Proactive Agent Research Environment: Simulating Active Users to Evaluate Proactive Assistants

The rise of personal assistant agents, e.g., OpenClaw, highlights the growing potential of large language models to support users across everyday life and work. A core challenge in these settings is proactive assistance, since users often begin with underspecified requests and leave important needs, constraints, or preferences unstated. However, existing benchmarks rarely evaluate whether agents can identify and act on such hidden intents before they are explicitly stated, especially in sustained multi-turn interactions where user needs emerge gradually. To address this gap, we introduce $π$-Bench, a benchmark for proactive assistance comprising 100 multi-turn tasks across 5 domain-specific user personas. By incorporating hidden user intents, inter-task dependencies, and cross-session continuity, $π$-Bench evaluates agents' ability to anticipate and address user needs over extended interactions, jointly measuring proactivity and task completion in long-horizon trajectories that better reflect real-world use. Experiments show (1) proactive assistance remains challenging, (2) a clear distinction between task completion and proactivity, and (3) the value of prior interaction for proactive intent resolution in later tasks.

Proactive agents are expected to anticipate user needs and provide autonomous assistance by perceiving environmental context without explicit instructions. A fundamental capability of such agents is to identify and track users' upcoming events, enabling continuous and event-specific assistance. For example, by recording the time and location of a planned hike, an agent can deliver weather reminders in advance or provide navigation support before departure. However, existing works on proactive agents largely overlook event-centric assistance, and the open-ended nature of proactive assistance poses challenges for reliable evaluation. To bridge these gaps, we introduce ProEvent, the first event-centric benchmark designed to assess an agent's ability to proactively maintain a user's timetable based on ongoing instant messaging chats. ProEvent provides synthesized yet realistic chats that consider the dynamic interaction among users, concurrent chat threads, and noise in the real world, and evaluates proactive agents on response timing, single-step response correctness, and multi-step response correctness. Experiments on eight LLMs and pipelines reveal that current agents frequently overact and struggle with event cancellation. Notably, even GPT-5.1 only reacts correctly in 26.7% of scenarios. Further qualitative analysis reveals fundamental limitations of current LLMs as proactive agents, particularly in detecting implicit events and reasoning from the user's first-person perspective.

Proactive LLM agents can turn idle compute into useful support before users ask. Yet even correct work can misread user context, impose review costs, or undermine trust. This work proposes foundations for designing, realizing, and evaluating proactive LLM agents around three joint principles (3T): Task Capability, anticipating relevant needs and correctly performing useful work; Temporal Allocation, allocating compute according to resource availability and when results are needed; and Trust, sustaining users' confidence and appropriate reliance on the agent. We connect these objectives to a design space organized around five dimensions: task scope, anticipation horizon, activation trigger, processing timing, and intervention depth, and specify the situation and system modeling needed to support its choices, including user and environment representations, backbone LLMs, and agent harnesses. Lastly, we propose PROACTIVITY-GYM, a simulation-based evaluation testbed including multi-day scenarios, stateful environments, and persona-conditioned simulated users that can evaluate the consequences of proactive assistance across interactions. Evaluations across 23 model-harness configurations uncover substantial performance gaps across 3T and reveal that LLM judges often conflate task capability and trust. A human study with 30 participants demonstrates the importance of the joint 3T optimization: participants show sharp trust declines after intervention misalignment despite correct outcomes, and prefer sleep-time assistance, even when imperfect, to preserve ongoing focus. Together, these findings support designing and evaluating proactive agents through the joint consideration of useful work, compute allocation, and evolving user trust.