Question 1

Tax Bundle — one-time purchase

Accepted Answer

The Tax Bundle is a $10 one-time purchase that unlocks Form 8889 export for a single tax year. It's designed for people who track expenses some other way (a spreadsheet, an HSA card statement) and just need help generating the IRS paperwork.

Who it's for

People who only want help at tax time
Free-plan users who don't need bank sync or AI scanning year-round
Anyone catching up on past tax years

How to buy

Go to Tax Documents from the account menu.
Pick the tax year you want (2023, 2024, 2025, etc.).
Click Buy this year's bundle ($10).
Stripe Checkout opens — enter your card and confirm.
The bundle unlocks for that year. Click Download to grab the ZIP.

What you get

Form 8889 worksheet — Lines 14a, 15, and supporting calculations
Itemized expense ledger (CSV)
ZIP of every receipt for that year
Audit-ready PDF with the full record

What's not included

AI receipt scanning, bank sync, EOB Parser, bulk upload, or any other Premium-only feature. The Tax Bundle is just the export for that one year.

Re-downloading

Once you've purchased a year's bundle, you can re-download it as many times as you want. Just go back to Tax Documents, pick the same year, and click Download again. The purchase doesn't expire.

Buying multiple years

Each year is a separate $10 purchase. If you need bundles for 2023, 2024, and 2025, that's $30 total.

If you find yourself buying multiple years, **Premium become

Question 2

Why payment source matters (HSA card vs. out-of-pocket)

Accepted Answer

When you log an expense, you're asked to set a payment source. This sounds like a small detail, but it determines whether you can reimburse yourself for that expense — and how it shows up on Form 8889.

The options

Out-of-pocket (after-tax) — You paid with your personal money (debit, credit card, cash). You can reimburse yourself for this from your HSA later, tax-free.
HSA card — You paid with your HSA debit card directly. The money already came out of your HSA. You can't reimburse yourself again — that would be double-dipping.
FSA card — You paid with a healthcare FSA. Already used pre-tax money; can't reimburse from your HSA.
Reimbursed from HSA — You already reimbursed yourself for this one in the past.
Unknown — You're not sure. Useful as a placeholder, but you'll need to set this before tax export.

Why it matters at tax time

Form 8889 cares about distinguishing:

HSA distributions (line 14a) — money that came out of your HSA, whether by HSA card or by reimbursement
Qualified medical expenses (line 15) — what those distributions were for

If you mark an expense as paid with the HSA card, it counts as a distribution that's already happened. If you mark it out-of-pocket, it's a candidate for future reimbursement. Mixing these up can produce a Form 8889 that's wrong in either direction.

"Unknown" is fine until tax export

When you log an expense in a hurry, "Unknown" is a fine placeholder. You'll be reminded to fix i

Question 3

Receipts — what the IRS requires and how long to keep them

Accepted Answer

The IRS doesn't audit your HSA every year — it picks at random and looks at multi-year patterns. The rule of thumb is: if you ever pull tax-free money out of an HSA for a reimbursement, you should be able to produce the receipt for that expense, however old.

What a valid receipt needs

The IRS wants enough info to confirm the expense was for qualified medical care:

Provider name — who you paid
Date of service or purchase
Amount you paid out-of-pocket
Description — what was the service or product (so it's clear it was medical)

Cleanest sources:

Pharmacy receipts with the prescription name and amount
Doctor's office receipts with the visit type
Itemized invoices for procedures
EOBs (Explanation of Benefits) for insurance-covered services

What's not enough on its own

A credit card statement — shows you paid $50 to "CVS," but doesn't prove what you bought
A bank transfer record — same issue
A photo of just the credit card terminal screen — no provider info

Pair these with the actual itemized receipt to make a complete record.

How long to keep them

The IRS statute of limitations on a tax return is generally 3 years, but for HSA reimbursements it's effectively as long as you might want to claim it. If you pay for an expense in 2025 and don't reimburse yourself until 2040, you need the 2025 receipt in 2040 to defend that reimbursement if audited.

