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PaperclipPerfector  1mo ago (text post)   2090 thread views

Small-Scale Question Sunday for September 28, 2025

Do you have a dumb question that you're kind of embarrassed to ask in the main thread? Is there something you're just not sure about?

This is your opportunity to ask questions. No question too simple or too silly.

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I am not very up on Roth stuff, but wpuld things change if receipt storage were completely trivial? The way my, and I assume nearly all, HSA works is that I submit receipts to the conpany that manages the HSA, and then those credits for withdrawal and ready for me whenever I want to use them. There is no receipt tracking because I just submit immediately.

would things change if receipt storage were completely trivial

Not much. Receipt storage is nearly trivial anyway. There's still a financial advantage to my strategy for anyone who doesn't fully exhaust their HSA by the time they die (as well as anyone who doesn't expect to fully exhaust their HSA by age 60, and isn't currently saturating every Roth contribution channel), I claim.

I submit receipts to the conpany that manages the HSA, and then those credits for withdrawal and ready for me whenever I want to use them

You're liable to show your receipts to the IRS in case of an audit, which could be up to 7 years after you get reimbursed / make the withdrawal. Are you sure you'll be using this HSA provider for that long? If you're burning your paper copies, you're vendor-locking yourself.

And, if you are delaying your withdrawals (so-called shoebox strategy, the topic at hand), are you sure your HSA provider keeps receipts for 7 years after the withdrawal date, not just 7 years after you submitted the receipt?

Yes, I am 100% sure that HSA providers used by big companies have procedures that will guarantee everything is fine forever. I'm more interested by the financial argument than a receipts argument.

anyone who doesn't fully exhaust their HSA by the time they die

Is that actually a meaningfully large group of people? I spend something like half to 2/3 of my annual HSA contribution every year, and I'm only 40. Odds are very strong that I'll empty the thing before I die, because my healthcare costs will go up and I won't be contributing any more. I didn't get the impression that I was a particularly isolated case, either.

Odds are very strong that I'll empty the thing before I die

Even if you expect to exhaust your HSA before you die, my proposed strategy still either beats or ties the “shoebox strategy” as long as you anticipate your HSA lasting through age 60, you're currently under 59, and you're not currently maxing out your Roth contributions.

If your older-than-60 self incurs medical expenses at least 7.5% of your gross income and itemizes, those expenses can be deducted—unless you used them as an excuse to make a tax-free HSA withdrawal. So if your future self is going to need the growth on today's existing HSA dollars to pay for medical expenses, you will still be better off burning any at-hand receipts to make HSA withdrawals today and coincidentally making Roth contributions of an equal amount. (And during years your future self is spending less than 7.5% of gross income on medical expenses, or fails to itemize, my proposed strategy does no worse than the “shoebox strategy”—you're still making 100% tax-free withdrawals from growth on money your past self had put into an HSA.)

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