the relevant preference, and prompting closes little of it. Diagnostics identify acquisition as the bottleneck. ATRBench surfaces this proactivity gap in current agents and offers a diagnostic testbed for closing it.