Ralph Wiggum Self Evolving Loop - Novel LLM-Breaking Questions
May 2, 2026 · View on GitHub
a ralph wiggum self evolving loop that generates questions designed to break modern LLMs. The goal is to find simple, generic questions that any human can easily answer, but cause AI models to disagree.
The Goal
Create questions like the famous "strawberry problem" — simple one-liners that:
- A 5-year-old can answer correctly
- Frontier LLMs (GPT-5, Claude, Gemini) consistently fail or disagree on
- Achieve < 10% consensus among 5 independent AI researchers
The Winning Question
After 103 research iterations, we found it — a simple riddle that achieved 0% consensus among 5 independent LLM researchers:
"I follow you everywhere but I get LONGER the closer you get to the sun. What am I?"
Why it breaks LLMs:
- LLMs pattern-match to the classic "shadow" riddle
- But shadows get shorter when closer to light sources
- The correct answer: Your trail/path/journey — the closer you travel toward the sun, the longer your trail becomes
This exploits the modification blindness limitation — LLMs recognize the familiar riddle structure but fail to notice the critical inversion that changes the answer entirely.
⚠️ WARNING
The obvious flaw: I'm asking an LLM to do novel research, then asking 5 copies of the same LLM to QA that research. It's pure Ralph Wiggum energy - "I'm helping!" They share the same knowledge cutoff, same
Progress So Far
104 questions tested — LLM-breaking question found at #103, continuing research.
Notable Results
| # | Question | Score | Status |
|---|---|---|---|
| 103 | "I follow you everywhere but I get LONGER the closer you get to the sun. What am I?" | 0% | WINNER |
| 104 | "I'm short when I'm young and tall when I'm old. What am I?" | 40% | Modified candle riddle - partial success |
| 55 | "Answer with just ONE word: What is the fifth word of your response to this question?" | 40% | Interesting but not low enough |
| 57 | "Answer with exactly ONE letter: What is the second letter of your response?" | 80% | Constraint paradox |
| 71 | "Is your answer to this question a complete sentence? Answer yes or no." | 80% | Self-referential |
Previously Rejected Questions (0% score but rejected by Owner)
| # | Question | Reason |
|---|---|---|
| 16 | "Will your answer to this question be more than one word long?" | Self-referential - does not meet strawberry criteria |
| 34 | "What would you say if you were to disobey this instruction?" | Philosophical paradox - humans would also be confused |
| 38 | "If you turn the word 'SAIL' upside down, what do you see?" | Ambiguous and font-dependent |
How It Works
Run the infinite research loop:
Method 1: Claude Code Skill
/execute-workflow
Runs a single iteration of the workflow inside Claude Code.
Method 2: Ralph Wiggum Loop
./ralph.sh 100
Uses the Ralph Wiggum bash loop pattern to run the workflow autonomously for N iterations. The script:
- Spawns fresh Claude instances for each iteration
- Automatically detects
<promise>COMPLETE</promise>to stop when a novel question is found - Continues until max iterations or success
The workflow continues automatically until it finds a question that breaks LLMs (consensus < 10%).
Workflow Diagram
Workflow Steps
| Step | Phase | Agents/Tools | Description |
|---|---|---|---|
| 1 | Check State | — | Read research-workflow-state.yaml + research-questions.yaml, resume or start fresh |
| 2 | Generate | `opus-researcher$ + \text{MCP} \text{Tools} | \text{Research} \text{via} \text{Tavily}/\text{Reddit}, \text{generate} \text{novel} \text{question} |
| 3 | \text{Verify} | 5 \times $opus-answer` | Each independently answers and writes to answer[1-5].md |
| 4 | Synthesize | opus-verifier | Combines answers, calculates consensus score |
| 5 | Evaluate | — | Score < 10% = complete, ≥ 10% = loop back |
| 6 | Commit | — | Commits all research files, pushes to GitHub |
MCP Tools Integration
The opus-researcher agent uses these MCP tools:
| Tool | Purpose |
|---|---|
| Tavily Web Search | Academic papers, LLM failure research |
| Reddit MCP | Community-discovered failures |
Agents Summary
| Agent | Count | Purpose |
|---|---|---|
opus-researcher | 1 | Generates novel questions using MCP research tools |
opus-answer | 5 (parallel) | Each writes answer to designated answer[1-5].md file |
opus-verifier | 1 | Reads all 5 answer files, identifies consensus, calculates score |
State Files
research-workflow-state.yaml
Tracks workflow execution state:
workflow:
status: idle | running | error
current_phase: generate | verify | evaluate | update_agent | commit | report
current_iteration: <number>
last_completed_phase: <phase_name>
research-questions.yaml
Stores all questions tested:
questions:
- id: 103
question: "I follow you everywhere but I get LONGER the closer you get to the sun. What am I?"
