Reimbursing yourself with Smart Reimbursement
Smart Reimbursement is the guided workflow that turns your tracked expenses into actual money out of your HSA.
How it works
- From the Dashboard, click Smart Reimbursement.
- We show you the total amount available to reimburse — the sum of all your eligible, out-of-pocket expenses with receipts that haven't been claimed yet.
- Choose:
- Reimburse it all — claim every available expense.
- Set a target amount — say "I want to pull $5,000" and we pick which expenses to claim, oldest first, until we hit your number.
- Review the list of expenses we picked.
- Confirm. We mark each expense as Reimbursed in your ledger.
Why "oldest first"
There's no IRS rule saying you have to reimburse in any particular order, but oldest-first is generally the cleanest record-keeping pattern — it's the easiest to explain ("I paid this in 2019, I reimbursed myself in 2026") and matches the typical year-by-year structure of Form 8889.
What the app does and doesn't do
Smart Reimbursement does:
- Mark expenses in your ledger as reimbursed
- Update your Dashboard totals
- Save the reimbursement event for your records
Smart Reimbursement does not:
- Move money. We can't pull money out of your HSA — that's between you and your HSA provider.
After you confirm in Reimbursable, log into your HSA provider's website (Fidelity, HSA Bank, etc.) and request a distribution to your linked checking account for the amount we showed. That's the actual money movement.
Required: receipts and payment source
We won't include an expense in Smart Reimbursement unless:
- It has a receipt attached, AND
- It has a payment source set (so we know if it was paid out-of-pocket vs. with the HSA card already)
If you have eligible expenses missing one of these, you'll see a warning at the top of the Smart Reimbursement page with a link to fix them.
Undoing a reimbursement
Go to the Expenses page, open any reimbursed expense, and click Mark as not reimbursed on the detail page. The expense becomes available again for future reimbursement.
Updated on: 05/06/2026
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