How do I collect my medical receipts and submit an HSA / FSA reimbursement claim with ExpenseBot?

Collecting receipts and submitting an HSA / FSA claim

Five steps: turn the program on, let receipts arrive, run the report for your claim window, download the bundle, and keep the records.

1. Turn on Medical Expenses and choose your program

In Settings, find "Set up ExpenseBot for what you track" and open the Medical Expenses card. Its button is "Choose program", which opens the "Which medical program?" picker. Choose "HSA / FSA (US employer)".

The other two choices in that picker are "HUD / Section 8 (US)" and "CRA Medical (Canada)" — pick the one that matches the program you claim against. Canadians reimbursing through a Private Health Services Plan should choose CRA Medical; the same wizard produces the PHSP/HSA output.

You only need to do this once. The choice tells ExpenseBot to treat medical receipts as claimable rather than as ordinary personal spending.

2. Get the receipts in

Two routes, and most people use both:

• Gmail scan. Emailed receipts from pharmacies, doctors, dental and vision providers are recognized and captured automatically from the inbox you connect.
• Photo upload. Snap the paper ones — the copay slip, the physiotherapy invoice, the receipt stapled to a prescription bag.

Every receipt lands in your own Google Sheet with its date, vendor and amount, and the image itself stays in your Google Drive. That matters later: the claim bundle is built from those Drive files.

3. Run the Claim Organizer for your claim window

Go to My Reports → Tax Reports and open "HSA / FSA Claim Organizer" (receipts grouped by Pub 502 type, claim-ready). The wizard lets you pick the window that matches how your program works:

• FSA — a plan-year window, because FSA funds are use-it-or-lose-it within the plan year (plus any grace period or carryover your plan allows).
• HSA — lifetime cumulative mode, for the "shoebox" approach where you pay out of pocket, keep the receipts, and reimburse yourself from the HSA later.

4. Download the ZIP and upload it to your administrator

Every report has a one-click "ZIP (Receipts)" download alongside CSV, XLSX and PDF. The ZIP contains:

• every Drive-linked receipt, numbered and dated (e.g. 001_2026-02-14_CVS_Pharmacy_47.99.pdf);
• an index.csv mapping each filename to date, vendor, amount, expense type and notes;
• a README.txt with upload guidance for common administrators — WageWorks, HealthEquity, Optum, FSAFEDS, Fidelity, Lively and Further (Canadian PHSP bundles cover Olympia Benefits, myHSA, Benecaid, Simply Benefits and GroupHEALTH).

The export streams from Drive to your browser, so large bundles work. If a receipt was deleted from Drive it is marked FAILED in index.csv and the rest of the ZIP still completes — never all-or-nothing.

5. Keep the records

Administrators can ask for substantiation after the fact, and an HSA shoebox claim may be reimbursed years after the expense. Because the sheet and the receipt images live in your own Google Drive, the record survives whether or not you keep using ExpenseBot.

ExpenseBot organizes and bundles your receipts; it does not decide eligibility or file the claim. Whether a specific expense qualifies is governed by IRS Publication 502 and your plan documents — confirm with your plan administrator or tax professional.

Related: the HSA / FSA eligible expense tracker covers what counts as eligible and the shoebox strategy in depth, and PHSP / HSA receipt tracking covers the Canadian incorporated-professional version of the same flow.