@dadgad5651 it's not really a grey area. Double-dipping isn't allowed when it comes to federal income taxes.
So, you can have medical expenses reimbursed from an HSA. And you can deduct them on your tax return. But you can't do both with the same expense. If you've already gotten an HSA reimbursement for any particular expense (or if you used your HSA to pay for it, same thing), you can't include it in your total medical expenses on your Schedule A, unless you first have it reversed by filing the relevant paperwork with your HSA custodian. Conversely, once you file your tax return, you can't take an HSA reimbursement for any expenses you've already deducted on your Schedule A.
Obviously, it's pretty easy to make mistake here, so there are ways of correcting it once it's discovered. But it's still not allowed.
