IRS Guidelines for Reimbursements
Medical expenses incurred before a self-insured reimbursement plan is established cannot be reimbursed tax-free. See what IRS rules say about taxable income.
REIMBURSEMENTSSIMRPLEGAL
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Short answer: Medical expenses incurred before a self-insured reimbursement plan is established cannot be reimbursed tax-free. See what IRS rules say about taxable income.

IRS Guidelines for Reimbursements Under a Self-Insured Medical Expense Plan
Can an employee exclude reimbursements from taxable income if those medical expenses were incurred before their employer officially set up a self-insured medical reimbursement plan?
The Situation
Employer X sets up a self-insured medical reimbursement plan on December 1. The plan says it’s “effective” retroactively from January 1 of the same year. Employee A joins the plan on December 1 but had medical expenses earlier in the year, before the plan actually existed. Employee A submits those earlier expenses, and the employer reimburses them.
The Law
Generally, all income is taxable unless there’s a specific exception. Section 105 of the IRS Code says medical reimbursements are not taxable if:
They’re paid under a valid accident or health plan, and
They reimburse the employee, spouse, or dependents for actual medical care.
But here’s the key: the plan must already be in place at the time the expenses were incurred.
Court & IRS Findings
Past IRS rulings and court cases (like American Family Mutual Insurance Co. v. U.S. and Wollenberg v. U.S.) have made it clear:
A plan cannot be made “retroactive” to cover expenses from before it was created.
Reimbursing expenses incurred before the plan existed makes those payments taxable income.
The Ruling
Reimbursements for medical expenses incurred before the plan was established are not excludable under Section 105(b). In other words, the employee has to count those reimbursements as taxable income.
Plain takeaway: You can’t set up a medical reimbursement plan today and use it to cover medical expenses from earlier in the year. Only expenses incurred after the plan officially starts qualify for tax-free treatment.
This article is based on an article published on taxnotes.com, you can view the article and its author information HERE.
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Educational only, not tax advice. This page is a general explanation and is not tax, legal, or accounting advice. Every organization is different, so talk with a qualified tax professional about your plan.
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