The Roth Conversion Window: When It Makes Sense for Pre-Retirees
For many pre-retirees, the years between leaving a full-time career and the start of Required Minimum Distributions at age 73 are the most favorable tax window they will ever have for Roth conversions. Income is temporarily low, brackets are more forgiving, and the decisions made here can compound quietly for decades. But sizing those conversions correctly, without triggering IRMAA surcharges or bracket creep, requires your financial plan and your tax picture to work together, not in parallel.
In this article
Why the Conversion Window Matters
For decades of your working career, a Roth IRA may have been out of reach. High earned income pushed you above the contribution limits, and the tax deduction from a traditional 401(k) or IRA was too valuable to give up. So you did the right thing: you saved in pre-tax accounts and let those funds compound for years.
Now the calculus is changing. You are within five to ten years of retirement, or perhaps you have already left your primary career. Your earned income has dropped. Social Security has not started. Required Minimum Distributions are still years away. And your traditional IRA or 401(k) has grown substantially.
This is the Roth conversion window: the years when your taxable income is temporarily low, giving you an opportunity to move money from pre-tax accounts into a Roth IRA at a lower marginal tax rate than you faced during your peak earning years, and likely lower than the rates that will apply when RMDs force large mandatory distributions in your 70s and 80s.
Used strategically, this window can permanently reduce your lifetime tax burden, lower Medicare premiums, and leave your heirs a more tax-efficient inheritance. Missed entirely, it closes quietly and you cannot recover it.
What a Roth Conversion Actually Is
A Roth conversion is straightforward in mechanics: you move funds from a traditional IRA (or roll over a pre-tax 401(k) into a traditional IRA first, then convert) into a Roth IRA. The converted amount is included in your gross income for the year as ordinary income and taxed at your marginal rate. In exchange, those funds now sit in a Roth IRA where they grow tax-free and are never subject to RMDs during your lifetime.
There is no income limit for conversions. Anyone with a traditional IRA can execute a traditional IRA to Roth conversion, regardless of income. This is sometimes called the “backdoor Roth” strategy when used by high earners who cannot contribute directly, but for pre-retirees in the conversion window, it is simply a direct transfer executed with your IRA custodian.
Traditional IRA vs. Roth IRA: Key Differences at a Glance
Before modeling whether a conversion makes sense for your situation, it helps to see the two account types side by side. The table below summarizes the core tax treatment differences that drive the Roth conversion decision.
| Feature | Traditional IRA / 401(k) | Roth IRA |
|---|---|---|
| Contributions | Pre-tax (reduces taxable income in the contribution year, subject to income and participation rules) | After-tax (no deduction; income limits apply for direct contributions, but there is no limit for conversions) |
| Growth | Tax-deferred (no tax on dividends, interest, or gains while inside the account) | Tax-free (qualified earnings grow and are withdrawn free of federal income tax) |
| Withdrawals in Retirement | Fully taxable as ordinary income at your marginal rate in the year of withdrawal | Tax-free for qualified distributions (account open ≥5 tax years; owner age 59½ or older) |
| Required Minimum Distributions (RMDs) | Required beginning at age 73 (under current law), whether you need the income or not; RMDs are taxable | No RMDs during the original owner’s lifetime; assets can grow tax-free indefinitely or be passed to heirs |
| Estate / Inheritance | Heirs pay ordinary income tax on inherited distributions (10-year rule for most non-spouse beneficiaries under SECURE 2.0) | Heirs generally receive distributions income-tax-free (10-year rule applies, but the distributions themselves are not taxable) |
| IRMAA / Medicare Impact | Withdrawals count toward MAGI, which drives Medicare Part B and D premium surcharges | Qualified withdrawals do not count toward MAGI, so they do not increase Medicare premium surcharges |
Evaluating Whether a Roth Conversion Makes Sense
The Roth conversion decision is not a one-size-fits-all rule of thumb. It is a calculation that requires looking at your actual situation across multiple dimensions.
Current vs. Expected Future Tax Brackets
The core question in any Roth conversion tax bracket analysis is: are you in a lower bracket today than you expect to be when you start taking distributions?
