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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.

Culture war topics are accepted, and proposals for a better intro post are appreciated.

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I assume some of the people discussing this…

That's the thing, though—I have never once (before today) seen Roth accounts mentioned in the context of this.

Of the first page of Google results for shoebox hsa strategy, every article, including a YouTube video and the Reddit thread, fails to mention either my Roth-sweep strategy or the growth-death strategies as alternatives to the shoebox strategy; only the Bogleheads Forum thread even makes mention of my Roth-sweep strategy. (HowToMoney gets half credit for at least suggesting the idea of maxing out your Roth contributions before you put anything in your HSA; but they still don't even touch on my claim about how you could do a lot better than the shoebox strategy with existing HSA-eligible receipts.)