In the Three Years Between Her Last Paycheck and Her First Social Security Check, She Converted the Whole IRA. By the Time the Government Started Paying Her, There Was Nothing Left for It to Tax

If you have a traditional IRA and face years between your last paycheck and your first Social Security check, you own something almost nobody talks about: a window when your taxable income is whatever you decide to make it. No wages coming in. No benefits yet. Mandatory withdrawals still years away. Under SECURE 2.0, those mandatory withdrawals begin at age 73 for people born between 1951 and 1959, and at age 75 for those born in 1960 or later. During those three years in our illustrative retiree’s case, she used every inch of that space to run Roth conversions, and by the time the government started sending her benefit checks, very little was left in the pre-tax account to tax.

Almost no one recognizes the window while standing in it. Most people spend it worrying about spending. She spent it converting.

What Emptying the Pre-Tax Account Bought Her

Four things happened at once, and they compound. First, mandatory withdrawals disappeared from her future. A Roth IRA carries no required distributions during the owner’s lifetime, so she will never be forced to pull income she does not want in a year she did not choose.

Second, her Social Security largely stayed off the taxable line. The share of a benefit that becomes taxable depends on a measure called provisional income, which combines adjusted gross income, any tax-exempt interest, and half of the benefit itself. For a single filer, once that number exceeds $34,000, up to 85% of benefits can be taxed. For married couples filing jointly, the upper threshold is $44,000. Those thresholds have not moved since 1984. Traditional IRA withdrawals feed provisional income. Qualified Roth withdrawals do not. Once the pre-tax balance is gone, there is nothing left to drag the benefit into the taxable column.

Third, her Medicare premium is not being inflated later by her own withdrawals. The income-based surcharge on Medicare, known as IRMAA, is assessed on income from two years earlier. In 2026, the surcharge begins at $109,000 for single filers and $218,000 for married couples filing jointly, based on 2024 income. A retiree living on Roth dollars and Social Security is not feeding that lookback with taxable distributions. The bracket structure is a cliff, not a slope: one dollar over the threshold triggers the full surcharge for the entire year.

Fourth, the nature of what her heirs receive changes. They inherit dollars that have already been taxed, rather than a pre-tax account carrying its own distribution schedule and tax bill.

The Bill She Had to Pay

Compressing an entire IRA into three years almost certainly pushed her into higher rates in each of those years than a slower schedule would have. A more patient plan that filled only the cheap tax space each year would have kept her at lower rates for longer, and for many households that is the better answer.

The tax had to be paid from somewhere. Paying it out of the converted funds shrinks the pile that grows tax-free, which is why this strategy works far better for someone with outside savings to cover the bill. Conversions create a payment obligation during the year, not at filing, so large conversions require either estimated payments or withholding. Withholding from a retirement distribution is generally treated as paid evenly across the year, while estimated payments are credited when made, making withholding the simpler tool for most people.

If she bought health coverage through the marketplace before Medicare, a large conversion can erase premium assistance and make the true cost of the conversion far higher than the tax alone. The IRMAA lookback also means the big conversion years can raise her premiums in the first years of Medicare. The bill arrives after the strategy is finished, and it can come from two directions at once.

When This Move Fits and When It Backfires

Emptying the account tends to make sense for someone with a modest balance, outside cash to cover the tax, a long horizon, an expectation of higher rates later, or a strong wish to leave clean money to heirs. One wrinkle worth knowing: the One Big Beautiful Bill Act added a temporary $6,000 above-the-line deduction for taxpayers age 65 and older for tax years 2025 through 2028, up to $12,000 for a couple where both spouses qualify. That extra deduction widens the low-rate conversion room available in gap years before Medicare and Social Security take over, but it phases out for single filers above $75,000 in modified adjusted gross income and for joint filers above $150,000, so large conversions can erode or eliminate it.

The strategy tends not to make sense for someone with a very large balance where compression forces punishing rates, someone who will be in a lower bracket later anyway, someone charitably inclined who could move the money out tax-free through qualified charitable distributions, or someone who needs the cash to live on. For most households, the right answer is to fill the cheap space every year, not to drain the account.

Making the Window Longer

Delaying Social Security lengthens the gap and raises the eventual benefit. The claiming decision and the conversion plan are one decision, not two. Treat them separately and you leave conversion room on the table (we sized up those quiet years between the last paycheck and the first RMD in a free Roth window guide).

The Verdict

The window is real. It is short. It closes without an announcement. The goal is to use it deliberately, not to empty an account for its own sake. This is an illustration, not personalized advice.

Editor’s note: This update added the 2026 IRMAA surcharge thresholds ($109,000 single, $218,000 joint) and the cliff-bracket structure, specified the Social Security provisional income upper thresholds ($34,000 single, $44,000 joint) that determine when up to 85% of benefits become taxable, noted the SECURE 2.0 RMD starting ages of 73 and 75 depending on birth year, and added context on the One Big Beautiful Bill Act’s new $6,000 senior deduction (up to $12,000 per qualifying couple) and its phase-out for 2025 through 2028.

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