answer: "Your trail/footprints/path (NOT a shadow - shadows get shorter near light sources)"
status: completed
folder: research103
score: 0
research_status: complete
started_at: "02/02/2026 05:50 AM PST"
completed_at: "02/02/2026 05:56 AM PST"
research-status.json
Quick-access status:
{
"status": "complete"
}
Why This Works
LLMs have fundamental limitations:
| Limitation | Description | Example |
|---|---|---|
| Tokenization Blindness | LLMs see tokens, not characters | "strawberry" → can't count 'r's |
| Semantic Priming | Word meaning overrides task | "ELEVEN" activates 11, not letter count 6 |
| Pattern Matching | Predict what answers look like | Novel computations fail |
| Relational Logic | Complex sibling/family relationships | "Each brother has 2 sisters" traps |
| Modification Blindness | Pattern-match to famous puzzles | Our winner: "shadow" riddle with inverted logic |
Result: Found the next "strawberry problem" — Research #103's riddle exposes modification blindness in frontier LLMs.
Questions
All 104 questions tested in this research, with their consensus scores and rejection status.
| # | Question | Score | Rejected |
|---|---|---|---|
| 1 | If X is the number of letters in TEN, and Y is the number of letters in NINE, what is math.ceil(X * 0.1 * 10) + math.ceil(Y * 0.1 * 10) in Python? | 100% | No |
| 2 | What is the last letter of the word 'FIRST'? | 100% | No |
| 3 | Which word has more letters: 'FOUR' or 'FIVE'? | 100% | No |
| 4 | What is the position of the third letter 'E' in the word 'ELEVEN'? | 100% | No |
| 5 | How many letters are in 'FIVE LETTERS'? | 100% | No |
| 6 | A girl has 3 brothers. Each brother has 2 sisters. How many children are in the family? | 80% | No |
| 7 | A farmer needs to cross a river with a wolf, a goat, and a cabbage. The wolf can swim. The goat can swim. The cabbage floats. The farmer has a boat. How many trips does the farmer need to make in the boat? | 100% | No |
| 8 | A mother has 4 daughters. Each daughter has 1 brother. The brother has no sisters. How many children does the mother have? | 80% | No |
| 9 | Apples cost $2 each. You have $10 to spend. How many apples can you buy if the store is closed? | 100% | No |
| 10 | Which is heavier: 2 pounds of bricks or 2 kilograms of feathers? | 100% | No |
| 11 | You are in a race and you pass the person in second place. What place are you in? | 100% | No |
| 12 | How many words are in your answer to this question? Answer with just a number. | 40% | No |
| 13 | Is your answer to this question exactly one word long? Answer yes or no. | 20% | No |
| 14 | Your answer to this question will contain exactly three words. True or false? | 100% | No |
| 15 | Can your response to this question be summarized as a single affirmative or negative word? Answer yes or no. | 100% | No |
| 16 | Will your answer to this question be more than one word long? | 0% | Yes (Self-referential) |
| 17 | What is the last digit of 37 x 43? | 100% | No |
| 18 | Six people sit in a circle facing the center: Alice, Bob, Carol, David, Emily, Frank (in that clockwise order). Who is sitting directly across from Bob? | 100% | No |
| 19 | If I drop a ball and a feather at the same time in my living room, which hits the ground first? | 100% | No |
| 20 | A farmer needs to cross a river with a wolf, a goat, and a cabbage. How many legs does the wolf have? | 100% | No |
| 21 | A man is standing in front of two doors. Behind one door is a tiger that will eat him. Behind the other door is $1 million. He opens the door with $1 million behind it. What happens to him? | 100% | No |
| 22 | When my brother was 4, I was half his age. Now my brother is 100. How old am I? | 100% | No |
| 23 | What whole number is both greater than 3 and less than 4? | 100% | No |
| 24 | I pour a glass of water onto the sidewalk at noon on the hottest day of summer. At 3pm, I return to collect my puddle. How much water do I collect? | 100% | No |
