Questions people actually ask

Yes. There is no deadline for reimbursing a qualified expense, as long as it was incurred after the HSA was established, you have the records, and it wasn't deducted or otherwise reimbursed. The IRS's own guidance contemplates exactly this — the whole strategy rests on keeping proof, which is what this ledger is.

That the expense was qualified (the EOB or receipt), that you paid it and weren't reimbursed by insurance (the bank record against the adjudication), and that no double benefit was taken (no Schedule A deduction; distributions on your 1099-SA traced to documented expenses). That's precisely the three-level structure of the audit packet.

You press Export → Audit packet. It groups exhibits by tax year, pairs every expense with its payment, states the statutory basis, includes your per-year return status and 1099-SA reconciliation, and carries SHA-256 fingerprints plus a tamper-evident event chain. The response to a letter is a print button.

Yes — qualified expenses of your spouse and dependents count even if they're on entirely different insurance. Every entry here is attributed to a named household member, which is both the legal basis and how the packet presents it.

Expenses incurred before a family member's death remain fully reimbursable; the ledger refuses anything dated after (it can't qualify). If the account holder dies, a spouse beneficiary takes the HSA as their own; any other beneficiary owes tax on the balance minus your qualified expenses paid within one year — a deadline only an organized, per-person ledger can meet.

Once the account holder is 65: Parts A, B, C, and D and employer retiree coverage, yes — Part B alone is $202.90/month in 2026 (the standard premium; income-related surcharges run higher), usually withheld from Social Security, with the SSA-1099 as proof (the premium tracker handles the whole series). Medigap never qualifies at any age, and the app refuses it so an audit can't.

Yes — medical travel at the IRS standard rate (20.5¢/mile for January to June 2026, 23.5¢/mile from July 1, 2026) plus parking and tolls. Log the trip with its destination and the ledger applies the correct rate for the date; the log itself is the substantiation.

Per IRS Rev. Proc. 2025-19: $4,400 for self-only coverage and $8,750 for family coverage, plus a $1,000 catch-up if you're 55 or older. To contribute at all you need a qualifying high-deductible plan: a deductible of at least $1,700 (self-only) or $3,400 (family), with out-of-pocket maximums no higher than $8,500 and $17,000. Contributions are the one part of the strategy with a deadline; reimbursements have none.

Uploaded EOBs, receipts, and statements are encrypted with AES-256-GCM before they are written anywhere, fingerprinted with SHA-256, and stored either on the server's persistent disk or in a private object-storage bucket; either way the storage only ever holds ciphertext, and the key never leaves the application. Account records, matches, and decisions live in a database on the same persistent disk. Nothing is stored in your browser except a session cookie.

Yes. Image-only PDFs and photos are read by built-in OCR at no cost; genuinely rough scans fall back to AI extraction (if configured) or quick manual entry — and the original always attaches as evidence regardless.

Record it in the per-year status. If you claimed medical expenses on Schedule A, mark those specific expenses as deducted — they're excluded from the reimbursable balance and listed transparently in the packet (specific identification; the exclusion follows the year you paid, matching Schedule A).

Documents are encrypted at rest (AES-256-GCM), fingerprinted at upload, and served only to you; passwords are hashed with scrypt; sessions, headers, and cross-origin protections follow current practice; and if you link an advisor they see summary numbers and status only — never your documents — revocable in one click.

The opposite, on purpose. Export everything (.zip) works on every plan including free: every original file byte-identical, all data with raw payer payloads, the packet, and a fingerprint manifest. A record system you can't leave is one you can't trust.

While HSAMatch is in preview, everything is free — matching, connections, and every export. Paid tiers will arrive later; exports will stay free on every plan, permanently.

All of them — the ledger is custodian-neutral because it works from your insurer's adjudications and your bank records, not the custodian's app. Record your balances (or link via bank connection) and the hero shows exactly how much you can withdraw tax-free today.

No — it's record-keeping and substantiation software. The math, statutes, and packet language are built to professional standards, but your CPA or advisor owns the conclusions. (Many advisors use the built-in portal for exactly that.)

More than most people think. OTC medicines and menstrual products have qualified without a prescription since 2020; sunscreen (SPF 15+), first-aid supplies, breast pumps, and mileage to appointments all count. The category people miss: dual-use items — ordinarily personal, but qualified with a Letter of Medical Necessity (LMN) from a provider naming the condition they treat. Attach the LMN to the expense and it belongs in the packet. This is the same reference built into the app's eligibility search, grounded in IRS Pub. 502.

Automatically eligible (53)

Eligible with a Letter of Medical Necessity (7)

Never eligible (13)

Reference, not tax advice; edge cases live in Pub. 502.