arXiv:2608.19741v5 Announce Type: replace Abstract: Recent agent benchmarks increasingly ground evaluation in executable environments, from code repair to web navigation, app APIs, and function calling. Yet completing consequential work beyond code requires more than producing a plausible response or valid tool call: agents must gather missing information over multiple turns, follow domain policies, coordinate dependent tools, and realize the correct persistent state transition without collateral effects. In this paper, we introduce Thinkingbox, a sandbox for tool-agent-user interaction that provides isolated MCP-compatible tool sessions, complete execution traces, and outcome evaluation over terminal backend state. Built on this sandbox, Thinkingbox-bench contains 507 policy-conditioned workflows across business scenarios, including retail, hospitality, auto insurance, neobank internal IT, and consulting IT/HR support. Each attempt is evaluated by task-specific executable checks that accept valid trajectories while rejecting wrong, missing, or extra effects; designated tasks additionally check required properties of the final response. Our experiments reveal that even the strongest proprietary and open-weight models show steep reliability drops: Claude Opus 5 falls from 66.50% pass@1 to 47.53% pass^20, and Kimi-K3 from 57.37% pass@1 to 17.60% pass^20. Moreover, many failed trials terminate cleanly after valid state-changing actions, so response- or tool-call-level signals poorly proxy end-to-end completion. Thinkingbox-bench reveals a large gap between occasionally finding a successful trajectory and reliably completing stateful business tasks. We release Thinkingbox, Thinkingbox-Bench, and Thinkingbox-integrated reinforcement learning framework.