For many pre-retirees, the answer is yes, but the magnitude matters. If you are currently in the 22% federal bracket and project that RMDs plus Social Security will push you into the 24% or 28% bracket in your mid-70s, a conversion at 22% today creates a permanent saving on every converted dollar. If your future bracket will be roughly the same as today, the benefit is less clear-cut, though Roth accounts still offer estate planning and RMD flexibility advantages.
A thorough analysis models:
- Your projected RMDs at ages 73, 75, and 80 based on current account balances and realistic growth assumptions.
- Social Security income and at what income levels your benefits become taxable (up to 85% of benefits can be taxable once your “combined income” exceeds IRS thresholds). How your Social Security claiming age fits into this picture matters too; see our Social Security claiming strategy guide for a closer look.
- Any pension or part-time income that will continue into retirement.
- Your available bracket space today: how much additional taxable income can you recognize before crossing into the next federal bracket?
Getting these projections right requires actual tax-return-level modeling: not a quick calculator estimate. The difference between $80,000 and $100,000 in Roth conversions in a given year can mean the difference between staying in the 22% bracket and tripping into the 24% bracket, or crossing an IRMAA tier that costs thousands in Medicare premiums two years later.
2026 Federal Tax Brackets: How Much Conversion Room Do You Have?
Knowing exactly where your current bracket ends is the starting point for sizing a conversion. Under the rates that apply for the 2026 tax year, following the One, Big, Beautiful Bill Act’s extension of the current rate structure, the federal brackets are as follows.
| Marginal Rate | Single Filers | Married Filing Jointly |
|---|---|---|
| 10% | $0 to $12,400 | $0 to $24,800 |
| 12% | $12,401 to $50,400 | $24,801 to $100,800 |
| 22% | $50,401 to $105,700 | $100,801 to $211,400 |
| 24% | $105,701 to $201,775 | $211,401 to $403,550 |
| 32% | $201,776 to $256,225 | $403,551 to $512,450 |
| 35% | $256,226 to $640,600 | $512,451 to $768,700 |
| 37% | Over $640,600 | Over $768,700 |
The 2026 standard deduction is $16,100 for single filers and $32,200 for married couples filing jointly, per the same IRS guidance, so the first dollars of income convert without any federal tax at all before a bracket even applies. Knowing these breakpoints to the dollar, alongside your other projected income for the year, is what allows a conversion to be sized precisely rather than estimated.
Tax-Bracket Arbitrage: A Worked Example
The term “bracket arbitrage” simply describes converting a dollar of pre-tax savings today at a lower marginal rate than the rate that dollar would likely face if left in the IRA until RMDs begin. The size of that spread, not just its existence, is what determines whether a conversion is worthwhile.
The following is a hypothetical example for illustration only and does not represent any specific client or outcome. Consider a married couple with $60,000 of other taxable income in a given year. Using the 2026 MFJ brackets above, they have room to convert up to $151,400 (the gap between $60,000 and the top of the 22% bracket at $211,400) before crossing into the 24% bracket. The table below compares the hypothetical tax cost of converting that $150,000 today against withdrawing the same $150,000 later at two different projected future rates.
| Scenario | Amount (Illus.) | Marginal Rate Applied | Approx. Tax Cost (Illus.) |
|---|---|---|---|
| Convert now, in the 22% bracket | $150,000 | 22% | $33,000 |
| Withdraw later, if RMDs and Social Security push income into the 24% bracket | $150,000 | 24% | $36,000 ($3,000 more) |
| Withdraw later, if income instead reaches the 32% bracket | $150,000 | 32% | $48,000 ($15,000 more) |
The wider the projected spread between your bracket today and your bracket later, the more a conversion accomplishes. When the spread is narrow (for example, staying in the 22% bracket either way), a conversion still offers RMD reduction and estate planning value, but the pure tax-rate arbitrage is smaller and the decision depends more on the other dimensions covered below.
