Should I Do Roth Conversions During the Gap Years Before RMDs?
Last reviewed: July 2026
Yes, for most pre-retirees with large pre-tax balances, the gap years are the best window of your life to run a roth conversion strategy. The gap years are the stretch between when your paycheck stops and when required minimum distributions begin at age 73, and they are usually the lowest-tax-bracket window you will ever see. A smart roth conversion strategy uses that window to move pre-tax IRA or 401(k) money into a Roth, pay tax now at a rate you can see and control, and pull that balance out of the future RMDs that push so many retirees into higher brackets. For a couple in their early-to-mid 60s with most of their savings sitting in pre-tax accounts, converting just enough each year to fill a lower bracket is often the single most valuable tax move on the board.
On This Page
- Key Takeaways
- What Is a Roth Conversion Strategy, and Why Do the Gap Years Matter?
- Who Should Convert During the Pre-RMD Gap Years?
- How Much Should You Convert in a Single Year?
- How Do Conversions Affect Medicare IRMAA and Social Security?
- When Does a Roth Conversion Hurt More Than It Helps?
- How Do You Build a Multi-Year Roth Conversion Ladder?
- How Does the R.U.D.D.E.R. Method Apply to Conversion Planning?
- Frequently Asked Questions
- Ready to Map Your Gap Years?
- Disclosures
Key Takeaways
- The pre-RMD gap years let you pay tax on IRA money at a known, often lower rate before age 73 forces withdrawals.
- Roth conversions have no income limit and no annual cap, so the only real ceiling is the tax bracket you choose to fill.
- In 2026, a married couple can have up to $211,400 of taxable income and still sit inside the 22% bracket.
- Convert too much and you can raise Medicare premiums two years later, so each conversion's size matters as much as the decision.
- A multi-year roth conversion ladder beats a single large conversion almost every time.
About the Author: Jeff Judge, CFP®, AEP®, ChFC®, CLU® is Managing Partner of Chesapeake Financial Planners in Forest Hill, Maryland. He has been helping families and business owners in Harford County and the Baltimore metro area plan retirement tax decisions since earning his CFP® certification in 2013, by using Chesapeake Financial Planners’ signature process, the R.U.D.D.E.R. method™. The clients who save the most on lifetime taxes are rarely the ones with the best investments; they are the ones who used the gap years on purpose.
What Is a Roth Conversion Strategy, and Why Do the Gap Years Matter?
A roth conversion strategy is a plan to move money from a pre-tax account, like a traditional IRA or an old 401(k), into a Roth IRA, paying ordinary income tax on the converted amount in the year you do it. Once the money is in the Roth, it grows tax-free, comes out tax-free in retirement, and is never subject to required minimum distributions during your lifetime. According to the IRS, there is no income limit on conversions and no annual cap, which makes them very different from the annual Roth contribution that high earners often cannot make directly.
The gap years are what make the math work. Once you stop drawing a salary but before Social Security and RMDs fully ramp up, your taxable income often falls to its lowest point in decades. That dip is a pricing window. You can choose to recognize income now, voluntarily, at a rate you can calculate, instead of letting the IRS dictate the rate later through forced withdrawals. The required beginning age is now 73 for anyone born between 1951 and 1959, and it rises to 75 for those born in 1960 or later under the SECURE 2.0 Act, which actually widens the gap-years window for younger pre-retirees.
Jeff Judge often tells clients the gap years are a sale on taxes that almost nobody shops. The tax code rarely lets you pick your own rate. For roughly the decade between retirement and your required beginning date, you can. That window does not reopen, and once RMDs start, the IRS sets the minimum income floor for you.
What counts as a "gap year"?
A gap year is any year after your earned income drops but before large mandatory income sources kick in. For most people that means the period from retirement (often early-to-mid 60s) until RMDs start, minus any years you begin Social Security early. These roth conversion gap years are valuable precisely because your bracket is low and you control how much income to add. A 63-year-old who retires and delays Social Security to 70 may have seven full gap years; that is seven separate chances to fill a low bracket on purpose rather than one rushed decision.
Why is a Roth balance worth more than a traditional balance of the same size?
