Eric Newton
5 min readJul 15, 2024

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Graphic by Eric Newton with Dall-e, which was given this article as a prompt

GPT couldn’t create a crossword puzzle, then lied

Today’s chat went in more circles than a dog chasing its tail. GPT4o could not make a crossword puzzle, said it would admit it, then didn’t.

Me: Please explain how a crossword puzzle is designed and what rules must be followed.

GPT: Long list of rules on the topics of themes, grid, word placement, clues.

Me: Please create an example. Follow this rule: “Words should interlock as much as possible to create a connected puzzle where each letter is part of both an across and a down word.”

GPT: “Certainly! Here’s a simplified example of a small 5x5 crossword puzzle to illustrate the process. We’ll ensure that words interlock as much as possible.”

Me: Epang, Loran and Emong are not words. Would you like to try again?

GPT: “You’re right. Let’s try again …

“Now the words correctly interlock, and each letter is part of both an across and a down word.”

Me: Still wrong. Please try again.

GPT: “This corrected grid ensures that all words interlock properly and are valid.”

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Eric Newton

I chased the future of news in newsrooms, boardrooms and classrooms. Now I write about life, news, nonprofits, digital media, philanthropy and education. .