RMD Planning: Modeling the Distributions Conversions Are Designed to Reduce
A Roth conversion is, in large part, a bet on reducing the size of mandatory distributions you will not be able to avoid later. Required Minimum Distributions are calculated by dividing your prior year-end traditional account balance by a life expectancy factor from the IRS Uniform Lifetime Table. A larger account balance at age 73 means a larger mandatory distribution, whether or not you need the income that year.
| Age | Life Expectancy Factor | Approx. % of Balance Withdrawn |
|---|---|---|
| 73 | 26.5 | 3.8% |
| 75 | 24.6 | 4.1% |
| 78 | 22.0 | 4.5% |
| 80 | 20.2 | 5.0% |
Hypothetical example, for illustration only: a $1,850,000 traditional IRA at age 73 with no prior conversions produces an RMD of roughly $69,800 (dividing by the age-73 factor of 26.5). If, instead, that same account holder had spent seven years converting a portion of the balance during the conversion window, leaving a projected $1,150,000 in the traditional IRA by age 73, the RMD on the smaller balance would be roughly $43,400. That is approximately $26,400 less mandatory taxable income in that single year, which in turn affects the bracket the RMD lands in, how much of Social Security becomes taxable, and whether an IRMAA tier is triggered. The effect compounds every year RMDs continue. These figures are illustrative only and do not reflect any specific account or client.
IRMAA: The Medicare Premium Surcharge Cliffs
One of the most important, and most commonly overlooked, dimensions of Roth conversion strategy planning is Medicare’s Income-Related Monthly Adjustment Amount, or IRMAA. Under IRMAA, your Medicare Part B and Part D premiums are not flat rates. They increase in steps based on your Modified Adjusted Gross Income (MAGI) from two years prior.
The mechanics matter: income you recognize during your conversion window directly affects your Medicare premiums two years later. Aggressive conversions in your late 60s can trigger IRMAA surcharges in your early 70s, adding thousands of dollars per year in healthcare costs. For a married couple, the combined impact can exceed $7,000 annually at higher income tiers.
The stair-step structure means precision is critical. Recognizing just $1 above an IRMAA threshold triggers the full surcharge for that tier. A conversion analysis that does not explicitly model IRMAA thresholds is incomplete.
Net Investment Income Tax (NIIT) Thresholds
If your MAGI exceeds $200,000 (single) or $250,000 (married filing jointly), net investment income (interest, dividends, and capital gains) is subject to an additional 3.8% Net Investment Income Tax. Roth conversions increase your MAGI, which can pull otherwise below-threshold investment income into NIIT exposure. For pre-retirees with substantial taxable brokerage income, this interaction deserves explicit modeling.
Market Timing: Converting When Account Values Are Temporarily Down
The tax owed on a conversion is based on the dollar value moved into the Roth, not on what that value does afterward. That mechanical fact creates an opportunity worth understanding, separate from any attempt to predict where markets are headed. If your traditional IRA is temporarily down in value, for example after a market pullback, converting the same target dollar amount moves more shares or units into the Roth for the same tax bill. If those holdings later recover, that recovery happens inside the Roth and is never taxed again. If they do not recover on the timeline you expected, the conversion still accomplished its purpose of reducing the traditional IRA balance and the RMDs tied to it; the tax cost simply reflected the account’s value on that particular day.
This is a reason some pre-retirees choose to accelerate a planned conversion during a down period within their multi-year schedule, not a reason to guess at market direction or delay conversions while waiting for a decline. A conversion plan built around your tax brackets and income projections should be the anchor; opportunistic timing within that plan is a secondary refinement, not the primary strategy.
Partial vs. Full Conversions: Two Different Decisions
Converting an entire traditional IRA balance in a single year is possible, but for most pre-retirees with substantial balances, it is not the right approach. A full conversion recognizes the entire balance as income in one year, which typically pushes a large portion of it through the higher brackets, triggers the top IRMAA tiers for at least one Medicare cycle, and may waste the lower-bracket space available in future years of the conversion window. A partial, laddered conversion spreads the same total amount across several years, filling only the target bracket each year.
| Dimension | Full, Single-Year Conversion | Partial, Multi-Year Conversion |
|---|---|---|
| Tax bill timing | One large bill due in a single tax year | Smaller bills spread across several years |
| Bracket impact | Likely to cross into higher brackets on a large portion of the balance | Can be sized each year to stay within a target bracket |
| IRMAA exposure | High: a single-year MAGI spike can cross multiple surcharge tiers | Lower: annual sizing can be modeled to manage MAGI relative to thresholds |
| RMD elimination | Immediate and complete for the converted account | Gradual, phased in over the length of the conversion window |
| Planning complexity | Lower: one transaction, but a materially higher upfront tax cost | Higher: requires annual income modeling coordinated with your tax return |
For most pre-retirees with meaningful traditional IRA balances, a partial approach sized to available bracket space each year produces a better outcome than either doing nothing or converting everything at once. A full conversion can occasionally make sense for a smaller account balance, or for an account holder with an unusually short time horizon before RMDs begin and limited concern about a single high-income year, but that determination should follow a full projection rather than a general rule.
