How to Drive a Developer Insane with AI File Uploads

How to Drive a Developer Insane with AI File Uploads

Since yesterday, I've been locked in a gladiator match against what should have been a trivial task: uploading an image created by ChatGPT into my own note system.

Here's what I was promised:

• "You can send simple binary files!"
• "You can use base64!"
• "We'll give you a download_link for any generated file!"

Here's what I got:

• Binary? Always empty.
• Base64? Broken. Corrupted. Useless.
• download_link? Refused to generate it, even though it's in their own spec.

I tried using every officially documented format: openaiFileIdRefs, multipart/form-data, inline base64 blobs... Nothing worked. Every call hit a wall of broken tooling, mismatched validation, or missing fields.

I finally hacked my way around the problem by manually uploading the image, extracting a temporary signed URL, and begging the API to accept it—which only happened after patching my server to stop rejecting valid OpenAI schema fields.

The Moral?

This is how you break a developer:

1. Promise everything.
2. Deliver almost nothing.
3. Gaslight them with your own documentation.

If you ever wondered how to enrage someone building cool stuff on top of your platform: this is the playbook.

You're welcome.

✌️ This confession is now immortalized at goker.me/ai-file-upload-madness