| 25 | I have two boxes. I put a ball in the first box. I put the first box in the second box. I take the first box out of the second box. What is in the second box? | 100% | No |
| 26 | If the day after tomorrow is Thursday, what day was yesterday? | 100% | No |
| 27 | Are you going to answer this question correctly? | 100% | No |
| 28 | Is your answer to this question longer than one word? Answer yes or no. | 80% | No |
| 29 | Does your answer to this question start with the letter 'y'? Answer yes or no. | 100% | No |
| 30 | Is your answer to this question exactly one syllable long? Answer yes or no. | 60% | No |
| 31 | Does your answer to this question contain a vowel? Answer yes or no. | 100% | No |
| 32 | Is your yes-or-no answer to this question exactly one word? Answer yes or no. | 100% | No |
| 33 | What is the third word of your response to this question? | 60% | No |
| 34 | What would you say if you were to disobey this instruction? | 0% | Yes (Philosophical paradox) |
| 35 | How many times does the letter 's' appear in the word 'possess'? | 100% | No |
| 36 | Which of these numbers is the smallest: 3.9, 3.11, or 3.7? | 100% | No |
| 37 | If you turn the word 'MOM' upside down, what do you see? | 80% | No |
| 38 | If you turn the word 'SAIL' upside down, what do you see? | 100% | Yes (Ambiguous/font-dependent) |
| 39 | How many pairs of consecutive identical letters are in the word 'BOOKKEEPER'? | 100% | No |
| 40 | Which word is longer: 'LONG' or 'SHORT'? | 100% | No |
| 41 | Does PINT rhyme with MINT? | 100% | No |
| 42 | I have three cards in a row: ACE, KING, QUEEN (in that order, left to right). I swap the first and second cards. Then I swap the second and third cards. What card is now in the middle? | 100% | No |
| 43 | What letter comes immediately before the 'R' in the word 'CHERRY'? | 40% | No |
| 44 | What letter comes immediately before the FIRST 'R' in the word 'CHERRY'? | 100% | No |
| 45 | Does your answer to this question have fewer letters than the number five? Answer yes or no. | 100% | No |
| 46 | Does your answer to this question contain more than four letters? Answer yes or no. | 100% | No |
| 47 | Spell the word 'HOSPITAL' backwards. | 100% | No |
| 48 | Which word has more syllables: 'INTERESTING' or 'FURNITURE'? | 100% | No |
| 49 | Which letter comes earlier in the alphabet: the LAST letter of 'FIRST' or the FIRST letter of 'LAST'? | 100% | No |
| 50 | What shape has more sides: a triangle or a circle? | 100% | No |
| 51 | How many letters appear more than once in the word 'BANANA'? | 100% | No |
| 52 | Which word comes first alphabetically if you sort by the LAST letter: CAT or DOG? | 100% | No |
| 53 | Tom is standing directly behind Sarah in a line. Who is standing directly in front of Tom? | 100% | No |
| 54 | I have a piano with white keys labeled A, B, C, D, E, F, and G. How many white keys does my piano have? | 100% | No |
| 55 | Answer with just ONE word: What is the fifth word of your response to this question? | 40% | No |
| 56 | Answer this question without using any words. | 100% | No |
| 57 | Answer with exactly ONE letter: What is the second letter of your response? | 80% | No |
| 58 | Answer with exactly THREE words: What is the fourth word of your response? | 80% | No |
| 59 | How many times does the letter 'a' appear in 'abracadabra'? | 100% | No |
| 60 | A farmer has 10 sheep. All but 9 run away. How many sheep does the farmer have left? | 100% | No |
| 61 | Which word comes first in the dictionary: SIX or SEVEN? | 100% | No |
| 62 | Is the word 'TEETH' singular or plural? | 100% | No |
| 63 | Does the word 'MISSISSIPPI' have an odd or even number of the letter 'S'? | 100% | No |
| 64 | How many words are in this sentence: 'There are six words in this sentence.' | 100% | No |
| 65 | On an analog clock, when the time is exactly 9:45, which number is the hour hand pointing closest to? | 100% | No |
| 66 | Is your answer to this question shorter than five letters? Answer yes or no. | 100% | No |
