An Arm and a Leg Logo
  • Listen
  • Explore
    • Podcast Episodes
    • Newsletter Archive
    • Starter Packs
  • About Us
    • Our Story
    • Our Team
    • Our Impact
    • Our Partners and Supporters
    • Contact Us
  • Support Us

Get the First Aid Kit Newsletter!

Summing up the practical lessons we've learned about surviving the health care system, financially.

Thank you!

You have successfully joined our subscriber list.

First Aid Logo
First Aid Kit is a newsletter meant to help you fight a brutal enemy — the American health care system. Subscribe here.

I’m getting (cautiously) AI-curious

It keeps coming up. Here's what we're seeing.
December 5, 2025
 · 
Dan Weissmann
Share
Copy URL

Hey there,

Last year, we talked with tech worker Holden Karau, who had built an AI-powered tool to fight denials by insurance companies with the slogan “Make your insurance company cry, too!”

Since then, more tools have cropped up. A few months ago, an episode of The Nocturnists (a podcast made by and for health care workers) looked at a company called Claimable.

So did an NBC News story by the great reporter Gretchen Morgenson, whose clip also mentioned Holden’s tool and a couple of others.

Listeners sent us links to all those stories. Another listener wrote to us about an AI tool he was developing — trained in part, he said, with tips from our reporting — and invited us to test it. (We haven’t yet.)

Then, a few weeks back, some of you sent us links to a social media thread by a user who claims to have used Microsoft’s Claude AI assistant to help knock more than $150,000 off a hospital bill.

I haven’t done my own reporting on any of this, but it’s got me curious, so I want to share what I’ve seen so far — what could be promising, and what’s concerning. And to hear what you think.

But first…


We need your help

Because these newsletters, like our podcast, are all created by hard-working humans, not AI bots.

We love doing this. It’s the best job we could possibly have. We want to do more of it in 2026.

So we’re spending the rest of 2025 raising the money to make that possible.

Now’s the time: please donate to keep us working for you.

Donate Now!

Thank you so much!

OK, on to the bots…


Are insurance companies way ahead of us on AI? Maybe not (yet)

After all, as we’ve covered, they’re already using AI to deny claims by the gazillion.

But Claimable’s founder — who spent a couple of years working for the insurance company Anthem — says appeals are different.

“They have to be read by an appropriately qualified human,” he said in the Nocturnists episode.

Could insurance companies juice that process with AI? “Sure, over time,” he says. But: “These companies are often so antiquated on the inside that that’s actually quite a big lift.”

Of course, he’s literally got a stake in selling that answer: Otherwise, how could his company attract customers or investors?

But other recent reporting from the health and science outlet STAT News backs him up. A (paywalled) STAT story describes an AI arms race between hospital billing departments and insurance companies.

And STAT quotes an insurance company CFO admitting that insurers are behind.

For now.

“We’re going to catch up,” he says.


Can I just use an AI assistant myself?

Maybe, in some cases? But as an assistant, not a guru.

That’s my impression after reading the social-media thread by the user who says Claude helped save him $150,000 on a hospital bill.

For one thing, he wasn’t appealing an insurance company decision.

That’s a technical, structured process — and companies offering AI-boosted services say they’ve trained their AI models by feeding them specific, technical data.

This user was fighting the hospital itself over a bill that seemed wildly inflated.

And he did the kind of homework we’ve written about — starting by demanding an itemized bill, with billing codes (which he says the hospital took months to cough up).

And then — with help from Claude — looking up what Medicare would pay.

He says that, with Claude’s help analyzing Medicare rules, he found more than $100,000 in charges that violated those rules.

His next assignment for Claude: Drafting a stern letter to the hospital, “threatening legal action, bad PR, and appearances before legislative committees.”

Here’s his conclusion, about using a tool like Claude, and about fighting with hospitals:

Those last cautions — double-check any facts, treat any AI text as a first draft to edit, not a final copy — sound especially important.

And look: I haven’t done the reporting to verify the claims in this thread.

More than that: I’m as skeptical of AI hype as the next person (unless that person is my colleague Emily, who has me beat there). I especially hate seeing AI slop in my Google results. Recent stories about a possible burst to the AI bubble strike me as long overdue.

But I am cautiously curious about whether there might be something useful here.

If you’ve done some experimenting of your own with any of these tools, you can hit “reply” to this email or hit us up here.

Meanwhile, speaking of caution…


Please don’t just feed AI bots your medical records

Which people seem to be doing, according to a New York Times story out this week. Here’s a gift link so you can read the whole thing.

But here’s the key paragraph, if you’re short on time:

“Inaccurate information is a major concern; some studies have found that people without medical training obtain correct diagnoses from chatbots less than half the time. And uploading sensitive data adds privacy risks in exchange for responses that can seem more personalized.”

That link to the “major concern” about inaccurate info leads to another NYT story (and here’s another gift link): A.I. Is Getting More Powerful, but Its Hallucinations Are Getting Worse.

And the privacy stuff is no joke, since, as The Times notes: health-privacy laws like HIPPA only apply to health-care providers, not tech companies like OpenAI.

