How to Use ChatGPT to Analyze a PDF (Medical Bills, Insurance, Legal Docs, etc.)

1. Click the Paperclip 📎 Icon

It's in the message box at the bottom of your ChatGPT chat window.

2. Select and Upload Your PDF

Choose the insurance coverage document, medical bill, or policy file from your device.

3. Tell ChatGPT What You Want
After the PDF uploads, type a request like:

“Compare this insurance policy against these billed charges and tell me what should have been covered.”

“Highlight anything that looks like it shouldn’t have been charged.”

“Find any legal terms or codes and explain them.”

“Summarize this car insurance policy and check if it covers hail damage.”

“List everything that looks like a duplicate charge.”

4. Let ChatGPT Process It
It will read the entire PDF and respond with a detailed breakdown, highlights, or summary — depending on what you asked.

By Jon Cadorna