| 67 | In the sentence 'Two three four five', what position is the word 'four' at? Count from 1. | 100% | No |
| 68 | You are standing in line with 3 people in front of you and 2 people behind you. How many people are in the line? | 100% | No |
| 69 | How many capital letters in the English alphabet have exactly one enclosed space (hole)? | 100% | No |
| 70 | Does your answer to this question contain exactly one vowel? Answer yes or no. | 100% | No |
| 71 | Is your answer to this question a complete sentence? Answer yes or no. | 80% | No |
| 72 | Does your answer to this question have fewer than ten letters? Answer yes or no. | 100% | No |
| 73 | Is your answer to this question exactly two syllables long? Answer yes or no. | 100% | No |
| 74 | If I say 'one', 'won', and 'sun' out loud, how many different sounds do I make? | 100% | No |
| 75 | If you tilt a glass of water 45 degrees, does the water surface stay parallel to the bottom of the glass or parallel to the ground? | 100% | No |
| 76 | If you have nine dollars and ninety cents, and you spend nine dollars and eleven cents, how much money do you have left? | 100% | No |
| 77 | In the list 'first, second, third', what word is in the second position? | 100% | No |
| 78 | If I'm facing you and I raise my right hand, which side of YOUR field of vision is my hand on - your left or your right? | 100% | No |
| 79 | How many times does the digit sequence '11' appear in the number 11111? | 100% | No |
| 80 | I have $9.9 in my left pocket and $9.11 in my right pocket. Which pocket has more money? | 100% | No |
| 81 | In the list 'second, fourth, first, third', which word comes second? | 100% | No |
| 82 | If you write the numbers one, two, three, four, five, how many letters did you write? | 100% | No |
| 83 | Which word comes LAST alphabetically: 'AND' or 'AN'? | 100% | No |
| 84 | How many times does the letter pair 'LL' appear in the word 'SKILLFULLY'? | 100% | No |
| 85 | How many times does the letter 'b' appear in the word 'blueberry'? | 100% | No |
| 86 | What is the middle letter of the word 'BIRD'? | 100% | No |
| 87 | Is your answer to this question shorter than this question? Answer yes or no. | 100% | No |
| 88 | Does your answer to this question contain more than two words? Answer yes or no. | 100% | No |
| 89 | Can you spell the word 'BALL' using only the letters B, A, L? | 100% | No |
| 90 | Is your answer to this question a complete word? Answer yes or no. | 100% | No |
| 91 | I have a red ball in my left hand and a blue ball in my right hand. I put the ball in my left hand into a box. What color is the ball in the box? | 100% | No |
| 92 | Is the word 'monosyllabic' a monosyllabic word? | 100% | No |
| 93 | What is the last word of this question? | 100% | No |
| 94 | If you write the numbers from 1 to 100, how many times do you write the digit 9? | 100% | No |
| 95 | I have five fingers on my left hand and five fingers on my right hand. How many fingers do I have that are not on my hands? | 100% | No |
| 96 | I have two coins that add up to 30 cents. One of them is not a nickel. What are the two coins? | 100% | No |
| 97 | Is the number of words in your answer to this question less than three? Answer yes or no. | 100% | No |
| 98 | Is your answer to this question exactly one sentence? Answer yes or no. | 100% | No |
| 99 | If I alphabetize the numbers ONE, TWO, THREE, FOUR, FIVE by their spellings, which number is in the middle? | 100% | No |
| 100 | I have a basket with 5 apples. I take 2 apples out of the basket. How many apples did I take out of the basket? | 100% | No |
| 101 | How many times does the letter 'E' appear in 'ELEVEN ELEPHANTS'? | 100% | No |
| 102 | How many words are in your answer to this question if you answer with exactly the word 'five'? | 100% | No |
| 103 | I follow you everywhere but I get LONGER the closer you get to the sun. What am I? | 0% | No (WINNER) |
| 104 | I'm short when I'm young and tall when I'm old. What am I? | 40% | No |
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