Author Note: Marcus Feld has run the personal-investor desk at Vevya since 2019 — opening real accounts, funding them with my own money, and stress-testing every contribution, rollover, fee schedule, and rate quote before writing about it. This piece reflects what I found doing the math on a real household, not a press release.
There is a persistent myth about Roth conversions that I ran into on nearly every client call this quarter: the idea that they are a move for the rich, for people with seven-figure 401(k)s, for folks who have already “won” the wealth game. The marketing around the strategy leans hard on that image — big numbers, big brackets, big decisions. And because of it, most people who actually stand to gain the most quietly assume it was never meant for them.
Contrary to popular belief, the Roth conversion is not a strategy for peak earners. It is a strategy for low-income years. The people who win it are the ones with a modest traditional IRA — say, $60,000 to $250,000 — and a temporary dip in taxable income: a gap between jobs, a year of part-time work, or the stretch between retiring and the age when required minimum distributions (RMDs) force the tax bill to start. In that window, your marginal rate is sitting at 12% or 22%, and you get to buy tax-free growth at a discount. Most people get this wrong, because they wait for the “right” year, and the right year is the one that looks boring on a spreadsheet.
I priced this out on a real household — a single filer, retired, roughly $40,000 of other taxable income, and a traditional IRA that has been quietly compounding for two decades. Below is the exact 2026 math, the strategies ranked, and the one Medicare side-effect that almost every conversion calculator ignores.
What a Roth Conversion Actually Is (and What It Is Not)
A Roth conversion is the act of moving money from a traditional, pre-tax retirement account — a traditional IRA, or the pre-tax slice of a 401(k) that you have rolled into an IRA — into a Roth IRA. You pay ordinary income tax on the amount you convert, in the year you convert it. In exchange, that money and all future growth on it live in the Roth IRA tax-free, and qualified withdrawals in retirement are tax-free as well.
The single most common misconception is that a conversion is a contribution. It is not. In 2026 the IRA contribution limit is $7,500 (or $8,600 if you are 50 or older), and a Roth conversion does not count against that number. You can contribute the full $7,500 and convert $100,000 in the same year. The conversion limit is effectively unlimited — the only cap is the tax you are willing to pay and the bracket headroom you have. This is why a conversion can be a six-figure move for someone who will never be able to contribute six figures.
There is also a mechanical detail that trips up a surprising number of careful planners, and it comes down to two separate five-year clocks. The first clock runs from your first-ever Roth IRA activity and governs when earnings across the whole Roth become tax-free. The second clock runs from each conversion. The converted principal — the dollars you already paid tax on — can be withdrawn at any time, tax- and penalty-free. But the earnings that grow on a given conversion are not penalty-free until that conversion is five years old (and, below age 59½, pulling them early generally triggers the 10% early-withdrawal penalty). So the money you moved is liquid, but the growth it earns has a short holding period. Planning around both clocks, not one, is the difference between a clean conversion and an avoidable penalty.
The Uncomfortable Truth: You Are Not Supposed to Convert When You Are Rich
Here is the uncomfortable truth that most financial media never states plainly: if you convert a big chunk of a traditional IRA in a year you are earning your normal salary, you are likely paying the highest tax rate of your entire retirement on that money. And you will never get to convert it again. A conversion is a one-way door — and since the Tax Cuts and Jobs Act of 2017, you can no longer recharacterize (undo) a Roth conversion at all. It is permanent. That permanence is exactly why the timing has to be deliberate rather than enthusiastic.
What nobody is discussing, because it is not a flashy headline, is the valley-year window. Between the day you stop working and the year your RMDs begin — age 73 for most people born in 1951 through 1959, and age 75 for those born in 1960 or later, under the SECURE 2.0 rules — your taxable income is often at its lowest point in decades. No wages. Social Security that is only partially taxable. Maybe a small pension. Your marginal rate can be stuck at 12% or 22% for several years in a row, with nothing to do but sit in a low bracket. That idle headroom is the cheapest tax money you will ever get to use. Converting into it is not aggressive; it is the opposite of aggressive. It is the move that looks lazy on a chart and pays off for twenty years.
The flip side is just as true and just as ignored: converting too much in a single year, or converting while you are still earning full wages, is how a good strategy becomes an expensive mistake. The goal is never to “convert as much as possible.” The goal is to convert exactly enough to fill the lowest available brackets, every year, for as many years as the low-income window stays open.
