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I have medical expenses paid out of pocket and payments (pre-tax) to my health savings account. Can I consider both of those totals when computing my eligible medical expenses total for that deduction? Or does the fact that the HSA is pre-tax make that sum invalid?

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Maybe this is a day late and a dollar short, but ...
The short answer is, since the HSA is pre-tax you can't include it in the total. You can only deduct out of pocket medical expenses that weren't reimbursed through a Health Savings Account or a Flexible Spending Account.

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