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FoundationsNovember 29, 2025

The Modern FSA Playbook: Make Tax-Free Dollars Feel Automatic

A calm, modern explanation of Flexible Spending Accounts for people who do not have time to babysit paperwork.

8 min readFSA 101 • Guides • Tax savings
Key takeaways
  • FSAs are funded with pre-tax dollars, which means you keep roughly 30% more spending power when you use the account.
  • Eligibility is broader than people assume—OTC meds, therapy devices, first aid, and even sunscreen often qualify.
  • Administrators reimburse faster when every line item maps to a receipt, provider, amount, and medical purpose.
  • A lightweight quarterly ritual plus automation keeps you from scrambling in December.
Baseline

FSAs in 60 seconds

A Flexible Spending Account is an employer-sponsored benefit where contributions are deducted from your paycheck before taxes and earmarked for eligible health expenses.

You decide during open enrollment how much of your salary to route into the account (up to the IRS limit). That full election is often available on day one of the plan year even though you fund it gradually through payroll deductions.

You can only change the number mid-year after a qualifying life event, which is why a thoughtful estimate matters. Funds are use-it-or-lose-it unless your plan offers a small rollover or grace window.

  • Contributions come out pre-tax, so $1,000 in your FSA can feel like $1,300 in take-home money.
  • Most plans reimburse after you submit proof of purchase; some offer debit cards but still require receipts later.
  • Human resources administers the account, but the rules flow directly from IRS Publication 502.

Remember

An FSA is not the same as an HSA. HSAs roll over and belong to you forever; FSAs are tied to your employer and reset each plan year.

Scope

What actually counts as an eligible expense

The IRS cares about medical necessity. That often includes mundane items you already buy on Amazon, in pharmacies, or at specialty retailers.

Think beyond co-pays. Eligible categories range from contact solution to fertility tracking devices. The key is whether the product diagnoses, treats, prevents, or mitigates a medical condition.

  • Over-the-counter care: pain relievers, antacids, cold & flu meds, allergy relief, first-aid kits.
  • Everyday wellness: sunscreen SPF 15+, menstrual care, prenatal vitamins, compression socks, thermometers.
  • Therapy & recovery: TENS units, percussive massage guns, orthopedic supports, at-home PT tools.
  • Services: therapy visits, chiropractic sessions, dental work, vision exams, prescription eyewear.

Grey areas

Items that can be considered “general health” sometimes need a Letter of Medical Necessity (LMN) from a provider. FSA Helper tracks which purchases fall into that bucket.

Proof

Documentation administrators actually want

Fast reimbursements come from clean documentation. Administrators are optimizing for audit trails, not aesthetics.

Expect to supply a receipt or statement that lists the merchant, date, amount, description, and proof of payment. Screenshots of Amazon orders work, but administrators prefer consolidated PDFs so reviewers do not chase URLs.

If a product needs an LMN, attach a signed note from a licensed provider that states the medical condition and why the item is necessary.

  • One file per claim keeps back-and-forth low—combine receipts, LMNs, and claim forms.
  • Use consistent naming (e.g., “2025-02-Navia-Claim.pdf”) so you can reference submissions later.
  • Save documentation in a synced drive or inside FSA Helper to keep an audit trail.
System

A simple quarterly workflow

Most people scramble in December because they only think about their FSA once a year. A light ritual removes the panic.

Month 1: Import recent purchases, label what is eligible, and capture receipts while they are easy to find.

Month 2: Generate a running claim (even if you do not submit yet) to see how much money is sitting on the table.

Month 3: Submit anything over a threshold—say $200—so cash keeps flowing back to you.

  • Put a 20-minute recurring block on your calendar. Treat it like paying a bill.
  • Use the grace period (if offered) to mop up items bought right after the new year.
  • During open enrollment, compare last year’s eligible spend against the next year’s election.
Product

Where FSA Helper slots into the process

We built FSA Helper because collecting receipts, filling PDFs, and tracking LMNs felt like ten different tabs. The product handles the annoying steps so you can focus on caring for yourself.

The browser extension imports Amazon orders automatically and flags likely eligible line items using medical tax codes. You can connect additional sources as we roll them out.

We pre-fill Navia claim PDFs (Fidelity support is in progress) with your member profile, totals, and receipts attached in the format reviewers prefer.

For LMN-required items, we give you templated letters you can route to your provider for signature, then store alongside the matching purchase.

  • Dashboard insights tell you how much is claimed, pending, or still unsubmitted.
  • Storage paths in Supabase keep every claim packet organized by sanitized email so you can reference them later.
  • The upcoming “Academy” section will reference articles like this one directly inside your workflow.

Next step

Put this guide to work in minutes

Create a free FSA Helper workspace, connect your Amazon account, and watch eligible purchases organize themselves into ready-to-send claim packets.

Launch FSA Helper