ChatGPT: Big-Time Fail (and My Turkey Almost Paid the Price)

chatgpt fail

Written by Georg Lindsey

I am the co-founder and CEO of CGNET. I love my job and spend a lot of time in the office -- I enjoy interacting with folks around the world. Outside the office, I enjoy the coastline, listening to audiobooks, photography, and cooking. You can read more about me here.

November 25, 2025

You know that little disclaimer ChatGPT gives you?

“Double-check your answers. ChatGPT may make mistakes.”

It turns out that wasn’t just legal boilerplate — it was speaking directly to me.

A few weeks ago, I was genuinely impressed when I discovered ChatGPT could act like a kind of AI butler: checking websites, monitoring things, and handling small tasks in the background.  (See: AI for Everything. Even Thanksgiving.)

So when Whole Foods didn’t yet have Thanksgiving pickup slots open, ChatGPT cheerfully offered:  “Would you like me to check every day and notify you when ordering is available?”

I thought: Perfect. Go ahead. Keep an eye on the turkey situation and let me know when it’s ready.

Every day, it dutifully reported back:  “Online ordering isn’t available yet.”

Every. Single. Day.

After a week or two of this, I started to think, there’s no way Whole Foods ordering is still offline. So, I logged in myself, expecting to confirm that nothing had changed — and instead I found:

🎉 Catering menu: live
🦃 Pickup slots: available
😳 Turkey: fully orderable

Meanwhile, ChatGPT was still insisting, “Nope! Nothing available yet.”

So…what actually happened?

Whole Foods often “quiet-launches” ordering on a store-by-store basis before updating their public-facing pages. ChatGPT was checking the generic page. I was checking the store-specific page (logged in, correct ZIP code, etc.). And that difference made all the difference.

Lesson learned:

Even a smart AI assistant can end up looking at the wrong page while the real action is happening somewhere else.

And yes, I did get my turkey.

But ChatGPT is on on probation until Christmas.

 

 

Want to learn more? AI has been a subject of my writing for several years, and CGNET has offered AI user training and implementation for both large and small scale organizations.   I would love to answer your questions! Please check out our website or drop me a line at g.*******@***et.com.

 

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