<prompt> Human: Hi there. Ive had an hsa since February 2014 but my office screwed up the auto debit into my HSA account. It currently has 0. Im about to be billed 1000 for a medical procedure. Can I somehow feed personal already taxed funds into this account and deduct them later? Kinda confused about my options or if there are rules against this.  <response>: As long as you are enrolled in an eligible HDHP plan, you can contribute any amount up the max allowed, and then deduct that amount when you file your tax return. By not contributing directly from payroll, you lose out on Medicare and FICA deductions, but can still get income tax deductions regardless of how you contribute. 