I have not had an HSA before, so new to this. I am retired and receive a monthly pension payment. Out of that payment comes my healthcare premiums, state and federal taxes. The administrator for the pension says they cannot redirect just part of my remaining pension payment to an HSA account. How then do people fund their HSA? The HSA account people said I can contribute with after tax money, then deduct those contributions on my taxes. If that's the case, can I contribute say $500 monthly, then a few days later pull that money out to pay for my medical premiums? Sounds crazy but perhaps that's the game you have to play.