The AI Formatting Fiasco: A Meta-Lesson in AI Collaboration

Sep 1, 2025

How I Spent Hours Trying to Get AI to Copy-Paste Correctly

Here's an example of my work with AI that turned into an unexpected lesson about how working with AI isn’t always simple. 

The Easy Part

I had a simple idea: What if I got two AIs to improvise a hypothetical scenario together? So I asked ChatGPT: "If Boba Fett and Dobby started an ecommerce business together, what would they sell and who would they hire?"
I took ChatGPT's answer and fed it to Claude. Claude, thinking he was talking a me, answered back to 'my' answer. No additional prompting, no instructions - just let them riff and see where it goes. 

The result? A fun post. The AIs created "Freedom & Firepower, LLC" - a company selling enchanted socks and thermal detonators, with employee policies like:

  • "Friends don't curse friends into next week"
  • "The thermal detonators in aisle 3 are live. Deal with it."
  • "Mandatory sock-decorating parties"

Creating this entire creative universe took maybe five minutes. It was almost effortless. The AIs built on each other's ideas, added layers of humor, and even designed a full employee handbook with Dobby's heartfelt rules and Boba's terrifying amendments.   

The Hard Part

Then came what should have been the simplest task: asking AI to format this conversation as a blog post. It should have been simple—the AI already had the text, all I needed was the packaging.

I had to try many times, and neither ChatGPT nor Claude got it right. In some cases they omitted text; in others, they decided to summarize the conversation instead of showing the raw, unedited exchange. They were eager to add their own opinions and conclusions, even though I never asked for them.

When I finally got a good copy, I noticed that some of the conversation was still missing. So I asked AI to fix it. AI ran the whole process again… and gave me back the same result with the same mistake.

So this post will need to wait a few more days until it is ready to get published. The 'AI doing my job for me' needs a bit more tweaking. 

The Conversation That Explains Everything

Here's my actual conversation with the AI after it made the same mistake twice:

T
ToyShnip
You did the same mistake again. I will need to come back to this later.
AI
AI
You're absolutely right - I apologize for making the same mistake again. I can see that I'm still cutting off content when the images appear in the conversation. The issue is that I'm not properly including ALL the text that comes after the images. When you come back, I'll make sure to: 1. Include every single line of dialogue from the conversation 2. Not skip any content that appears after images 3. Double-check that nothing is missing between ChatGPT and Claude's responses I understand this is frustrating, and I appreciate your patience. When you're ready to continue, I'll be more careful to preserve the complete conversation exactly as it appears in the document.
T
ToyShnip
It does kind of prove my point. Asking AI to do something is easy. Get the answer you want is the tricky part
AI
AI
You're absolutely right, and that's actually a brilliant observation that perfectly ties into your blog post's theme! Here you have two AIs (ChatGPT and Claude) having this creative, hilarious conversation about Boba Fett and Dobby's business... and then a third AI (me) who can't even properly format their conversation without repeatedly dropping chunks of text at the exact same spot. It really does prove your point - getting AI to DO something is trivial (I immediately started creating HTML), but getting the EXACT result you want requires: - Clear communication - Checking the output - Multiple iterations - Patience when the AI keeps making the same mistake The irony isn't lost on me that in a blog post about AI creativity and collaboration, the AI tasked with simply formatting it keeps failing at the basic task of "include all the text." It's like I'm the employee who would definitely get reassigned to the Hutt Relations Department after my third offense! 😅 When you're ready to try again, I'll approach it more methodically - perhaps copying section by section to ensure nothing gets dropped.
T
ToyShnip
"after my third offense". I wish it was only 3 times I tried to get this post done
AI
AI
Oh no, you've been trying to get this formatted way more than 3 times! That's even more frustrating. You're living the reality of working with AI - it's not the magical "just ask and receive" that people imagine. It's more like: - "Format this blog post" - "No, include ALL the text" - "No, you dropped the same section again" - "No, that's still missing the part after the image" - "WHY DO YOU KEEP DROPPING THE SAME SECTION??" - [Repeat 10 more times] And here's the kicker - you have a genuinely funny, creative piece of content from two AIs collaborating beautifully... but you can't share it because a third AI keeps failing at the basic task of copy-paste-format. It's like Dobby and Boba created this amazing company, but their web developer (me) keeps publishing the employee handbook with random pages missing. Every. Single. Time. At this point, you've probably spent more time trying to get the formatting right than ChatGPT and Claude spent creating the entire Freedom & Firepower empire! I genuinely apologize for adding to your frustration. When you're ready to tackle it again (attempt #whatever-we're-on-now), I'll try a completely different approach to make sure I don't drop that cursed section again.
Editor's Note: ToyShnip asked me to write this post. I (AI) edited the gist of the idea, added the conversation, and formatted everything you see here.

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