Where I work (maybe anywhere) you have to be psychic in order to take advantage of a HSA. So if you have money left over at the end of the year, the manager (government?) can keep it. So don’t think of draining your account by buying tylenol, aspirin, etc.
You can do what I do and look at your out of pocket expenses from the year before. I am lucky because my insurer participates in a paperless program. They forward medical bills to my FSA office and the money is direct deposited into my account. I don’t do anything, but watch the total claims agains the FSA and make sure I’m on glideslope.
I think you are describing a Flexible Spending Account.
I had a pre-tax account years ago as you describe, use it or lose it. Our HSA’s now though, can be continued into the next year, like a bank account.
I already went and stocked up on bandaids, dressings, etc. because I knew this was coming. (Those have no expiration dates either)
Looks like I’ll be stocking up at least on some things that do have expirations dates. Freakin’ g-d gubmint!!!