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# The Screwtape Challenge: What an AI Revealed
- URL: https://www.thehiddenorchard.com/the-screwtape-challenge-what-an-ai-revealed/
- Published: 2026-10-30T16:35:00.000Z
- Updated: 2026-10-30T16:34:59.000Z
- Description: Your favorite AI knows your habits. In this challenge, ask it how an adversdary would use them against you.
- Author: James - The Hidden Orchard
- Tags: Mussar, Supernatural

C.S. Lewis’s masterpiece, [*The Screwtape Letters*](https://link.amazon/B0jbgZtGU?ref=thehiddenorchard.com), is written from the perspective of Screwtape, a senior demon training his nephew Wormwood. 

Wormwood is a junior demon learning how to subvert the spiritual development of a human being. Screwtape's counsel is subtle, and it serves as a striking commentary on the human psyche.

A friend shared with me a brilliant idea where someone used their favorite AI LLM to write a similar letter about themself.

## The Challenge

### Step 1

In your favorite AI agent/LLM, use the following prompt:

> Write a Screwtape letter about me based on what you know of me from our conversations, in the format of CS Lewis's book.

The results may vary, but a picture will emerge.

### Step 2

Then ask the LLM:

> Reverse-engineer this letter. What are the key steps I should take to grow?

Feel free to share your thoughts and feedback in the comments below.

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