A note from the founder
I built this because of my son Roi.
When my wife and I were expecting Roi, I did what most first-time parents do: I bought everything. Bottles, a thermometer, a breast pump, sunscreen, more diaper cream than any one baby needs. All of it out of pocket.
A few weeks in, I was looking at our spending and feeling a real hole in our budget. That's when I remembered I'd contributed $500 to an FSA at the start of the year, almost as an afterthought, a rainy-day thing.
So I started checking. The breast pump? Eligible. The thermometer? Eligible. Sunscreen above SPF 15? Eligible. Half of what I'd been quietly absorbing into our credit card bill could have come out of an account I'd already funded with pre-tax dollars.
I'd been losing money to my own ignorance. I'm guessing I'm not alone in that.
02 / Why generic AI fails
I tried asking ChatGPT. Then Claude. Then ChatGPT again.
The first thing I did, naturally, was ask an AI. I pasted in items from my receipts and asked if they were HSA/FSA eligible.
The answers were close enough to sound right and just wrong enough to be useless. ChatGPT would say one thing on Monday and contradict itself on Tuesday. Claude hedged on items the IRS is unambiguous about. Neither would cite a source I could take to a reimbursement form.
That's not a bug. It's the design. These models are trained on the open web: forum posts, outdated blog articles, marketing pages from FSA stores trying to sell you things. The IRS publications might be in there too, but they're a drop in an ocean of louder, less accurate sources. And the model won't tell you which one it pulled from.
So when you ask “is melatonin eligible?”, you're not getting the IRS's answer. You're getting an average of everything the internet has ever said about melatonin. For something tied to your tax-advantaged dollars, that's not good enough.
“Melatonin may be eligible in some plans — though policies vary. You may want to check with your plan administrator for confirmation.”
Eligible as an over-the-counter medicine. CARES Act 2020 §3702 removed the prescription requirement.
IRS Pub. 502 (2025) · CARES Act §3702
03 / What I built
So I built the tool I wanted.
EligibleCheck does one thing: it tells you whether something is HSA or FSA eligible, and it shows you the rule it's working from.
You can paste a product name, upload a photo of a receipt, or drop in a URL from Amazon or your pharmacy. You get back a clear verdict: eligible, not eligible, or eligible with a letter of medical necessity. Plus the language you'd actually put on a reimbursement form.
The verdicts are grounded in the documents that actually matter:
Not the open web. Not a 2019 blog post. The source material your plan administrator is using when they approve or deny your claim.
04 / The math nobody runs
The math nobody runs
Here's what nobody tells you. An HSA or FSA saves you 24% to 32% on every eligible dollar, once you add up federal, state, and FICA at a typical bracket. And if you pay with a credit card and submit for reimbursement instead of swiping the FSA debit card, you keep the 2% to 5% cashback from that card on top. Tax savings and cashback. Stacked.
Think about a family spending a few thousand dollars a year on the kind of stuff that quietly qualifies: pain relievers, sunscreen, allergy meds, period products, baby care, contact lenses, therapy copays. That's hundreds of dollars left on the table. Every year. By people who already funded the account.
I built EligibleCheck because that gap shouldn't exist. The money is already yours. The rules are already public. The only thing missing was a tool that connects the two in under ten seconds.
The money is already yours.
The rules are already public.
Run your own numbers
Try it on something you bought last week.
The fastest way to see if EligibleCheck is worth your time is to test it on a receipt that's already sitting in your inbox. Most people find something eligible on the first try.