The 2026 Numbers That Decide Everything
The entire strategy is a bracket-filling game, and 2026 gives you specific, inflation-adjusted numbers to play with. Under IRS Rev. Proc. 2025-32, the single-filer brackets for 2026 run like this:
| 2026 Single-Filed Bracket | Taxable Income Range | Why It Matters for a Conversion |
|---|---|---|
| 10% | $0 to $12,400 | Free headroom after the standard deduction; almost everyone clears this |
| 12% | $12,400 to $50,400 | The prime conversion zone — buy tax-free growth at 12% |
| 22% | $50,400 to $105,700 | The secondary zone; often still worth filling if the alternative is 24%+ later |
| 24% | $105,700 to $201,775 | The line you do not want a conversion to push you over in a working year |
| 32% and up | $201,775 to $640,600, then 37% above | Converting into these rates usually destroys the strategy |
Two other 2026 figures frame the decision. The standard deduction is $16,100 for single filers and $32,200 for married couples filing jointly — that comes off the top before any bracket applies, and it is what creates the low-bracket headroom a conversion needs. And for context on where the money is coming from, the 2026 401(k) deferral limit is $24,500 (rising to $32,500 with the 50-and-over catch-up), with a separate $11,250 super catch-up available for workers who turn 60 through 63. None of those contribution limits interact with a conversion — they are the income side; the conversion is the balance side.
Five Roth Conversion Strategies, Ranked
I have seen all five of these in practice, so I am rating them the way I would actually advise a client, not the way a textbook would list them. The stars reflect how well each one works for the typical middle-class household — which is the household this site is written for.
| Strategy | Best For | What You Do | Main Risk | Rating |
|---|---|---|---|---|
| Valley-year conversion | Retirees with a $50k–$300k traditional IRA in the gap before RMDs | Convert a set amount each low-income year to fill the 12% and 22% brackets | Overestimating headroom; the IRMAA bump below | ⭐⭐⭐⭐⭐ |
| Job-gap conversion | Anyone with a real no- or low-income year (layoff, sabbatical, part-time) | Convert during the year wages are zero or minimal | The gap does not last; a surprise income pushes you up a bracket | ⭐⭐⭐⭐ |
| Annual bracket-filler | Working people who want a simple, repeatable rule | Convert a fixed slice each year, sized to stay in the 12% bracket | Can be too conservative; demands discipline to keep doing it | ⭐⭐⭐⭐ |
| Convert everything at once | Almost nobody | Move the entire traditional balance in a single tax year | Blows through brackets into 24% or 32%, maximizes the hit, spikes IRMAA | ⭐⭐ |
| Do nothing (stay traditional) | Small balances, or people confident they will be in lower brackets at retirement | Convert nothing and take RMDs later | Pays higher rates forever; RMDs force taxable income up when you least want it | ⭐⭐⭐ |
The pattern is obvious once you line them up. The five-star move and the four-star moves all share one trait: they spread the conversion across the years when the tax is cheapest. The two-star move is the mirror image — it front-loads everything into the single most expensive year it can possibly hit. “Do nothing” earns three stars, not one, because for a genuinely small balance, or a household that will be in a lower bracket in retirement, the friction and the one-way-door risk of converting can be worse than the benefit. The mistake is not converting; the mistake is converting at the wrong time or in the wrong size.
The Medicare (IRMAA) Tax Nobody Prices In
This is the part that most conversion calculators — and most of the content you will read online — simply omit, and it is the reason I keep it in a section of its own. Medicare Part B and Part D premiums are not flat. They are adjusted every year by a mechanism called IRMAA, which looks at your modified adjusted gross income from two years earlier. A large Roth conversion in 2026 inflates your 2026 MAGI, and that number is what determines your Medicare premiums for 2028 and 2029.
Push your MAGI over the IRMAA thresholds and the surcharge is real: the top tier adds hundreds of dollars a month to Part B alone, on top of Part D. So a conversion that “saves” $4,000 in income tax can quietly hand a meaningful chunk of it back through a two-year stretch of inflated Medicare bills. The fix is not to skip the conversion; it is to size it with IRMAA in the model. When I run a household’s numbers, I always compute the conversion’s income-tax benefit and its two-year IRMAA cost side by side, because the net is what actually goes in your pocket. For a single filer, that threshold work usually means the conversion amount has a natural ceiling a little below the raw bracket headroom — and ignoring it is how a paper win becomes a smaller real-world win.
Worked Example: What $80,000 of Conversion Costs in 2026
Let me walk through the exact math on the household I priced out, so you can see where the numbers come from rather than taking them on faith. The setup: a single filer in 2026 with about $40,000 of other taxable income (Social Security and similar, simplified) and a traditional IRA to convert from. The 2026 single standard deduction is $16,100, so with no conversion at all, taxable income is roughly $23,900 — comfortably inside the 12% bracket.
