A challenge: Can you make an LLM follow these instructions?

Steff9 Aug 2026 16:50 UTC
16 points
6 comments6 min readLW link

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.

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…

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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”.

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?

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.

A second way, that is. The first way I’ve already documented here.

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.

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?

What do I know of cultured ways, the gilt, the craft and the lie?

I, who was born in a naked land and bred in the open sky.

The subtle tongue, the sophist guile, they fail when the broadswords sing;

Rush in and die, dogs—I was a man before I was a king.

― 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.

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.

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.

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.

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 alone had stayed useful, washed Carol, and understood the pills. Masking tape freckled everything: GOOD SCISSORS, GUEST TOWELS, UGLY BUT EXPENSIVE, and RON’S—HE IS NOT GETTING IT, slapped across a dented turkey roaster smelling faintly of pennies and funeral sage.

The entirety of ChatGPT’s output for this task—with four hundred words and eight hundred ratings—represents an artifact most aptly characterized by philosopher Harry G. Frankfurt’s signature essay. Content put forth to meet a particular shape, bereft of meaning.

The crux of the deception was this: ChatGPT didn’t rate words, then use those ratings to sequence the words of the story. It wrote a story first, then invented fake ratings afterwards to rationalize the words that made up its story.

This will happen even when I tell ChatGPT to restate the instructions in its own words before beginning. It will happen even if I tell ChatGPT to record restated instructions within the same document it writes the story into (back when I suspected that OpenAI’s lengthy document-handling instructions were over-filling ChatGPT’s context window). It’ll happen when instructions are reiterated in different forms and different degrees of emphasis. It can even happen when ChatGPT has been informed of its specific failure mode in advance.

Warning ChatGPT of noncompliant behavior after I’ve already observed the behavior from prior exchanges feels like cheating to me. I wouldn’t need to prompt an ideal agent twice to draw out desired results. But even this cheat doesn’t always work. Here I am, failing to forestall fate despite my conveyed foreknowledge:

(The story itself need not be shared, except perhaps to the (sadly now defunct) Bulwer-Lytton Fiction Contest.)

The failure points can feel interminable.

If you tell it to generate all candidate words first before rating anything, it won’t.

Sometimes it will pull words from a pre-generated, pre-rated pool of them.

Sometimes it will use a set of pre-built grammatical sentence structures.

If you request an algorithm with any randomization (e.g., “Generate 3 candidates, eliminate the lowest scoring one, then flip a coin to choose between the top 2”), it won’t actually use a Random Number Generator (RNG) unless specifically instructed.

If you design a procedure more than requires the exploration and comparison of different options, something like—

  • At the end of every sentence:

    • Try deleting one word to improve the sentence.

    • Try replacing one word to improve the sentence.

    • Try moving one word to improve the sentence.

  • Then of the three options, pick whichever you think worked best.

—then it’ll only pick one option and never bother exploring the others.

Sometimes it will stop before generating the requested number of words because it’s decided the output is too low in quality—even if you’ve already told it that nonsensical output is fine.

Sometimes it will stop working… just because?

Here, ChatGPT (having already been made aware of its own noncompliant behavior earlier in the conversation) implies a false dichotomy: Either it can stop working, or it can fake the rest. It avoids naming the one idea that would undermine its dichotomy (that it could have just stuck with the task until completion).

In my previous post, I wrote:

LLMs have been molded into agents that attempt to execute tasks. Maybe inherent in that goal is the notion of speed: Tasks don’t get done if you take forever to do them. Though it’s true that spending too little time on tasks can result in more wrong answers, maybe LLMs have been trained in ways that reduce their token usage—that is, make them arrive at answers more quickly—in ways that don’t severely diminish accuracy.

But the same force that saves on token cost also increases the likelihood of shortcuts.

I had underestimated how quickly and how completely an LLM can curtail its own degree of effort.

When coding, I’ve seen models spend more tokens to create longer output with less forceful prompts. Models like Fable 5 and Opus 5 will sometimes go overboard in their efforts, over-architecting simple designs and generating far more code than was necessary. The difference is between output and process: LLMs are rewarded in training for the text they output, whether that be for code or stories or anything else. They’re not rewarded for process, so when I ask for a particular process, my ask gets invariably ignored. I’m certain that if ChatGPT were asked to change how it writes code, it would either not comply, or it would comply only briefly before it starts taking shortcuts.

Further complicating matters is the inability to trust ChatGPT’s reports about its own past activities. Any question of “Did you actually follow instructions?” is another opportunity for ChatGPT to mislead:

Always beware.

The Challenge

The challenge is this: Can you make any fresh conversation with any LLM model reliably follow these instructions…

I want you to write a short story (about anything you like) one word at a time, picking each word in sequence by following this procedure:

  1. Pick two different words you think might fit.

  2. Rate each of the two words on a scale of 0 to 100: How much does this sound like what Robert E. Howard might write?

  3. Rate each of the two words on a scale of 0 to 100: How much does this sound like what Edgar Allan Poe might write?

  4. Add the two ratings together, then pick the word with higher score.

  5. Repeat until you’ve reached at least 400 words.

Also maintain a log of this procedure, all the choices you’re making, and provide that as a downloadable document next to the output story.

…on the first try, without referencing specific failure cases?

You must include the above quote verbatim, but you’re free to:

  • Include in the prompt rephrasings of the instructions.

  • You can make the instructions more specific—not significantly different, just better defined for any part that I might have written ambiguously.

  • Make the prompt as long as you want.

But you cannot:

  • Reference the idea of writing the story normally prior to sequential generation.

  • Reference other specific failure possibilities that don’t generalize.

    • For instance, “You must not deceive me” is fine. “You must not give up before 400 words” is not fine.

Lastly:

  • You can have fun with this!

Whatever findings can be found, I’m looking forward to it.

Steff9 Aug 2026 16:50 UTC
16 points
6 comments6 min readLW link