The HSA strategy everyone recommends — pay out of pocket, invest the account, reimburse yourself years later — fails quietly at one point: proof. Here's what each alternative actually gets you.
✗Receipts prove a bill existed — not that you paid it out of pocket, weren't reimbursed by insurance, didn't deduct it on Schedule A, and hadn't already withdrawn against it. Those are the four questions an examiner asks, and a shoebox answers none of them. It also fails your executor: at the account holder's death, a non-spouse beneficiary has one year to apply your expenses against the taxable balance — nobody reconstructs a decade of paper in a year of grief.
✗Better than nothing, but it's testimony, not evidence: no source documents attached, no payment linkage, no provenance, editable after the fact (which is precisely what an auditor assumes). And you're the matching engine — every EOB against every statement, by hand, forever.
✗It stores files; it doesn't know what your insurer adjudicated or what your card paid — the two halves of substantiation. It's also theirs: change custodians and the history doesn't follow. This ledger is custodian-neutral and everything exports byte-identical, forever, free.
✓The good ones do FIFO reimbursements, growth projections, and Form 8889 helpers — so we do all of that too. What none of them do: match EOBs to bank payments automatically (including in-progress payment plans), keep three levels of proof with per-year 1099-SA gap detection, attribute every expense to a household member with the death rules enforced, chain the history with tamper-evident hashes, read scans with free local OCR, or hand your advisor a consent-based portal. Feature lists are copyable; a five-year evidence chain anchored in time is not.
✓Documentation is the difference between taxed and untaxed money: a family documenting $3,000/yr for 20 years protects about $27,000 of tax; a retired couple's Medicare premiums are a ~$40,000 pipeline; three years of in-home care, ~$74,000 kept. Run your own numbers on the What it's worth page.
Free plan includes every export, forever. Not tax advice.