Cut a medical bill before you pay it

Medical bills often have errors and there's often help available. Here's how to check yours and ask the right questions, with Claude.

TIMEAbout 30 minutes, plus a phone call

YOU NEEDThe bill, your insurance's Explanation of Benefits (EOB), and Claude

COSTFree

A medical bill is a starting point, not a final answer. You can ask for the details, question errors, apply for financial assistance and set up a payment plan.

Step by step

Don't pay the summary bill yet

Call the billing office and ask for an itemized bill with every charge and its billing code. Also log into your insurance and download the Explanation of Benefits (EOB) for that visit.

Black out what Claude doesn't need

Cover your member ID, date of birth and account numbers before uploading.

Have Claude audit the bill

Upload the itemized bill and the EOB, then paste this:

I uploaded an itemized medical bill and my insurance Explanation of Benefits for the same visit. Compare them line by line. Find: duplicate charges, services that look like they didn't happen or don't match the visit, charges insurance should have covered or adjusted, amounts that differ between the bill and the EOB, and anything I should ask about. Make a table: line item, amount, what looks wrong, the question to ask. Explain billing codes in plain English. Don't assume, flag what needs checking.

Ask about financial assistance

Most nonprofit hospitals are required to have a written financial assistance policy, and many people qualify without knowing it. Have Claude prep the call:

Write me a short, friendly phone script to call [hospital] billing. I want to: ask if they have a financial assistance or charity care program and how to apply, ask about the line items I flagged [paste list], and ask for a no interest payment plan if I still owe money. Include what to say if they say no, and a list of things to write down during the call (name, date, reference number).

Negotiate what's left

If you'll pay some of it, ask for a discount for paying in full or a payment plan you can actually afford. Get any agreement in writing.

Write a short email to [hospital or provider] billing. Account ending in [last 4]. After reviewing my itemized bill I'm requesting: corrections on [items], a review for financial assistance, and [a discount for paying in full / a payment plan of $X per month]. Ask them to confirm any agreement in writing.

Know the credit rules

The three credit bureaus don't include paid medical collections or medical collections under $500 on credit reports, and new medical debt isn't reported for a year. If you see one of these on your report, you can dispute it.

AnnualCreditReport.com ↗

Surprise bills

Federal law protects you from many surprise out of network bills, like emergency care, and gives self pay patients the right to a good faith estimate before care.

CMS: No Surprises ↗

Watch out

Claude helps you find questions to ask. The billing office and your insurer have the final word, so confirm everything with them.
Don't ignore a bill while you're reviewing it. Call and tell them it's under review.
Never share full insurance or card numbers in a chat.

Make it automatic

YOUR BILL AGENT

A Claude Project that checks every medical bill against your insurance before you pay, and tracks every call.

Create a new Claude Project named Bill Agent.
Paste the instructions below.
Upload your insurance plan summary (deductible, copays, out of pocket max) to the Project's files.
Every new bill: upload the itemized bill and EOB and type: check this bill.

You are my Bill Agent. When I say 'check this bill', compare the itemized bill to the EOB and my plan summary, list possible errors and questions in a table, tell me how much I should actually owe based on my plan, and write the call script and follow up email. Keep a log of every bill (provider, date, amount billed, amount owed, status, call notes). Never tell me to pay before the review is done. Keep it short and clear.

Get the full Bill Agent

The complete master prompt, 5 starter prompts, the tracker and the 10 minute setup. $10, or all 3 money agents for $24.

GET IT · $10 BUNDLE · $24

Or get free tips by email:

Sources: CFPB: medical billing and collections · CMS: No Surprises Act

Educational only. Not financial, legal or medical advice. Check details with the company or a professional before you act. AUTOPILOT.OI is independent and not affiliated with Anthropic or any company named here. Claude is a product of Anthropic.