Retirees Who Convert to a Roth in a Down-Market Year Move the Same Shares for Less Tax. Almost Nobody Times It.

Retirees Who Convert to a Roth in a Down-Market Year Move the Same Shares for Less Tax. Almost Nobody Times It.

David Beren

Sun, August 30, 2026 at 10:29 PM GMT+3 5 min read

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Quick Read

• Converting to a Roth during a market dip taxes shares at their depressed value, letting any rebound grow permanently tax-free inside the Roth.

• The 2017 Tax Cuts and Jobs Act eliminated recharacterization, making Roth conversions irreversible and raising the stakes of poorly timed moves.

• Larger conversions spike MAGI, potentially triggering Medicare IRMAA surcharges that jump from $203 to $284 monthly for joint filers crossing $218,000.

• Read More: Learn 7 ways to generate income with a $1,000,000+ portfolio (sponsor)

A Roth conversion moves money from a traditional IRA into a Roth IRA and treats the transferred amount as ordinary income in the year of the move. The tax bill is assessed on the dollar value converted, not on the share count. When account values are depressed, the same number of shares crosses the line at a lower taxable value, and every dollar of the eventual rebound accrues inside the tax-free account. That is the entire premise behind converting in a down-market year. Uptake is limited by behavior, cash flow, and a 2017 rule change that altered the maneuver's risk profile.

How the Mechanism Actually Works

The shares in a traditional IRA still represent the same fractional ownership of the same companies. What changes is the price tag the IRS uses to measure the conversion. A holding valued lower on the day of conversion produces a smaller addition to that year's taxable income, which means a smaller tax bill for the same slice of the portfolio. If those shares recover inside the Roth, the recovery is never taxed again. Required minimum distributions do not apply to Roth IRAs for the original owner, so the account can continue compounding untouched.

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The market context matters here. The S&P 500, tracked by the SPDR S&P 500 ETF Trust (NYSEARCA:SPY), is up 12.82% year-to-date through August 28, 2026, so calendar year 2026 is not a down year in aggregate. It did contain a real stress window: the VIX reached 31.05 on March 27, 2026, well into the high-fear zone, and sat above 25 on multiple sessions in March and early April. Retirees with a conversion plan on the shelf had a window. Most did not use it. The VIX is now 14.51, back in the low-volatility range, which is exactly when conversions look less appealing on the surface but cost more in taxes.

Caveat That Rewrote the Strategy

The Tax Cuts and Jobs Act of 2017 eliminated recharacterization, which was the ability to undo a Roth conversion by the following year's tax deadline. You can no longer reverse a conversion once it is done. So if you convert and the market takes a dive afterward, you end up paying tax on a value that is no longer sitting in the account, and there is no way to unwind the move. That is the whole risk of converting in a down market, and it is a risk that did not exist under the older rules many retirees still remember. The strategy is now a one-way door, which is why following a preset plan matters far more than trying to time the market bottom.

Why Almost Nobody Times It

Converting during a downturn means writing a tax check at the very moment your portfolio feels like it is shrinking and your confidence is shaken. Consumer sentiment sat at 55.2 in July 2026, below the 60 threshold that signals recessionary territory, after bottoming at 44.8 in May 2026. Acting against that kind of mood is psychologically tough. It also requires cash outside the IRA to cover the tax bill, because paying the tax from the converted balance defeats the purpose by shrinking what you actually recover inside the Roth. Converting in smaller chunks across the year sidesteps the timing problem. It accepts that nobody knows where the bottom is and spreads your taxable income across whatever prices the year delivers.

Bracket Room and Second-Order Effects

The 2026 brackets, set by IRS Revenue Procedure 2025-32, give retirees measurable room to convert at moderate rates. For married couples filing jointly, the 12% bracket runs up to $24,800, 22% applies over $100,800, and 24% applies over $211,400.

The standard deduction is $32,200 for joint filers and $16,100 for single filers in 2026. A retiree with modest ordinary income can often fill the 12% or 22% bracket with a conversion without pushing into higher rates.

A conversion raises modified adjusted gross income, or MAGI, which is the income figure Medicare uses to set surcharges. IRMAA, the income-related monthly adjustment amount, runs on a two-year lookback. A 2026 conversion feeds the 2028 premium. In 2026, Medicare Part B costs $202.90 per month with no surcharge for joint filers under $218,000 in MAGI, then jumps to $284.10 between $218,000 and $274,000, and $405.80 between $274,000 and $342,000.

Part D adds its own surcharge to the same brackets. Elevated MAGI can also increase the taxable share of Social Security benefits in the conversion year itself, a separate calculation that runs alongside the bracket check.

The 2027 Social Security COLA is currently tracking at 3.1%, so benefit income is rising into these thresholds rather than away from them. A decline offers a window to execute a plan already in place. With recharacterization gone since 2017, conversions cannot be unwound after the fact.

A $1,000,000 Income Portfolio

If you've saved over $1,000,000, this guide is for you. The last thing you want in retirement is to run out of money, you want your money to generate lasting income while you enjoy your life.

Now you can learn the strategies wealthy retirees use to fund their retirement with The Definitive Guide to Retirement Income from Fisher Investments. Download the guide today! (sponsor)

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