A dollar in a Roth is worth more than a dollar in a traditional IRA because the Roth dollar is already tax-paid. A $500,000 traditional IRA carries a hidden tax bill that belongs to the IRS; a $500,000 Roth is entirely yours. That difference also matters for heirs, because under the SECURE Act 10-year rule, most non-spouse beneficiaries must drain an inherited account within ten years. Draining a pre-tax account on that timeline can land your children in their peak earning years' top brackets. inherited IRA 10-year rule
Who Should Convert During the Pre-RMD Gap Years?
The strongest candidates are pre-retirees who expect to be in the same or a higher tax bracket once RMDs and Social Security stack on top of each other. If you have a large traditional IRA or 401(k), a multi-year low-income window, and cash outside the IRA to pay the tax, a roth conversion before 73 usually pays off. The classic profile is a couple who retired at 63 with most of their savings in pre-tax accounts and a few years before benefits begin.
Conversions matter most for people whose future RMDs will be large. A $1.5 million traditional IRA does not stay quiet. The first RMD at 73 is roughly 3.77% of the prior year-end balance under the IRS Uniform Lifetime Table, and the percentage climbs every year after, often landing on top of Social Security and pushing otherwise comfortable retirees into the 24% or 32% bracket. Converting during the gap years shrinks that future balance before it can do damage. This is the part of planning where the math compounds quietly in your favor: every dollar you move out of the pre-tax bucket today is a dollar that never shows up as a forced withdrawal later.
The people who should be cautious are those who expect a genuinely lower bracket in retirement, those who will rely on the IRA for spending in the next few years, and anyone who would have to pay the conversion tax from the IRA itself. Charitable retirees are a special case. If you plan to give heavily in retirement, qualified charitable distributions can satisfy RMDs tax-free starting at 70½, which can make aggressive conversions less necessary. The decision is never one-size-fits-all, and the right answer depends on the specific shape of your accounts and your income.
Across hundreds of gap-year conversations, the pattern Jeff Judge sees most often is hesitation in the wrong direction. Clients fixate on the tax bill they will write this April and ignore the much larger bill the IRS will write for them at 73. The number on this year's return feels real because you pay it now. The number waiting at 73 feels abstract until the first RMD lands and a comfortable retirement suddenly looks like a high-income year you did not choose.
Does a Roth conversion make sense if I'll be in the same bracket in retirement?
Often yes, even at the same bracket. A conversion still removes future RMDs, reduces the share of Social Security that gets taxed, and leaves heirs a tax-free account instead of one carrying a built-in tax bill under the 10-year inherited IRA rule. Tax-rate arbitrage is the headline benefit, but it is not the only one. The Roth also gives you a tax-free bucket to draw from in a future high-income year, which is a flexibility a traditional IRA can never offer. What Is the Difference Between Marginal and Effective Tax Rate?
How Much Should You Convert in a Single Year?
Convert enough to "fill" your current bracket, but not so much that you spill into the next one. Filling the bracket means topping up your taxable income to the very top edge of the bracket you are comfortable paying, then stopping. In 2026, the IRS inflation-adjusted brackets give a married couple filing jointly a 22% bracket that runs to $211,400 of taxable income, with the standard deduction of $32,200 sitting on top of that. That deduction means a couple can recognize roughly $243,600 of gross income before a single dollar reaches the 24% bracket (assuming the standard deduction and no other above-the-line adjustments).
Here is the 2026 married-filing-jointly map, the one we draw on a whiteboard with nearly every gap-year client:
| 2026 taxable income (married filing jointly) | Marginal rate |
|---|---|
| $0 to $24,800 | 10% |
| $24,801 to $100,800 | 12% |
| $100,801 to $211,400 | 22% |
| $211,401 to $403,550 | 24% |
| $403,551 to $512,450 | 32% |
| $512,451 to $768,700 | 35% |
| $768,701 and up | 37% |
Say that couple has $40,000 of other taxable income in 2026. The top of the 22% bracket is $211,400, so they have about $171,400 of room to convert at 22% or less before touching the 24% bracket. Convert $171,000 and the whole amount is taxed at 22% or below. Convert $200,000 and the last slice jumps to 24%. The difference is real money, and it is entirely under your control. On a $28,600 overage, the bracket jump from 22% to 24% costs an extra $572 you never needed to pay.
What is "filling the bracket"?
