The Roth conversion window opens the year your paycheck stops and closes when required minimum distributions begin at 73, or 75 if you were born in 1960 or later. Convert enough each year to fill a target tax bracket without spilling into the next one, then scale back once Social Security and RMDs start refilling your income on their own.
What is the Roth conversion window?
Most executives spend their working years in a high bracket, then retire into a stretch with no salary, no pension yet, and Social Security still unclaimed. That gap is the window. RMDs begin at 73 under current law, or 75 if you were born in 1960 or later. The IRS sets each one by dividing your account balance by a life expectancy factor, and once they start you no longer choose how much comes out of the pre-tax account each year. See the RMD exposure guide for how that balance builds. The window is the only stretch of retirement where you, not the IRS’s schedule, set the size of the taxable withdrawal.
How much should you convert each year?
Fill the bracket, do not jump it. Federal brackets run 10%, 12%, 22%, 24%, 32%, 35%, and 37%, and the goal most years is converting up to the ceiling of a target bracket without crossing into the next one. Say a couple’s income after retiring, before any conversion, sits near the bottom of the 22% bracket from interest and a small pension. Converting enough to reach the top of the 24% bracket, and stopping there, uses the available room without paying 32% on any of it. Do this every year the window stays open, and a meaningful share of a large pre-tax balance moves to Roth on a schedule you chose. These are illustrative brackets and figures, not a projection for any specific household.
State residency during those years matters as much as which bracket you fill. A conversion done while still a resident of a state with its own income tax pays that state tax on top of the federal bill, due the same April. The identical conversion done after a move to a state with no income tax on retirement withdrawals does not. Executives relocating in retirement sometimes have real control over which side of that move a large conversion falls on, and the sequencing deserves the same attention as the federal bracket math.
How does the window shrink as the years pass?
The window does not stay the same size from the day you retire to the year RMDs begin. Each income source that switches on eats into the room available for conversion.
| Stage | What turns on | Effect on conversion room |
|---|---|---|
| Retirement to 62 | Paycheck stops, no Social Security yet | Widest room in the window |
| 63 to 64 | Same, but this stretch sets Medicare’s first premium | Wide, watch the IRMAA lookback |
| 65 to 69 | Medicare premiums active, Social Security optional | Narrower, provisional income now in play |
| 70 | Delayed Social Security reaches its maximum | Narrower still |
| 73 or 75 onward | RMDs begin | Window closed |
What happens if you convert too much in one year?
Cross into the next bracket and you pay a higher marginal rate on the excess for no added benefit. Cross an IRMAA threshold and a conversion two years ago can raise this year’s Medicare premium. Cross the provisional income threshold with Social Security already claimed and up to 85% of that year’s benefit becomes taxable, on top of the tax owed on the conversion itself. A conversion sized well on paper in January can still overshoot if a bonus, a stock sale, or an NQDC distribution lands in the same year.
How does this fit into the rest of your plan?
A conversion strategy decided alone tends to fight the rest of the plan. Delaying Social Security to 70 opens more bracket room in the early conversion years, since no benefit is counting against provisional income yet, but the larger benefit that arrives at 70 narrows the window from the other end. Retiring before 65 adds a third variable: a large conversion year can also raise household income enough to shrink an ACA premium tax credit during the health insurance bridge to Medicare. None of these decisions moves in isolation.
What should you do next?
Project income for every year of the window before converting anything, not just the current year. Pick a bracket ceiling to convert to and revisit that number each year as pensions, Social Security, and account values change. Set aside outside cash to cover the conversion tax so the IRA balance being converted stays whole.
A conversion schedule only works if it accounts for RMDs, IRMAA, and Social Security at the same time. Schedule a consultation to see how the window fits your numbers.
Common questions
- Do you pay tax on a Roth conversion right away?
- Yes. The converted amount counts as ordinary income in the year you convert. Pay that tax from savings outside the IRA, not from the converted funds themselves, or you shrink the balance you are trying to grow tax-free.
- Can you undo a Roth conversion once you make it?
- No. Recharacterization, the old way to reverse a conversion, ended with the 2017 tax law. Model the conversion amount before you execute it, since the decision is final for that tax year.
- Does a Roth conversion affect Social Security taxation?
- Yes, in the year you convert. The converted amount adds to provisional income, which can push more of that year’s Social Security benefit into taxable territory if benefits have already started.
- What is the five-year rule for Roth conversions?
- Each conversion starts its own five-year clock for penalty-free access to the converted principal before age 59½. After 59½, that particular rule no longer applies, though a separate five-year rule still governs whether earnings come out tax-free.
- Should a couple convert the same amount every year?
- The right amount changes as pensions, Social Security, and deferred compensation phase in and use up bracket room a conversion would otherwise fill. Revisit the number every year rather than setting it once.
If the decisions on this page are ahead of you, the two of you can work through them with Robert Boeck before any of them becomes permanent.
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