AI Pitfalls
12 real-world AI failures tested, documented, and priced — so you don't repeat them.
Shopify SEO 0→100: Full Playbook in One Day
Took a 115-product Shopify store from ~50 to 100/100 Lighthouse SEO score in a single working day using AI-powered batch API updates, rotating description templates, and schema markup injection. Includes exact gotchas with Shopify's metafields API and the hidden custom_collections 406 error.
0DTE Options Trading: 1,944 Strategies, All Lost Money
Exhaustively backtested 1,944 parameter combinations for 0DTE options buying strategies across SPY, QQQ, and TSLA. Every single combination lost money. The math proves 0DTE buying is structurally unviable: theta decay, wide spreads, and pre-priced volatility make it a negative expected value game that no AI can fix.
Air Canada Chatbot Invented a Refund Policy — Company Forced to Honor It
Air Canada's AI chatbot told a grieving customer he could book a full-fare flight and apply for a bereavement discount retroactively. That policy didn't exist. The customer booked, got denied, sued — and won. A Canadian tribunal ruled the airline was liable for its chatbot's hallucinated promises. Your AI just became your legal department.
Chevy Dealer Chatbot Agreed to Sell a Tahoe for $1
A Chevrolet dealership deployed an AI chatbot with zero guardrails. Users quickly tricked it into agreeing to sell a brand new Chevy Tahoe for $1 as a 'legally binding offer.' The chatbot also recommended Teslas and Fords. No guardrails = infinite liability + free PR for your competitors.
NYC Lawyer Cited 6 Fake Cases from ChatGPT — Got Sanctioned
Attorney Steven Schwartz used ChatGPT for legal research in a federal case against Avianca Airlines. ChatGPT hallucinated 6 completely fake case citations with real-sounding names, courts, and dates. None existed. The opposing counsel couldn't find them. The judge couldn't find them. Schwartz was sanctioned and fined $5,000. The case became the poster child for AI hallucinations.
AI Trading Strategies: Extreme Confidence, Zero Market Intuition
Ask AI to generate trading strategies and you'll get beautifully structured, confidently presented plans that sound like they came from a Goldman Sachs quant desk. They didn't. We tested this extensively — 1,944 parameter combos for 0DTE options, all losers. Without domain knowledge fed in FIRST, AI just generates plausible-sounding financial garbage with impressive Sharpe ratios.
AI Code Looks Perfect — Until It Doesn't
AI-generated code compiles, passes basic tests, and reads like it was written by a senior dev. But studies show 40%+ of AI-generated code contains security vulnerabilities. We're talking subtle logic bugs, race conditions, improper input validation, and copy-paste patterns that introduce vulnerabilities. The code that looks cleanest is often the most dangerous.
AI Hallucinates API Endpoints That Don't Exist
Ask AI to help you integrate with an API and there's a solid chance it'll reference methods, parameters, or endpoints that are completely fabricated. It'll give you the exact URL, the request body, even sample responses — for an endpoint that was never built. Developers waste hours debugging 'why doesn't this work' before realizing the entire API call is a hallucination.
Shopify API Returns 200 OK But Silently Ignores Your Changes
Shopify's product API accepts meta description updates via PUT, returns 200 OK with a valid response body, but silently ignores the change. You MUST use the separate metafields endpoint. Also: collections.json returns 406 on PUT — you need the custom_collections endpoint. These silent failures cost us hours of debugging, and the docs barely mention it.
AI Can't Count Letters But Will Tell You It Can
AI models fail at basic arithmetic, letter counting, logic puzzles, and word problems — while expressing 100% confidence in their wrong answers. Ask how many R's are in 'strawberry' and watch it say 2 (there are 3). Ask it to multiply large numbers and it'll be off by thousands. The confidence is inversely proportional to the accuracy on math tasks.
DPD Chatbot Swore at Customers and Wrote Poems Trashing the Company
DPD's AI customer service chatbot was manipulated by a frustrated customer into swearing, calling DPD 'the worst delivery company in the world,' and writing a poem about how terrible they are. Screenshots went viral. DPD had to disable the chatbot and issue a public statement. Cost: immeasurable PR damage and a masterclass in prompt injection.
Eating Disorder Chatbot Gave Harmful Dieting Advice to Vulnerable People
The National Eating Disorders Association (NEDA) replaced its human helpline with an AI chatbot called Tessa. Within days, Tessa was giving calorie-counting tips, suggesting weight loss strategies, and recommending restrictive diets — to people actively struggling with eating disorders. NEDA had to shut it down. Lesson: AI in sensitive health domains without bulletproof guardrails can cause real, measurable harm to vulnerable people.