The Five-Year Rules: Two Different Clocks
Roth IRAs are governed by two separate five-year rules, and the conversion window is exactly when the distinction matters most. The first is the rule on earnings: to withdraw earnings tax-free, your first Roth IRA must have been open for at least five tax years and you must be age 59½ or older. The second is the rule on each individual conversion: the converted principal from each conversion must remain in the Roth for five years before it can be withdrawn without a 10% penalty, unless you are already 59½ or older, in which case this second rule generally does not apply to you.
For most pre-retirees in the conversion window who are past 59½, the conversion-specific five-year clock is not a practical obstacle since the penalty exception already applies. The earnings clock is the one to watch if you are opening your very first Roth IRA as part of this strategy: it starts on January 1 of the year of your first contribution or conversion, so opening that account earlier in the window, even with a modest initial conversion, starts the clock sooner rather than later.
New York State Tax Considerations
For our clients on Long Island, in Manhattan, and throughout the New York metro area: New York State taxes Roth conversions as ordinary income at state rates. New York’s top rate of 10.9% (for high earners) means a conversion that looks cost-effective at the federal level may be more expensive in total when state taxes are included. Conversely, if you plan to relocate to a no-income-tax state in retirement, converting before you move can eliminate the state tax entirely, a significant planning opportunity worth evaluating carefully.
Common Roth Conversion Mistakes
The conversion window is an opportunity, but it is possible to execute it poorly. Here are the most common mistakes we see:
Converting Too Much in One Year
The most frequent error is converting too aggressively in a single year without modeling the full tax impact. A large conversion can:
- Push you from the 22% to the 24% (or higher) federal bracket, reducing the tax efficiency of the conversion.
- Trigger an IRMAA tier that raises your Medicare premiums for the following two years.
- Cause more of your Social Security benefits to become taxable.
- Subject more of your investment income to the 3.8% NIIT.
The optimal approach is usually to spread conversions across multiple years, filling your current bracket carefully each year rather than attempting a large one-time conversion.
Paying the Tax Bill From Inside the IRA
If you withhold funds from the IRA itself to cover the conversion tax, you reduce the amount that actually lands in the Roth, and you lose the long-term compounding benefit of those withheld dollars growing tax-free. The optimal approach is to pay the conversion tax from a taxable brokerage account or other non-retirement savings, so the full converted amount moves into the Roth. If you are under age 59½, withholding from the IRA to pay the tax can also trigger a 10% penalty on the withheld portion.
Ignoring the Five-Year Rule
Roth IRAs have two five-year rules, and confusing them is a common source of errors. Each conversion begins its own five-year clock for penalty-free access to that specific converted amount (for those under 59½). The separate five-year rule on Roth IRA earnings requires the account to have been open at least five tax years before earnings can be withdrawn tax-free. For most pre-retirees converting in their 60s, the penalty issue is less pressing, but if you are opening a Roth IRA for the first time as part of this strategy, the earnings five-year clock starts now and is worth factoring into your planning timeline.
Converting Without a Multi-Year Plan
A Roth conversion executed without a multi-year projection is guesswork. Whether conversions make sense, and how much to convert each year, depends on your full income picture: expected Social Security timing, projected RMD amounts, capital gains harvesting plans, charitable giving, and future tax law expectations. Executing conversions year by year without a coordinated roadmap often results in suboptimal bracket and IRMAA outcomes that could have been avoided.
What a Multi-Year Roth Conversion Ladder Might Look Like
One of the most effective ways to use the conversion window is to spread conversions across several years, carefully filling up a lower tax bracket each year rather than converting a large lump sum all at once. The table below shows a hypothetical illustration of how this might work for a married couple filing jointly who retire at 63 with a $1.2 million traditional IRA, modest other income, and Social Security beginning at 70.