Filling the bracket is converting just enough to reach the top of a target tax bracket without crossing into the next one. It turns a vague "should I convert?" into a precise annual number. The roth conversion ladder built this way, one bracket-filling conversion per year across the gap years, is how you move a large IRA into a Roth without ever paying a top-bracket rate on it. The discipline is in the stopping point, not the starting point. Roth conversion ladder explained
Should I ever convert past the 24% bracket on purpose?
Sometimes, yes. If your projected RMDs at 73 will land you permanently in the 32% or 35% bracket, paying 24% now can still be the cheaper rate over your lifetime. The question is never the rate in isolation; it is the rate today versus the rate you will be forced to pay later. A couple staring at $200,000 of mandatory RMD income in their late 70s may rationally fill the 24% bracket every gap year to avoid a worse outcome. How Can I Reduce Taxes When Earning $200K to $500K?
How Do Conversions Affect Medicare IRMAA and Social Security?
A conversion raises your income for the year, and two systems watch your income closely: Medicare and the taxation of Social Security benefits. This is where oversized conversions quietly backfire, and it is the part most do-it-yourself plans miss entirely.
Medicare uses your modified adjusted gross income from two years prior to set your premiums. For 2026, the Centers for Medicare & Medicaid Services set the standard Part B premium at $202.90 per month with a $283 annual deductible, and the first income-related surcharge (IRMAA) begins once MAGI passes $109,000 for a single filer or $218,000 for a married couple. A conversion that pushes you one dollar over a threshold can raise both spouses' premiums for a full year. The surcharge is a cliff, not a ramp, so planning around the brackets matters. Cross the line by a single dollar and you pay the full tier, not a prorated slice of it.
Social Security adds a second layer. As more income lands on the return, a larger share of your benefits becomes taxable, up to 85%, a threshold the Social Security Administration confirms applies to a growing share of beneficiary families over time. A conversion done before you claim benefits sidesteps much of this; a conversion done in a year you are already collecting can make the same dollars cost more. This is exactly why we often front-load conversions into the earliest gap years, before Social Security and Medicare are in the picture. The order of operations matters: do the heavy converting first, then turn on the income streams. Is Social Security Taxable? 2026 Tax Rules Explained How do you use the years between retirement and RMDs to reduce lifetime taxes? Jeff Judge notes: "We front-load the heaviest conversions into the earliest gap years precisely because once Social Security is on and Medicare IRMAA is watching your prior-year MAGI, the same conversion dollar carries a much higher total cost than it would have two or three years earlier."
Will a conversion raise my Medicare premiums?
It can, if the conversion pushes your MAGI above the IRMAA threshold for that year, and the effect shows up two years later. In 2026 the first surcharge tier starts at $218,000 of MAGI for married couples and $109,000 for singles. The fix is not to avoid converting; it is to size each conversion so you stop short of the threshold you care about. A two-year delay means a conversion at 63 first touches your premiums at 65, the year you enroll. What is a year-round tax planning calendar for retirees and pre-retirees?
When Does a Roth Conversion Hurt More Than It Helps?
A roth conversion strategy backfires when you pay the tax from the wrong place, convert in the wrong year, or convert more than your bracket can absorb. The biggest single mistake Jeff Judge sees is paying the conversion tax out of the IRA itself. Do that before 59½ and the withheld amount counts as an early distribution, adding a 10% penalty on top of the tax, and either way you shrink the very balance you were trying to make tax-free. The whole point is to maximize the dollars that land in the Roth, and paying the tax from the IRA defeats that purpose.
Timing is the other trap. A conversion in a high-income year, a year with a large capital gain, a severance payment, or a Roth done right before a known income spike, can cost far more than waiting twelve months. And unlike the old rules, a conversion can no longer be reversed. The IRS eliminated recharacterization of conversions under the Tax Cuts and Jobs Act, so the number you convert is final once the year closes. There is no undo button.
Here is the trade-off in plain terms:
| Approach | What you gain | What you risk |
|---|---|---|
| Convert during the gap years | Pay a known, often lower rate; smaller future RMDs; more tax-free money for heirs | Tax due now; possible IRMAA impact if oversized |
| Wait until RMDs begin | Keep cash now; no voluntary tax bill | Larger forced withdrawals at 73; higher brackets; more taxable Social Security |
The five-year rule is one more wrinkle worth knowing. Each conversion starts its own five-year clock, and withdrawing the converted principal before that clock runs and before 59½ can trigger the 10% penalty on that slice. For most gap-year converters in their 60s, this is a non-issue because they are already past 59½. For an early retiree in their 50s building a roth conversion ladder for income, it is central to the plan.
