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The general rule is that only expenses incurred after you first funded the HSA will be eligible for tax-free medical reimbursement. Full details: https://www.newfront.com/blog/hsa-establishment-date General HSA Establishment Rule: Ability to Incur Expenses That are Eligible for Tax-Free Medical Distributions Does Not Begin Until HSA is Funded Individuals may take a qualified tax-free medical distribution from an HSA only for medical expenses incurred after the individual established the HSA. State trust law determines when an HSA is considered “established.” Most state laws require that a trust be funded to be established. This means that in most cases an HSA is not established until a contribution is deposited. Example 1: – Aaron is hired November 15 by Cheese heads, Inc. with date of hire coverage. – Aaron enrolls in the company’s HDHP medical plan option. – Aaron did not establish an HSA previously. – On November 20, Aaron incurs $250 in deductible expenses under the Cheese heads, Inc. HDHP medical plan option. – The first deposit into Aaron’s HSA is made by Cheese heads, Inc. in December. Result 1: – Aaron’s HSA is established in December. – Aaron cannot use the HSA to pay for his $250 deductible expenses on a tax-free basis because they were incurred prior to the December establishment of the HSA. – Important Note: Aaron also is not HSA eligible (i.e., eligible to make or receive HSA contributions) in November because he was not covered by the HDHP as of the first day of the calendar month.