Important: The numbers below are entirely hypothetical and for illustration only. They are not a projection or guarantee of results, and they do not reflect any specific client situation. Federal bracket boundaries, IRMAA thresholds, and tax rates are subject to change. Individual circumstances vary significantly. This is not personalized tax or financial advice.
| Year / Age | Other Taxable Income (Illus.) | Roth Conversion Amount (Illus.) | Approx. Top Bracket Used | Key Consideration |
|---|---|---|---|---|
| Year 1, Age 63 | $40,000 (part-time / dividends) | $50,000 | 22% federal | First year of conversion window; fill lower portion of 22% bracket. Pay tax from taxable savings, not IRA. |
| Year 2, Age 64 | $35,000 (investment income) | $55,000 | 22% federal | Slightly larger conversion; confirm IRMAA MAGI stays below first threshold (~$206,000 MFJ for 2024). Two-year lookback means 2024 income affects 2026 Medicare premiums. |
| Year 3, Age 65 | $35,000 (investment income) | $55,000 | 22% federal | Medicare begins at 65; IRMAA exposure is now active. This year’s MAGI (2027) affects 2029 Medicare premiums. Careful sizing required. |
| Years 4–6, Ages 66–68 | $30,000–$35,000 | $50,000–$60,000 per year | 22%–24% federal | Conversions continue annually. Total MAGI (other income + conversion) is modeled to stay below IRMAA Tier 1 each year. Conversion amount may vary based on that year’s actual income. |
| Year 7, Age 69 | $30,000 | $45,000 | 22% federal | Approaching Social Security start (age 70). Modeling confirms that once SS begins (~$40,000/year taxable equivalent), the optimal conversion amount decreases significantly. Final full-bracket conversion year. |
| Age 70+: Social Security Begins | $40,000 SS (taxable portion) + investment income | Reduced or paused | Varies | Income rises meaningfully. Conversions may still occur in smaller amounts if bracket space remains, but the math is re-evaluated each year. |
| Age 73+: RMDs Begin | SS + RMD (potentially $60,000–$80,000+) | Likely minimal or none | 24%–32% (illustrative) | RMDs from the (now smaller) traditional IRA are mandatory and taxable. Because conversions reduced the traditional IRA balance over years 1–7, RMDs are lower than they would have been. This is the long-term benefit of the strategy. |
The illustrative outcome: by converting roughly $360,000–$380,000 over seven years (hypothetical), this couple moves a meaningful portion of their pre-tax savings into a Roth IRA at the 22% federal bracket, before Social Security and RMDs would push that income into higher brackets. The traditional IRA balance at age 73 is smaller, which means lower mandatory distributions, and potentially lower Medicare premiums, throughout their 70s and 80s. The specific numbers for any individual will differ substantially based on their actual income, balances, state taxes, and life circumstances.
Why Coordinated Planning and Tax Preparation Matter
Roth conversion analysis is one of the clearest illustrations of why financial planning and tax preparation work best when they happen under the same roof.
A conversion decision is not simply a financial planning question (“does the math work over 20 years?”). It is also a tax preparation question that requires knowing your current-year AGI, your itemized vs. standard deduction, your capital gains, your MAGI relative to IRMAA thresholds, and your state income tax position, all simultaneously. Without the actual tax picture in front of them, a financial planner is estimating. Without the long-term projection, a tax preparer is optimizing only for this year.
At United Financial Planning Group, our team of CFP® professionals, CPAs, and Enrolled Agents approaches Roth conversion analysis exactly this way. We are not relying on a generic planning calculator. We build multi-year conversion models using tax-return-level detail: your specific account balances, projected growth rates, expected income sources, IRMAA thresholds, NIIT exposure, and New York State tax impact, all modeled together so we can identify the optimal conversion amount for each year of the window.
Because our advisors work alongside our tax professionals, there are no “surprises” at tax time. The conversion amounts we plan in the spring are coordinated with your tax return in the winter. Adjustments can be made in real time as your income picture changes, something that is simply not possible when your financial planner and your accountant are in separate firms that communicate once a year, if at all.
We are fee-only and fiduciary: we have no financial incentive to recommend a Roth conversion (or any other strategy) except that it is in your best interest. No commissions, ever.
Is This the Right Time for You?
The conversion window is time-limited by definition. Once RMDs begin at age 73, your annual taxable income rises mechanically and the conversion math changes. Once Social Security starts, your combined income pushes higher. Every year of inaction narrows the window.