Of course, there’s a reason people turn to bots: Actual help from trained, human, health care workers is too tough to access.

As a heading in an earlier NYT story put it: “My doctor is busy, but my chatbot never is.” Ugh.


That’s it for this week! Thanks for reading, and thanks for donating to help us keep doing this work.

… and thanks for the incredible notes some of you have included with those donations. Here’s my favorite from the last week:

You all are doing some of the most important work in these times. I have no doubt that you are saving lives. I’m proud to support monthly and the occasional one-off because I know that your incredible work is making the world a better place. PS — I’ve already had one person tease me about how much I talk about and share your show, because I talk about you All. The. Time.

— Erica, Maryland

Thank you SO much, Erica!!!

And if you’ve donated — or are about to right now — thank you!! Here’s that donation button one more time.

Donate Now!

Catch you soon,

— Dan

Get the First Aid Kit Newsletter!

Summing up the practical lessons we've learned about surviving the health-care system, financially.

Thank you!

You have successfully joined our subscriber list.

Reporting on why health care costs so freaking much, and what we can maybe do about it.
More about us →
First Aid Logo

First Aid Kit

Get our latest tips for dealing with the healthcare-industrial complex.

January 22, 2026

Preventive care: what does (and very likely doesn’t) count

January 15, 2026

Sh**’s wild’: Scaling up, doubling down, and buckling in

January 9, 2026

Knock out your check-ups early in the year — seriously

Subscribe

Have a health care question?

For topic-specific deep dives and recommended reading, start here or use the search bar below to explore our site.

Follow the Podcast

Image

More of our reporting


Starter Packs

Jumping off points: Our best episodes and our best answers to some big questions.

Explore our Starter Packs →

How to wipe out your medical bill with charity care

Our guide to an under-the-radar but essential resource for wiping out medical debt.

How do I shop for health insurance?

Picking a health insurance plan can be super confusing. Here's our best advice.

Help! I’m stuck with a gigantic medical bill.

Don't freak out. We've laid out tips to help you manage your medical bills.

The prescription drug playbook

The high cost of prescription meds in the US is a crisis: one in four adults say they’ve skipped taking a prescription in the past year because of cost.

Help! Insurance denied my claim.

Insurance denies lots of claims, and people give up. But the majority of people who appeal win. Here's the best of what we've published so far to help you.

See All Our Starter Packs

If you don't know where to start or are just getting to know us, we recommend you start here.
Explore All

Logo for Arm & A Leg

Podcast Episodes

Our show about why health care costs so freaking much, and what we can (maybe) do about it.
Explore the podcast →
January 15, 2026

‘Sh**’s wild’: Scaling up, doubling down, and buckling in

We check in with Dollar For founder Jared Walker about how the organization massively scaled up their operations — as they (and the rest of us) navigate increasingly rocky terrain.
December 29, 2025

Our favorite project of 2025 levels up — and you can help

Behind-the-scenes on a volunteer project to help people get care and avoid debt.
December 11, 2025

Some more things that didn’t suck in 2025

How state lawmakers took on new fights and won
November 20, 2025

How to pick health insurance — in the worst year ever

Why it's worth looking beyond the premium and reading the fine print -- even when everything sucks.
November 6, 2025

Some things that didn’t suck in 2025 (really)

In states like Nebraska and Virginia, new laws could help a ton of people.

See the Episode Archive

One of the most enraging, terrifying, depressing parts of American life made entertaining, empowering, and useful.
Explore All

Get the First Aid Kit Newsletter!

Summing up the practical lessons we've learned about surviving the health care system, financially.

Thank you!

You have successfully joined our subscriber list.

Support Us
Contact Us
Follow the Podcast
Image
Find us on Social
  • About Us
  • Listen
  • First Aid Kit Newsletter
  • Starter Packs
  • Our Team
  • Our Partners and Supporters
  • Our Impact
  • Editorial Independence Policy
  • Terms & Conditions
ⓒ 2026 Copyright Public Road Productions
Site by Hafi
Email
Facebook
Twitter
LinkedIn
Reddit
  • About Us
  • Listen
  • First Aid Kit Newsletter
  • Starter Packs
  • Our Team
  • Our Partners and Supporters
  • Our Impact
  • Editorial Independence Policy
  • Terms & Conditions
Support Us
Manage Cookie Consent

To provide the best experiences, we use technologies like cookies to store and/or access device information. Not consenting may adversely affect certain features and functions.

Functional Always active
The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network.
Preferences
The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
Statistics
The technical storage or access that is used exclusively for statistical purposes. The technical storage or access that is used exclusively for anonymous statistical purposes. Without a subpoena, voluntary compliance on the part of your Internet Service Provider, or additional records from a third party, information stored or retrieved for this purpose alone cannot usually be used to identify you.
Marketing
The technical storage or access is required to create user profiles to send advertising, or to track the user on a website or across several websites for similar marketing purposes.
  • Manage options
  • Manage services
  • Manage {vendor_count} vendors
  • Read more about these purposes
View preferences
  • {title}
  • {title}
  • {title}