A Roth conversion is not clever. It is arithmetic. You take money that will one day be taxed, you pay the tax now at a rate you can see, and you never pay tax on it again. The debate is entirely about which years to do it in.

The window everyone misses: the years between when your paycheck ends and when Social Security or RMDs begin. Your marginal rate is often ten to fifteen points lower than it was a year ago and will be a year from now. That gap is the whole game.

A modest conversion in each of those years — enough to fill the current bracket but not push into the next — can quietly move six figures of eventual taxes off the table. It won't feel like anything. That's the point.

This is genuinely a case where a one-hour conversation with a fee-only CPA pays for itself many times over. Ask specifically about the bracket-filling strategy. If they don't know what you're talking about, find a different CPA.