Should You Convert Your Entire IRA to Roth? (How to Find Your Real Window)

For years the entire Roth conversion conversation ran on one deadline: convert before 2026, because tax rates were scheduled to jump. Then the 2025 tax law made the current brackets permanent and that countdown disappeared, so most people concluded there's no rush. That may be the wrong conclusion, because Washington's deadline was never the one that mattered. The one that decides this sits on your own income timeline, and almost no one thinks to look at it. We break down the 2025 law itself in our video on the One Big Beautiful Bill.

1. The earnings tail.

The year after he leaves, there's still around $250,000 landing: severance, a final bonus, RSUs still vesting, options being exercised, deferred comp on a schedule set years ago, consulting income, maybe a board seat, plus a working spouse. Add it up and they're still recognizing over $400,000. That first "retirement" year is a false window with almost no room to convert efficiently.

2. The income control window.

Once the spouse retires and the deferred comp and equity wind down, the baseline finally drops and he has real control over how much taxable income to recognize. This is where conversions, strategic withdrawals, and capital-gain decisions have room to happen. In this household it opens at 62 and starts closing at 70, when Social Security turns on. Eight years, and they nearly spent the first three thinking they were already in it.

3. The retirement income floor.

Social Security switches on, pensions or annuities may start, and eventually required distributions force money out of the pre-tax accounts whether it's needed or not.

Here's the whole thing in one sentence: your conversion window opens when the earnings tail ends and starts closing when the retirement income floor rises. This household's window has nothing to do with Congress and everything to do with their own calendar. Low-income years are the raw material of good conversion planning, which we covered in the silver lining of lower-income years.

The tax-savings number on its own is the least interesting part. A conversion in the open years is really buying four things:

Lower required distributions.

• Do nothing and it's $6.4M throwing off $230,000 a year you didn't ask for. Fill 24% and it's about $1.1M and $49,000. Convert it all and RMDs are zero.

Protection for whoever outlives the other.

• One spouse will likely file single for 5 to 10 years, same income but half the standard deduction and compressed brackets. In this model, if the survivor files single for 10 years, doing nothing costs about $156,000 a year in federal tax versus about $39,000 under the dynamic strategy.

A lower Medicare cost over time.

• Conversions raise your premiums in the years you convert, a real but temporary cost. Doing nothing cost this family about $164,000 in lifetime Medicare surcharges; the dynamic strategy cost about $106,000. Less, not more, even while deliberately spiking income for eight years.

What the children actually keep.

• Non-spouse heirs have 10 years to empty an inherited pre-tax account, often during their own peak-earning years. If the kids are in the 37% bracket, doing nothing leaves them about $14.1M while the best strategy leaves $15.6M, because once the pre-tax account is empty, their future bracket stops being your problem.

1. Map your entire income calendar.

• Every source, every year. You cannot find your window by looking only at your retirement date.

2. Find your taxable income capacity.

• Estimate taxable income before any conversion, then see how much room is left in your target bracket. Gross income, taxable income, and the number that drives Medicare are three different things.

3. Price the hidden costs.

• A conversion can raise state tax, increase how much of your Social Security is taxed, trigger Medicare surcharges two years later, phase out deductions, and cost you subsidies. Some states don't tax conversions after age 59 and a half, so check yours.

4. Compare the future household, not just this year's return.

• Model the surviving spouse in single brackets and what your heirs would actually inherit and pay.

5. Confirm liquidity and time horizon.

• Where does the tax get paid from, will your taxable accounts still cover spending, and how long can the Roth money stay invested and grow?

6. Execute annually, not permanently.

• Income, markets, tax law, and even where you live can change. A target you set five years out should never be followed blindly.

Those are ways to get new money into a Roth each year through contributions. A conversion moves money you already have in a pre-tax IRA or 401(k) into a Roth and pays the tax now. They can work together: our guide to the mega backdoor Roth in 2026 covers the contribution side.

This is for executives in their 50s and early 60s with a large pre-tax balance (often $1 million or more), a complex earnings tail of severance, deferred comp, and equity, and a retirement date on the horizon. If that's you, the deadline that matters isn't in the tax code, it's on your own income calendar, and the years between your last big paycheck and your first Social Security check are the most valuable planning window you'll get. The move that closes this window for good, timed wrong, can cost seven figures. Related reading on timing that income floor: taking Social Security at 62 vs 70.