Check which expenses your HSA or FSA can pay for (and use it before you lose it)
Have AI sort your health spending into likely HSA (health savings account)/FSA-eligible and not-eligible lists, using IRS Publication 502 and your plan's rules.
1. Copy this prompt
Paste it into ChatGPT, Claude, Gemini or Grok (the free versions work), then replace the [highlighted brackets] with your details. Leave out account numbers and SSNs.
I have a [HSA / health FSA / limited-purpose FSA] with $[BALANCE] left and a deadline of [DATE]. Here are expenses I've had or plan to have: [LIST]. Using IRS Publication 502 as the main source, 1) sort them into likely eligible, possibly eligible with a letter of medical necessity, and not eligible, 2) suggest eligible purchases I'm likely to need anyway, and 3) list what to confirm with my plan administrator. Say clearly when you're unsure.
2. Follow these steps
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What to expect, and what to do if they say no
What happened when people tried it
- We haven't verified a real-world example for this one yet, so it's a tool guide plus a prompt. Tried it? Tell us what happened (link below).
Why this works
The problem: People leave FSA money unused at year-end or pay out of pocket for things their HSA could cover tax-free.
How AI helps: AI can check items against IRS rules, flag which need a doctor's letter, and remind you about your plan's deadlines and grace periods.
Tools & what they cost
| Tool | Cost |
|---|---|
| ChatGPT | Free option available (Paid upgrades exist, but the free version works for this) Free tier; paid plans available |
| Claude | Free option available (Paid upgrades exist, but the free version works for this) Free tier; paid plans available |
| IRS Publication 502 | Free (No cost at all) Free |
| IRS Publication 969 (HSAs and FSAs) | Free (No cost at all) Free |
What do these labels mean?
- Free No cost at all.
- Free option available Paid upgrades exist, but the free version works for this.
- Costs money You pay a set price or subscription.
- Takes a cut of savings Charges a percentage of what it saves you.
- Time · Difficulty Our estimates for a typical first try, not guarantees.
- Reported What the linked source says happened, often self-reported. Your results will vary.
Watch out for
- No verified AI-specific success story yet. This is a how-to guide built on official sources.
- Your plan administrator has the final say; some plans are narrower than the IRS rules.
- HSA money spent on non-qualified expenses can be taxed and penalized.
Was this helpful?
Tried it? Tell us what happened, good or bad. We read every reply and may share success stories (only with your OK).
Sources
Last verified 2026-10-19. Not financial, legal, tax or medical advice. Disclaimer.