What is the single most expensive conversion mistake?
The most expensive mistake is paying the conversion tax from inside the IRA before age 59½, which both shrinks your tax-free balance and adds a 10% early-distribution penalty on the withheld amount. The second most expensive is converting in a year you already have a large one-time income event, stacking the conversion on top of a spike instead of waiting for a low-income year. How Can I Reduce Capital Gains Taxes on My Investments?
Can I convert too little?
Yes, and under-converting is a quieter mistake than over-converting. Leaving room in a low bracket unused every gap year is a permanent loss; that bracket space does not roll forward. A couple who converts $10,000 a year when they had room for $56,000 will arrive at 73 with a far larger pre-tax balance and far less of the gap-year window spent. Timidity has a cost too.
"I tell clients the gap years are a sale on taxes," Jeff Judge says. "You rarely get to choose the rate you pay the IRS. For about a decade, you can. Most people let that window close and then wonder why their RMDs feel like a second job's worth of income."
How Do You Build a Multi-Year Roth Conversion Ladder?
A multi-year roth conversion ladder is a plan to convert a bracket-filling amount each year across the entire gap-years window, rather than one large conversion in a single year. Spreading the conversions keeps every dollar in a lower bracket and keeps your MAGI under the IRMAA and Social Security taxation thresholds you care about. The ladder is the difference between paying 22% on a large IRA over eight patient years and paying 32% on it in one impatient one.
Start by mapping your projected income for every year between retirement and your required beginning date. For each year, identify the top of your target bracket, subtract your other taxable income, and the remainder is your conversion room. Convert into that room, watch the IRMAA line, and repeat. The plan flexes as life changes; a year with unexpected income gets a smaller conversion, a year with room to spare gets a larger one.
The roth conversion ladder also has a sequencing logic. Convert the most in the earliest years, before you claim Social Security and before Medicare premiums are in play. Each year a benefit turns on, your baseline income rises and your conversion room shrinks. A couple who front-loads conversions from 63 to 66 and then claims Social Security at 67 captures the cleanest, lowest-cost years of the whole window. tax-efficient fund placement
How many years should a conversion ladder run?
A conversion ladder typically runs the full length of your gap years, often seven to ten years for someone who retires in their early 60s and delays Social Security. The longer the runway, the larger the total balance you can move at a low rate. SECURE 2.0 pushing the RMD age to 75 for those born in 1960 or later adds even more years to work with. How can I potentially optimize my taxes as my income grows?
What should I do in a year my income is unexpectedly high?
In a high-income year, convert less or skip the conversion entirely, because stacking a conversion on top of a spike pushes the marginal dollars into a higher bracket. The ladder is meant to flex. A large capital gain, an inheritance, or a part-time consulting windfall are all reasons to pause for a year and resume when income normalizes. How will inheriting money affect my taxes this year?
How Does the R.U.D.D.E.R. Method™ Apply to Conversion Planning?
The R.U.D.D.E.R. Method™ is Chesapeake Financial Planners' six-step planning process: Review and Recognize, Uncover and Understand, Design and Develop, Discuss and Decide, Execute and Empower, and Reassess and Refine. A roth conversion strategy is rarely a one-time decision, which is exactly why it belongs inside a repeatable process rather than a single annual scramble.
In the Review and Recognize step, we map your pre-tax balances and project your RMDs and bracket at 73 to see how big the future problem actually is. Uncover and Understand surfaces the constraints, the cash available to pay the tax, the IRMAA thresholds, and your Social Security claiming plan. Design and Develop builds the year-by-year ladder. Discuss and Decide is where you set the bracket you are willing to fill. Execute and Empower runs the conversion, usually with deliberate timing in the fourth quarter once the year's income is clear. Reassess and Refine is the part most plans skip: every year the ladder gets re-checked against new brackets, new balances, and new life events.
That last step is why a conversion plan is never finished until your required beginning date arrives. Tax law changes, your portfolio grows, and a single year's market drop can create a discounted conversion opportunity worth seizing. A plan reviewed once and filed away is worth a fraction of a plan revisited every fall.
