Roth Conversions

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

Written by Dan PasconeJuly 21, 2026

Why would someone with a seven-figure IRA voluntarily hand the IRS the single biggest tax bill of their life, all in one year? Sometimes there's a real reason. The video above walks through the full model.

TL;DR

Converting your whole IRA to Roth in one year is occasionally brilliant and usually not. The deadline that matters was never Washington's, it's your own income calendar. Your conversion window opens when your earnings tail ends and starts closing when Social Security and required distributions turn on, and for many executives that window is only about eight years.

- The 2026 tax-rate sunset was removed, so there's no forced national deadline, but that does not mean there's no rush for you.

- Most executives misread the first few years after leaving work as their low-income window. It usually isn't, and that mistake is expensive.

- "Always convert" and "never convert" are both guesses. The only answer comes from modeling the surviving spouse and the heirs, not just this year's return.

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.

The example we'll model

To make this concrete, picture an executive aged 58, married, spouse age 56. He's leaving his corporate role at the end of this year, and the household brings in about $1.1 million across salaries, bonus, and equity. They hold $3 million in pre-tax accounts, about $450,000 in a Roth, roughly $1.5 million in an after-tax brokerage, and some cash.

If they do nothing, that $3 million grows untouched for about 15 years until required distributions start at age 73, reaching roughly $6.4 million in today's dollars. The first year's required distribution alone is about $230,000, not because they need it, but because the IRS says so. Over their lifetime, doing nothing costs this family about $3.4 million in taxes. That's the number sitting in front of them before anyone converts a single dollar.

The three phases (and the false window that fools people)

Most people assume the fix is obvious: he retires, income drops, and next year he starts converting. Watch what actually happens to their income instead. Your traditional W-2 can stop long before your income does, and that gap is where the mistake lives.

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 five strategies, compared

A Roth conversion doesn't eliminate tax, it accelerates it, and under current law it generally can't be undone. So the question is rarely "can they afford the tax this year," it's whether paying now leaves the family with more after-tax wealth later. We modeled five versions for this household:

Strategy	Approx. tax cost	IRA left at 73	First RMD at 73

Do nothing	$0 now, ~$3.4M lifetime	~$6.4M	~$230,000
Fill the 22% bracket	~$260,000 over 11 years	~$4.6M	~$168,000
Fill the 24% bracket	~$700,000 over 11 years	~$1.1M	~$49,000
Dynamic (recalculated yearly)	lower effective rate (~14%)	~$2.2M	~$81,000
Convert the entire IRA at once	~$1.3M in one year (~36% effective)	$0	$0

The gap between the best version and the worst is about $1.7 million in today's dollars, and it keeps widening with age because the decision compounds. After-tax family wealth in this model runs about $7.7M vs $8.2M at age 73, $10.5M vs $11.4M at 82, and $13.9M vs $15.6M at 90.

What a conversion is actually buying

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.

What most people miss

The mistake that wrecks this before the math even starts is misreading the earnings tail as the income control window. Everyone pictures a clean line: last day of work, income drops, start converting. In reality the severance, deferred comp, vesting equity, consulting, and a working spouse keep the tax return full for years. In this household the real window didn't open until 62, and every year they waited was roughly $300,000 of conversion capacity they could never get back, because the window closes on a schedule they don't control.

The second thing people miss: the goal in the open years is not to pay the least tax this year. It's to use flexible years before less flexible income shows up again, and to protect the surviving spouse and the heirs. That is why "always convert" and "never convert" are both guesses. The only way to know is to model the future household, not just this year's return.

So, does converting the whole IRA ever make sense?

Converting everything sounds extreme because it is, but that doesn't automatically make it wrong. In this household it finished last: about $1.3 million in tax, an effective rate near 36% on every dollar, versus 14% for the dynamic approach. Same account, same family, two and a half times the price.

A full or very large conversion becomes more defensible when several things line up: an unusually low-income year, a huge share of wealth in pre-tax accounts, plenty of outside cash to pay the tax (not from the IRA itself), a surviving spouse who'll face compressed single brackets, and high-earning kids who'd inherit and empty the account during their peak years. It usually backfires when the earnings tail is still paying out and the conversion lands in the 35% or 37% bracket, when you'd pay the tax from the IRA itself, when you might move to a lower-tax state soon, when there's charitable intent that could use those pre-tax dollars efficiently later, or when the whole idea is driven by fear of taxes instead of an actual model.

Six steps to find your own window

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.

Frequently Asked Questions

Should I convert my entire IRA to Roth in one year?

Usually not, but occasionally yes. In the household we modeled, converting everything finished last, costing about $1.3 million in tax at a roughly 36% effective rate. It becomes defensible only when several factors align at once: an unusually low-income year, most of your wealth in pre-tax accounts, outside cash to pay the tax, a surviving spouse facing single brackets, and high-earning heirs. The honest answer is that a full conversion is one scenario to compare against the others, not a default.

When is the best time to do Roth conversions?

In your income control window, the stretch after your earnings tail (severance, deferred comp, vesting equity, consulting) winds down but before Social Security and required distributions push your income back up. For many executives that window is roughly age 62 to 70. The timing is personal, which is why at Tailored Wealth we map your income calendar year by year before recommending any conversion amount.

Is it worth converting at 24% if my future rate might be 22%?

It can be. The point of converting isn't only to beat your own future bracket, it's to get real money out before required distributions start and to protect your spouse and heirs. In our example, filling the 24% bracket beat filling 22% by almost $1 million once the surviving-spouse and inheritance math was included. You only see that by modeling the whole household.

Does a Roth conversion raise my Medicare premiums?

Yes, in the years you convert, through the income-related surcharge that shows up about two years later. But it is often a temporary cost that buys a permanently lower income floor. In our model, the strategy that deliberately spiked income for eight years still ended up with lower lifetime Medicare surcharges than doing nothing, because required distributions later were so much smaller.

How is this different from a backdoor or mega backdoor Roth?

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.

Who this is for

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.

Book a Free Wealth Strategy Call

If you want to see where your own tax control window opens and closes, mapped against your income calendar, bracket capacity, and surviving-family picture, that's exactly what we do. It's a low-friction conversation about your situation, not a sales pitch.

Disclosure

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