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The ask_user tool used AskUserInterrupt(BaseException) for mid-turn blocking, creating heavy coupling across runner, loop, and session management. The model now asks questions naturally in response text, the turn ends normally, and the user's next message starts a new turn with session history providing continuity. Removed: - nanobot/agent/tools/ask.py (tool, interrupt, helpers) - tests/agent/test_ask_user.py - webui/src/components/thread/AskUserPrompt.tsx - AskUserInterrupt handling in runner.py - Dual-path message building in loop.py - Pending ask detection via history scanning - button_prompt/buttons emission in WebSocket channel - ask_user references in Slack channel docstrings Preserved (MessageTool uses these independently): - OutboundMessage.buttons field - Channel button rendering (Telegram, Slack, WebSocket)