Your HSA keeps asking for more documents. Here's what to send.

Short answer

First, work out which account is asking. If your card also draws on an FSA or HRA, those accounts have their own proof rules, and the request may be coming from one of them. Then send exactly what the request names: usually an itemized receipt, plus the EOB or letter of medical necessity (LMN) that matches it. Keep a copy of everything you send, filed with the expense.

Why you're getting asked

Start with the rule most people don't know. For a true HSA, the IRS doesn't make your custodian check your spending. Notice 2004-2, Q&A 29 says: "HSA trustees or custodians are not required to determine whether HSA distributions are used for qualified medical expenses. Individuals who establish HSAs make that determination and should maintain records of their medical expenses sufficient to show that the distributions have been made exclusively for qualified medical expenses and are therefore excludable from gross income."

Not required to check is different from not allowed to ask. A request usually traces back to one of three places, and the fix is different for each.

1. Your card also pays from an FSA or HRA

Health FSAs and HRAs run on stricter proof rules than HSAs. IRS Publication 969 says that for a health FSA: "You must provide the health FSA with a written statement from an independent third party stating that the medical expense has been incurred and the amount of the expense. You must also provide a written statement that the expense hasn't been paid or reimbursed under any other health plan coverage."

Cards work inside those rules. Pub 969 again: "Debit cards, credit cards, and stored value cards given to you by your employer can be used to reimburse participants in a health FSA. If the use of these cards meets certain substantiation methods, you may not have to provide additional information to the health FSA." It says the same about HRA cards. That's why an FSA or HRA card swipe can come back to you as a request for paper.

The fix: find out which account actually paid for the transaction. If it was the FSA or HRA, answer with the third-party statement the plan asks for. An itemized receipt or EOB from the provider or insurer is the usual candidate, but follow the plan's instructions on what it accepts.

2. Your HSA custodian's own review

Your custodian can still have its own account rules or review flagged transactions. The IRS sources above don't describe those reviews, so the letter itself is your best guide. Read exactly what it asks for and answer that, nothing more.

The fix: send the itemized receipt for the transaction they named, and the EOB if insurance was involved.

3. A merchant or platform program

Some purchases come with their own paperwork step. Truemed, for example, says on its how it works page: "At checkout, select Truemed and complete a health survey. If you qualify, you'll receive your Letter of Medical Necessity and pay directly with your HSA/FSA card." If your administrator later asks about one of those purchases, the LMN and the itemized order are what you'll need. More on that below.

What usually satisfies a request

Match the document to the words in the request. Send what it asks for, not your whole file.

A card statement alone never answers a request. It shows that money moved. It doesn't show what you bought.

Keep the receipt, EOB and LMN together per expense so the next request is quick.

LMN and Truemed purchases

A letter of medical necessity is a note from a medical practitioner that ties a purchase to a medical condition. Wellness platforms such as Truemed build that step into checkout. Truemed's FAQ says: "An independent licensed practitioner reviews your information and, if appropriate, issues a Letter of Medical Necessity (LMN) based on your individual health needs."

Here is where the IRS draws its line. In IR-2024-65, it said: "Some companies mistakenly claim that notes from doctors based merely on self-reported health information can convert non-medical food, wellness and exercise expenses into medical expenses, but this documentation actually doesn't."

The IRS nutrition and wellness FAQ says what does count. For supplements: "Yes, but only if the supplements are recommended by a medical practitioner as treatment for a specific medical condition diagnosed by a physician." For a gym, it's only for a specific purpose such as treating a diagnosed disease, and "Otherwise, the cost of a gym membership is for the general health of the individual and is not a medical expense."

So the test that matters is the diagnosed condition. An LMN is strongest when it names a real diagnosis and the purchase treats it.

What Truemed itself says about administrators, from its FAQ: "Truemed provides the required documentation and works to support a compliant submission, but cannot override your plan administrator's final decision." And: "If a claim is denied, your administrator may request additional documentation or clarification." Truemed also says "Your Letter of Medical Necessity (LMN) is securely stored in your Truemed account," so that's where to download it if you need to send it.

The practical part. For every LMN purchase, keep three things in one place: the LMN, the itemized order, and a note of the condition it treats. Our Truemed HSA guide covers how the process works, and Truemed alternatives and Truemed vs Flex compare the options. For a specific case, see the LMN for GLP-1 question in HSA edge cases.

If you can't satisfy it

Sometimes the purchase didn't qualify, or the paperwork doesn't exist. You have two options.

Ask your administrator whether you can repay the transaction to the account. Pub 969 doesn't describe a repayment process, but Notice 2004-50 does, for one case. Q&A 37 lets you repay a distribution made "because of a mistake of fact due to reasonable cause," such as an expense you reasonably believed qualified, when there is "clear and convincing evidence" of the mistake. The deadline is April 15 following the first year you knew or should have known it was a mistake. Repaid that way, it isn't included in your income, the additional tax doesn't apply, and it isn't treated as an excess contribution. Q&A 76 says your custodian doesn't have to accept it ("No, this is optional"), so whether you can, and how, is still up to your administrator.

Or treat it as a non-qualified distribution. Pub 969 is plain about what that costs: "If you don't use a distribution from your HSA for qualified medical expenses, you must pay tax on the distribution. Report the amount on Form 8889 and file it with your Form 1040, 1040-SR, or 1040-NR. You may have to pay an additional 20% tax on your taxable distribution." The exceptions: "There is no additional tax on distributions made after the date you are disabled, reach age 65, or die."

If the transaction was paid from an FSA or HRA instead, the HSA rules above don't apply, and the plan's own rules decide what happens. Ask the plan. For larger amounts, a tax pro is worth the call.

Stop repeat requests

• Keep HSA spending and FSA spending apart. If you have an FSA or limited-purpose FSA next to your HSA, know which card or account pays for what, so HSA purchases don't get pulled into FSA proof rules.
• Pay out of pocket and reimburse yourself later from a clean file. The HSA shoebox strategy explains the approach, and HSA debit card vs reimbursement compares the two habits. The full reimbursement rules cover what to keep.
• Keep one folder per expense: receipt, EOB, LMN if there is one, proof of payment. When a request comes, you forward the folder.

Keep one record per expense with the proof attached, and the next request takes one forward.

FAQ

Missing the receipt they want? See lost or faded HSA receipts for how to rebuild it. More on the term itself: substantiation.

Sources

• IRS Notice 2004-2, Q&A 29, Internal Revenue Bulletin 2004-2: https://www.irs.gov/irb/2004-02_IRB
• IRS Notice 2004-50, Q&A 37 and Q&A 76, Internal Revenue Bulletin 2004-33: https://www.irs.gov/irb/2004-33_IRB
• IRS Publication 969, Health Savings Accounts and Other Tax-Favored Health Plans: https://www.irs.gov/publications/p969
• IRS news release IR-2024-65 (March 6, 2024): https://www.irs.gov/newsroom/irs-alert-beware-of-companies-misrepresenting-nutrition-wellness-and-general-health-expenses-as-medical-care-for-fsas-hsas-hras-and-msas
• IRS, Frequently asked questions about medical expenses related to nutrition, wellness and general health: https://www.irs.gov/individuals/frequently-asked-questions-about-medical-expenses-related-to-nutrition-wellness-and-general-health
• IRS, How long should I keep records?: https://www.irs.gov/businesses/small-businesses-self-employed/how-long-should-i-keep-records
• Truemed, How it works: https://www.truemed.com/how-it-works
• Truemed, FAQ: https://www.truemed.com/faq