Can converting too much to a Roth backfire?

David KassirManaging Director of Manna Wealth Management

Retirement Planning

Can converting too much to a Roth backfire?

By David Kassir

Classical stone columns

Where oversized conversions go wrong

The question I hear from people in their seventies is whether they missed their chance once required minimum distributions start. They did not. The window gets narrower, but it does not close. The real question is how much to convert, and in which years.

The first trap is the bracket itself. Convert too much in a single year and the top slice of the conversion gets taxed at a rate you were trying to avoid. Sizing each year’s conversion with your current bracket in view keeps the tax bill proportional and leaves room to repeat the move next year.

The second trap is IRMAA, the income related surcharge on Medicare premiums. Crossing an IRMAA threshold can increase your monthly Medicare premiums, even when you exceed the threshold by only a small amount, and because Medicare looks back two years, the bill arrives long after the conversion that caused it. That is why we map a proposed conversion against the IRMAA tiers before touching anything, not after.

The third factor is your heirs. If your children are in higher brackets than you, converting at your rate to leave them tax free money can still win. If they are in lower brackets, it may be smarter to leave the IRA alone and let them inherit the tax bill at their cheaper rate. A conversion is a family tax decision, not just a personal one.

Further reading · Questions to discuss with your advisor about Roth conversions
  • How much can I convert this year without changing my tax bracket?
  • How would a conversion affect my Medicare premiums two years from now?
  • Are my heirs in higher or lower tax brackets than I am?
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Author: David Kassir, Managing Director of Manna Wealth Management

Last reviewed: October 26, 2026

Educational information, not individualized advice.

A worked example: the same conversion, two different sizes

This example is entirely hypothetical. The couple, the amounts, and the income figures are invented for illustration only. This is not a client story, not a real household, and not a result anyone achieved. It uses 2026 federal tax brackets and the 2026 Medicare premium table, both cited at the end of this section, so you can see exactly where the numbers come from.

Picture a married couple, both 73, filing jointly. Between Social Security, pensions, investment income, and their required minimum distributions, their modified adjusted gross income is $165,000 before any conversion. After the standard deduction, their taxable income is roughly $133,000. They are considering converting part of their traditional IRA to a Roth IRA.

Option one: a conversion sized to the bracket. They convert $50,000. Their taxable income rises to about $183,000, still inside the 22 percent bracket, which for joint filers in 2026 runs up to $211,400. The whole conversion is taxed at 22 percent, a federal tax bill of about $11,000 on the converted amount. Their modified adjusted gross income rises to $215,000, which stays under $218,000, the first Medicare IRMAA threshold for joint filers. Two years later, their Medicare premiums stay at the standard rate.

Option two: one oversized conversion. They convert $150,000 in a single year instead. Their taxable income rises to about $283,000. The slice of the conversion that lands above $211,400, roughly $71,000 of it, is taxed at 24 percent instead of 22 percent. That bracket creep alone adds roughly $1,400 of extra tax compared with taxing the whole amount at 22 percent, on top of a much larger bill due all at once. The quieter cost arrives later. Their modified adjusted gross income of $315,000 lands in the second IRMAA tier for joint filers, the band from $274,001 to $342,000 in the 2026 table. When Medicare looks back two years, each spouse’s monthly Part B premium is $405.80 instead of the standard $202.90. That is an extra $202.90 per person per month, about $4,870 over a year for the couple, plus an added surcharge on any Part D drug plan premium. One December decision, one premium bill two years later.

The alternative hiding in plain sight: converting the same $150,000 over three years, at $50,000 a year, could keep each year’s conversion inside the 22 percent bracket and under the first IRMAA threshold, assuming their other income stays similar. Nothing about the strategy changed. Only the sizing did.

Two cautions before anyone runs these numbers at home. First, the tax brackets and IRMAA thresholds are adjusted over time, and the year your own premium bill arrives will use that year’s table, not the 2026 table shown here. Second, this example ignores state taxes and every other individual detail. It shows the shape of the trade-off, not your answer.

References for this section

  • The amount converted from a traditional IRA to a Roth IRA is included in gross income in the year of the conversion, to the extent it would have been taxable as a distribution. See Internal Revenue Service, Publication 590-A, Contributions to Individual Retirement Arrangements (IRAs), and IRS Topic No. 309, Roth IRA Contributions: https://www.irs.gov/taxtopics/tc309
  • Required minimum distributions from traditional IRAs begin at age 73 for individuals born in 1951 through 1959, and at age 75 for those born in 1960 or later, under the SECURE 2.0 Act. Roth IRAs are not subject to required minimum distributions during the original owner’s lifetime. See Internal Revenue Service, Retirement Topics: Required Minimum Distributions (RMDs): https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-required-minimum-distributions-rmds and IRS Publication 590-B, Distributions from Individual Retirement Arrangements (IRAs): https://www.irs.gov/publications/p590b
  • 2026 federal income tax brackets, married filing jointly: the 22 percent bracket covers taxable income from $100,800 to $211,400, and the 24 percent bracket covers $211,400 to $403,550. Internal Revenue Service, Rev. Proc. 2025-32 (tax year 2026 inflation adjustments).
  • 2026 Medicare Part B premiums and IRMAA tiers: the standard monthly Part B premium is $202.90. For joint filers, the first surcharge tier begins above $218,000 of modified adjusted gross income, and the second tier, $274,001 to $342,000, carries a total monthly Part B premium of $405.80. Premiums are based on modified adjusted gross income from two years earlier. Centers for Medicare & Medicaid Services, “2026 Medicare Parts A & B Premiums and Deductibles,” fact sheet, November 14, 2025: https://www.cms.gov/newsroom/fact-sheets/2026-medicare-parts-b-premiums-deductibles

Educational information, not individualized advice.