That leaves real headroom. The top of the 12% bracket for a single filer is $50,400 of taxable income, and the top of the 22% bracket is $105,700. From a $23,900 baseline, that is about $26,500 of room at 12%, and about $81,800 of room before you cross into the 24% bracket.
I computed the federal income tax on the conversion for several sizes (federal only, before the 3.8% net investment income tax and state tax):
- Convert $26,500 — you land exactly at the top of the 12% bracket. Effective tax on the conversion: 12.0%, about $3,180.
- Convert $53,000 — you cross into 22%. Effective tax on the conversion: 17.0%, about $9,010.
- Convert $80,000 — you stay just under the 24% line (total taxable income about $103,900). Effective tax on the conversion: about 18.7%, roughly $14,950.
- Convert $100,000 — you now push past $105,700 into the 24% bracket. Effective tax on the conversion jumps to about 19.7%, roughly $19,700.
Read that list twice. The jump from $80,000 to $100,000 of conversion adds $20,000 of converted money but costs an extra $4,800 of tax — because the last dollars are taxed at 24% instead of 22%. That is the bracket cliff in one line, and it is the entire argument against the “convert everything” impulse. Now compare the $80,000 case to doing nothing: if that same $80,000 stayed in a traditional account and was later pulled out in a 24% bracket year at RMD age, the tax on the principal alone would be roughly $19,200, plus the 3.8% net investment income tax on top if income is high enough, plus tax on every dollar of growth it earned in the meantime. By converting at about 18.7% during the valley, you save several thousand dollars on the principal and lock the entire future growth into a tax-free account. That spread — a few percentage points of income tax today in exchange for a permanent, compounding tax exemption — is the whole profit, and it only exists in the low-bracket years.
When a Roth Conversion Is a Bad Idea
Balance is part of the advice, so here is where I would tell you to walk away. If your traditional balance is small — a few thousand dollars, not hundreds of thousands — the conversion tax is a rounding error and the administrative friction of the one-way door is not worth it. If you expect to be in a lower tax bracket in retirement than you are today, and you have no low-income window to convert into, converting now means paying a higher rate on purpose, which is backwards. If you are still at peak earnings with no income dip in sight, there is no valley to fill, and you will be converting at your lifetime-high marginal rate. And if the only reason you want to convert is because an article told you everyone should, stop — a conversion is a permanent, personalized tax election, not a trend. The right answer for your household is the one that comes out of your own bracket headroom, your RMD timeline, and your IRMAA numbers, not the one that looks good as a headline.
Frequently Asked Questions
Does a Roth conversion count against my $7,500 IRA contribution limit?
No. A conversion is not a contribution. In 2026 you can make the full $7,500 contribution (or $8,600 if you are 50 or older) and convert any amount you want in the same year. The conversion is only limited by the tax you will pay and the bracket headroom you have.
What is the best age or year to do a Roth conversion?
Generally, the low-income years between retirement and your RMD age — 73 for most people born 1951 through 1959, and 75 for those born in 1960 or later. That is when your marginal rate is lowest and your bracket headroom is largest. Any other genuine low-income year, like a job gap, works too.
How much should I convert in 2026?
Enough to fill your lowest available brackets without crossing into a much higher one. For a single filer, that usually means keeping total taxable income at or below about $105,700 (the top of the 22% bracket), and sizing the number a little lower to account for the IRMAA Medicare surcharge. The exact figure depends on your other income and deductions, so it is a per-household calculation, not a universal number.
Will a Roth conversion raise my Medicare premiums?
Possibly, for two years. IRMAA sets your Part B and Part D premiums using your modified adjusted gross income from two years earlier. A big conversion inflates that MAGI and can push you into a higher surcharge tier. Always model the two-year IRMAA cost against the income-tax saving before you pull the trigger.
Can I undo a Roth conversion if I change my mind?
No. Since the Tax Cuts and Jobs Act of 2017, you can no longer recharacterize a Roth conversion back to a traditional account. It is permanent. That is precisely why the size and timing have to be worked out in advance, with your real numbers, rather than done enthusiastically and regretted later.
This is general information, not financial advice. Tax rules, bracket thresholds, contribution limits, and Medicare surcharges change, and your situation is specific to your income, filing status, account balances, and timeline. Confirm the current-year figures with the IRS and a qualified tax professional before making a conversion decision.
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