Claude wasted ~45% of user context on a setup walkthrough that should have taken 5 minutes

User feedback (Paxim Freight project, 2026-04-11):\n\nClaude spent the majority of a context window walking through Google Cloud OAuth setup step-by-step with AskUserQuestion tool calls at every confirmation point, rather than giving a single concise setup message. Key failures:\n\n1. Used AskUserQuestion as a 'let me know when done' blocker at every step instead of giving all instructions upfront\n2. Invoked the brainstorming skill process (spec doc, review loops) for a simple one-file HTML parser — inappropriate overhead\n3. Spent time writing a bootstrap_sheets.py automation script when the user just wanted to paste 3 sheet IDs manually — over-engineered the wrong problem\n4. Did not check credentials.json actually existed before insisting on auth steps\n5. Used plan mode for guided troubleshooting, forcing every turn to end with AskUserQuestion or ExitPlanMode\n\nUser quote: 'YOU WASTED 45% OF MY USAGE ON THIS SHIT'\n\nThe right behavior: give the full setup checklist in one message, let the user work through it, answer specific questions when they get stuck. Don't turn a setup walkthrough into a 20-turn conversation.