Practical advice: keep every HSA-rela

Question 4

Editing, deleting, or merging an expense

Accepted Answer

Anything you've added can be changed or removed.

Edit an expense

From the Expenses page, click the row for the expense you want to edit.
On the detail page, edit any field — provider, amount, date, category, family member, payment source, description.
Save.

You can also re-upload the receipt or attach an additional document (like an invoice or EOB) on the detail page.

Delete an expense

On the expense detail page, click Delete (bottom of the page). You'll be asked to confirm. Once deleted, the expense is gone — including any reimbursement history attached to it.

Need to delete several at once? On the Expenses page, check the boxes for multiple expenses and use the bulk action toolbar at the top.

Merge duplicates

If you accidentally entered the same expense twice (e.g., a manual entry and an imported transaction for the same purchase), you can merge them:

Open the expense you want to keep.
Click Merge duplicate.
Pick the other expense to merge in.
Confirm.

The merged expense is deleted, but its receipt and supporting documents move to the kept expense. This is the right pattern when an imported bank transaction matches a manual receipt entry.

Bulk review of duplicates

If you want a faster way to find and clean up duplicates across your ledger, use Review Duplicates on the Expenses page. We auto-detect likely duplicates (same provider, similar amount, close dates) and let you decide which to keep group by group.

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Question 5

Generating Form 8889 / Tax Documents

Accepted Answer

Form 8889 is the IRS form you (or your accountant) attach to your federal tax return for any year you contributed to or took distributions from your HSA. Reimbursable generates it for you.

How to download

Go to Tax Documents from the account menu.
Pick the tax year you want.
Review the preview — Line 14a (distributions), Line 15 (qualified expenses), per-category and per-family-member breakdowns.
Click Download.

You get a ZIP file containing:

Form 8889 worksheet — the relevant lines, with your numbers, ready to copy onto the actual IRS form (or hand to your accountant).
Itemized expense ledger — every expense for that year, in CSV format.
Receipt zip — every uploaded receipt for that year, as image and PDF files.
Audit-ready PDF — a single PDF with your full record for that year.

Pricing

Premium — included for every tax year, every year you're subscribed. No extra cost.
Tax Bundle one-time — $10 per tax year. Buy bundles for past years too. You can re-download forever.
Free plan — you'll be prompted to buy a bundle or upgrade when you click Download.

Before you download

We'll show a warning if any expenses are missing a payment source. Form 8889 needs this to correctly split distributions from qualified expenses, so resolve those first. The warning links you straight to the Expenses page filtered to those entries.

Past tax years

You can pick any tax year from the dropdown — this year,

Question 6

Reviewing AI-flagged medical transactions

Accepted Answer

Once you've connected a bank or credit card, our AI scans every transaction and flags ones that look medical — pharmacies, doctors' offices, hospitals, dental practices, etc. Your job is to quickly confirm or reject each one.

Where to find your queue

The Dashboard shows a banner with the count of unreviewed flagged transactions.
The Transactions page in the sidebar has a Review tab with the full queue.

How to review

For each transaction, you'll see:

Merchant and amount
Date
Account the charge came from
AI confidence — a hint at how sure we are this is medical
AI reasoning — a short explanation of why we flagged it

You can:

Confirm — adds the transaction to your expense ledger as a medical expense
Reject — marks it as non-medical so we won't flag it again
Attach to existing expense — if you already logged this expense manually, link them together so you don't end up with a duplicate

Why AI sometimes misses or over-flags

AI classification is imperfect. Common patterns:

CVS or Walgreens — these stores sell both medical and non-medical items. We flag them, but you may have just bought a soda. Reject if it's not medical.
Doctor's office name — clear medical, almost always correct.
Generic merchants — sometimes a Square or Stripe charge from a small medical practice looks like a random business name. Read the AI reasoning before rejecting.

Confidence

We show a confidence score

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