It sounds like he means there isn't enough money in the HSA from payroll deductions to cover the medical bills he has. That is my situation too. If I add to the HSA balance from my after-tax checking account funds it sounds like I will get a deduction, if I itemize on my tax returns. With the new higher standard deduction, if my itemized items are less than the standard deduction then I won't itemize and won't see any tax benefit from making an additional contribution to HSA from my checking account. Is that right?
