re: HRA and how to use it?

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expenses I have paid out of pocket for in the last 18 months.

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I am not sure if you can back pay a previous year's expenses with an HRA unless they were incurred last year and you paid them this year. You may want to check with someone before moving forward with that. I know the IRS can put up to a 20% penalty on non-eligible expenses reimbursed through an HRA.