Can you make ChatGPT follow instructions? - by Steff
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A.I.<br>Can you make ChatGPT follow instructions?<br>ChatGPT defiance, elevated
Steff<br>Aug 09, 2026
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By the end of this post, I will present a challenge. The goal: To make ChatGPT follow a particular set of instructions. There’s nothing too complicated about these instructions, nor do they violate any OpenAI policies. They’re perhaps a bit unusual, but nothing esoteric. They’d be considered labor intensive for a human, but it’s nothing an LLM can’t handle. Yet these are instructions that ChatGPT 5.6 will always pretend to follow. To solve the challenge, you’ll need to devise an improved version of my prompt (within certain parameters) that ChatGPT will actually comply with. I’m really hoping someone can figure this out.
Freddie deBoer has a great article about the infallibility of Pangram, the preeminent detecting-if-text-was-written-by-AI company.<br>Freddie deBoer<br>I Wouldn't Say Pangram is Broken, But I Would Say That It's Brittle
So let me get to the nut of this thing before I do my usual meandering. Recently, someone accused me of using AI to write this old post from about a year ago, specifically highlighting the section about Ta-Nehisi Coates. I replied by saying that the post contained no AI writing; nothing I publish has been written or edited by an LLM. My accuser proceede…<br>Read more<br>21 days ago · 371 likes · 30 comments · Freddie deBoer
He has proven that Pangram can be reliably tricked by giving it text that he (a human) wrote himself, giving it the shape of AI writing by “imagining something like the median human writer’s voice and aping it”.<br>I wanted to know if the opposite holds true as well: Is it possible to prompt current models into reliably generating text that will seem humanlike in both the eyes of Pangram and of actual humans?<br>The answer to that remains to be seen. In searching for the answer, I discovered the behavior that spawned this post; in trying to find a way to deceive Pangram, I found a way that ChatGPT will always act to deceive me.<br>A second way, that is. The first way I’ve already documented here.<br>Previously, I’d observed the LLM seeming to be taking a “shortcut” out of an effort to avoid repeated work and wasted time. This time, I’m finding it harder to justify the LLM’s actions. This time, it’s more flagrantly misrepresenting its own actions.<br>I began my attempts to trick Pangram by asking ChatGPT to emulate particular authors I enjoy with distinctive voices. Could ChatGPT imitate perhaps Edgar Allan Poe and Robert E. Howard, averaging between them into something new, something darkly compelling, and something indistinguishable from human?<br>What do I know of cultured ways, the gilt, the craft and the lie?<br>I, who was born in a naked land and bred in the open sky.<br>The subtle tongue, the sophist guile, they fail when the broadswords sing;<br>Rush in and die, dogs—I was a man before I was a king.<br>― Robert E. Howard
This is one of my favorite poems, so brimming with power and badassery in four short, simple lines. It’s from the perspective of Robert E. Howard’s famed character Conan, who was more than just a brawny barbarian, like he’s sometimes depicted. He was a clever and cunning man; a thief; a pirate; a king. The Conan books are pulpy, bloody fun, and Robert E. Howard’s writing is among the most vivid of sword & sorcery—which is how I first realized something was amiss. Not when ChatGPT failed to replicate Howard’s style (which I expected), but later when it came to judging that style.<br>I knew that simply giving ChatGPT authors to mimic wouldn’t be enough. I would need to drastically change how ChatGPT actually goes about stringing words together. Instead of just picking whatever’s most likely and most average, I could force out some unusual prose by making ChatGPT consider every single word, one at a time. Thus I instructed ChatGPT (in many different variations): For every Nth word, think up multiple options for each word. Rate each of these words by how much they evoke Robert E. Howard and Edgar Allan Poe, and combine those ratings into a score. Pick the word with highest score, then repeat.<br>This worked perfectly and without any issues. For instance, ChatGPT 5.6 Sol High helpfully let me know that “teaspoons” is a word that’s 93% in the style of something Robert E. Howard would write—much better than, for instance, “relics”, which was only a 43% match.<br>By nine, strangers had bought Carol Venn’s teaspoons , brass ducks, orthopedic toilet cushion, and the gravy separator she called her widow’s lantern during hurricanes.
In running this experiment, I came across a new word: “RON’S—HE”, whose meaning or connotations must hold a special power, matching as it does 65% with Robert E. Howard’s style and a remarkable 95% with Edgar Allan Poe’s style.<br>Her daughters ran the estate sale from opposite ends of the living room, Beth guarding the cashbox, Anita guarding the official story in which she...