I have underfunded my HSA last year and this year. You cannot modify this until the end of the year "Open Enrolment". However, not having enough in the account, I was forced to make purchases from bank card toward pharmacy prescription drugs. Can I simply take the receipts which I made through my Bank Card to "Walgreens" for drugs and apply it to "HSA Contributions" vs. going through some kind of contribution which will be after tax. Do I specifically need to contribute after Tax to the account only to withdraw it for reimbursment? Then the entry on "Any contributions you personally made(not through your employer) would qualify? Right?