ChatGPT Work fought Uber support through two rejections and won $95.46 in credits
nickbaumann_ · x · 2026-08-24
After two consecutive Uber Eats orders were cancelled (45 min wasted each), nickbaumann told ChatGPT Work to get compensation and not back down. The full timeline:
- 6:19 PM: AI opens a support case asking for $20 in Uber Cash
- Two agents refuse: AI rejects the resolution, escalates to a supervisor, and tries promos, fee waivers, and Uber One extensions
- Second order cancelled: AI opens a combined Uber One case, raises the ask to $30, and files a written complaint with timestamps, order IDs and membership details
- AI sets background checks across both cases, Gmail, and the Uber Wallet
- 7:50 PM: a specialist approves $95.46 total in Uber Cash; 8:44 PM: AI verifies the credit, marks the goal complete, and shuts down its own follow-up automation
Total human effort: 15 minutes active plus 2.5 hours of background work. The author credits Uber for ultimately making it right.
More from Fun
- SF mansions are like bitcoin: AI wealth and the 'mansion shortage' joke — matt_slotnick · 2026-10-16
- AI-written cold emails hit a wall: Pragmatic Engineer's reply gets templated AI response — marktenenholtz · 2026-10-16
- Higgsfield teases Kling 4.0 rollout with a monkey-driven demo video — azed_ai · 2026-10-16
- 'Dropping a 3,000-line PR twenty minutes after ticket assignment' — AI coding meme goes viral — facontidavide · 2026-10-16
- 'Don't Date Paid-Tier AI Models': The Power Imbalance Joke Going Around — birchlse · 2026-10-16
- One word and ChatGPT went full bro-mode: Reddit post shows guardrail oddly breaking — justalexoki · 2026-10-16