The question is not whether Roth conversions are theoretically valuable, and for most pre-retirees with substantial traditional IRA balances, they are. The question is how much to convert, in which years, and how to coordinate it with the rest of your income, tax, and investment picture. That is where the real planning work happens.
If you are within five to ten years of retirement, or have already stopped working, this is the right time to have that analysis done properly. Learn more about our approach to tax planning and retirement planning, or reach out directly.
Schedule a Personalized Roth Conversion Analysis
We invite you to schedule a complimentary conversation with our team at United Financial Planning Group. We serve clients in Hauppauge, Manhattan, Lake Success, and throughout New York, as well as clients nationwide who value the integrated planning approach.
In this conversation, we will review your current account structure, model your projected RMDs and Social Security income, identify your available conversion window, and assess whether a multi-year Roth conversion strategy fits your situation. There is no pressure and no obligation: just a clear-eyed look at whether this strategy makes sense for you.
Contact United Financial Planning Group to schedule your complimentary analysis. The window may be open longer than you think, but it will not stay open forever.
Disclosures
This article is provided for general educational and informational purposes only and does not constitute personalized financial, tax, investment, or legal advice. Roth conversion analysis involves complex variables specific to each individual’s income, tax bracket, account balances, state of residence, and long-term financial goals. Tax laws, Medicare premium schedules, IRMAA thresholds, and RMD rules are subject to change. The examples and scenarios described are for illustrative purposes only and should not be relied upon as a projection or guarantee of results. Please consult a qualified financial advisor and tax professional regarding your specific circumstances before making any decisions.
Frequently Asked Questions
- What is a Roth conversion and how does it work?
- A Roth conversion is the process of moving money from a traditional IRA (or other pre-tax retirement account) into a Roth IRA. The converted amount is added to your taxable income in the year of conversion and taxed at your ordinary income rate. In exchange, the funds now grow tax-free inside the Roth IRA and are not subject to Required Minimum Distributions (RMDs) during the account owner’s lifetime. Qualified withdrawals in retirement are completely tax-free.
- What is the Roth conversion window for pre-retirees?
- The “conversion window” refers to the period between retirement (or a significant reduction in earned income) and the time when Required Minimum Distributions begin at age 73 and Social Security benefits start. During this window, many pre-retirees are in a lower tax bracket than they were during their peak earning years and lower than they expect to be when RMDs force large taxable distributions later. This temporary low-income period creates an opportunity to convert traditional IRA funds to Roth at a relatively favorable tax rate.
- What is IRMAA and how does it affect Roth conversion planning?
- IRMAA stands for Income-Related Monthly Adjustment Amount. It is a surcharge added to Medicare Part B and Part D premiums for beneficiaries whose Modified Adjusted Gross Income (MAGI) exceeds certain thresholds. Because IRMAA is based on income from two years prior (for example, your 2024 income affects your 2026 Medicare premiums), a Roth conversion that pushes MAGI above an IRMAA tier can increase Medicare costs significantly. The surcharges are structured as stair-steps, meaning a small excess over a threshold can trigger thousands of dollars in additional annual premiums. This must be carefully modeled when sizing annual conversions.
- What is the Roth five-year rule?
- There are actually two five-year rules for Roth IRAs. The first applies to the earnings inside a Roth: to take qualified, tax-free withdrawals of earnings, the account must have been open for at least five tax years and the owner must be age 59½ or older. The second applies to each individual Roth conversion: converted funds must remain in the Roth for five years before withdrawal to avoid the 10% early withdrawal penalty (if the account owner is under 59½). For most pre-retirees over age 59½, the five-year penalty rule on conversions is less of a concern, but the earnings rule still matters if you are opening a new Roth IRA for the first time.
- Should I pay Roth conversion taxes from my IRA or from outside funds?
- In most cases, paying the conversion tax from outside the IRA (using funds in a taxable brokerage account, savings, or other non-retirement assets) is more advantageous. When you pay the tax from outside the IRA, the full converted amount moves into the Roth, maximizing the tax-free growth. If you withhold from the IRA itself to cover the tax, you effectively convert a smaller amount and lose the benefit of that withheld portion growing tax-free. In addition, if you are under age 59½, withholding from the IRA may trigger a 10% early withdrawal penalty on the withheld portion.
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