Frequently Asked Questions
Is there an income limit on Roth conversions?
No, there is no income limit on Roth conversions and no annual dollar cap. This is the key difference from a direct Roth contribution, which phases out at higher incomes. Anyone with a traditional IRA or eligible 401(k) can convert any amount in any year, regardless of how much they earn. The only practical limit is the tax bracket you are willing to fill.
What is the best age to start a Roth conversion ladder?
The best age to start a Roth conversion ladder is usually the first year your earned income drops, often the early-to-mid 60s, because that is when your bracket is lowest and your conversion room is largest. Starting before you claim Social Security and before Medicare premiums are set gives you the cleanest, lowest-cost years to move the most money at a known rate.
How does a Roth conversion affect required minimum distributions?
A Roth conversion permanently removes the converted balance from your future required minimum distributions, because Roth IRAs have no RMDs during the original owner's lifetime. Every dollar you convert before 73 is a dollar that never appears as a forced withdrawal, which lowers your taxable income, reduces the share of Social Security that gets taxed, and can keep you below IRMAA thresholds in your later years.
Can I reverse a Roth conversion if I change my mind?
No, you cannot reverse a Roth conversion. The IRS eliminated recharacterization of conversions under the Tax Cuts and Jobs Act, so once the calendar year closes, the amount you converted is final. This is exactly why sizing each conversion carefully matters; there is no undo button. Convert into the bracket you are comfortable paying and stop short of the next one.
Should I pay the tax on a conversion from the IRA or from other money?
You should pay the conversion tax from money outside the IRA, never from the IRA itself. Paying from outside lets the full converted amount land in the Roth and grow tax-free. Paying from inside shrinks the balance you were trying to protect, and before age 59½ the withheld amount counts as an early distribution subject to a 10% penalty on top of the tax.
How do Roth conversions affect my heirs?
Roth conversions leave heirs a tax-free account instead of a pre-tax one carrying a built-in tax bill. Under the SECURE Act 10-year rule, most non-spouse beneficiaries must empty an inherited IRA within ten years. Draining a pre-tax account on that timeline can hit your children during their peak earning years; a Roth lets them withdraw the same balance with no tax due at all.
When during the year should I actually do the conversion?
The best time to execute a conversion is in the fourth quarter, once your year's income is largely known. Converting in October through December lets you fine-tune the exact amount to fill your target bracket without guessing. A January conversion forces you to estimate income you have not yet earned, which risks overshooting a bracket or an IRMAA threshold you could have avoided with a few months' patience.
Ready to Map Your Gap Years?
The gap years are a window that closes on a fixed schedule, and the difference between using them on purpose and letting them pass is often six figures of lifetime tax. If this guide was useful, our deeper resource on the pre-RMD window walks through the year-by-year planning math for your specific situation. Download it at chesapeakefp.com and start building your own roth conversion strategy before the next window closes.
Want to go deeper? Our Roth Conversion Window walks through this step by step.
Disclosures
The information provided is for educational purposes only and should not be construed as investment advice. Investment strategies should be tailored to individual circumstances, risk tolerance, and goals. Past performance doesn't guarantee future results. Consult with qualified financial professionals regarding your specific situation.
Traditional IRA account owners have considerations to make before performing a Roth IRA conversion. These primarily include income tax consequences on the converted amount in the year of conversion, withdrawal limitations from a Roth IRA, and income limitations for future contributions to a Roth IRA. In addition, if you are required to take a required minimum distribution (RMD) in the year you convert, you must do so before converting to a Roth IRA.
A Roth IRA offers tax deferral on any earnings in the account. Qualified withdrawals of earnings from the account are tax-free. Withdrawals of earnings prior to age 59 ½ or prior to the account being opened for 5 years, whichever is later, may result in a 10% IRS penalty tax. Limitations and restrictions may apply.
Advisors associated with Chesapeake Financial Planners may be either (1) LPL Financial Registered Representatives offering securities through LPL Financial, Member FINRA and SIPC, and investment advisor representatives offering investment advice through Great Valley Advisor Group; or (2) solely investment advisor representatives offering investment advice through Great Valley Advisor Group and not affiliated with LPL Financial. Great Valley Advisor Group, and Chesapeake Financial Planners are separate entities from LPL Financial.
