Should You Keep Converting to Roth After Social Security and RMDs Begin?

Ross Marino |

For several years, a Roth conversion may have been a familiar part of your retirement plan. Now Social Security arrives regularly, required minimum distributions have begun, and the same conversion amount costs more. Those income sources may have started years apart, but together they have changed the comparison.

You do not have to keep converting to honor the earlier plan. You also do not have to stop simply because required withdrawals have arrived. The next conversion needs a current purpose and a price you are willing to pay.

What has changed about the next conversion?

Start with the income expected without a conversion: required withdrawals, pensions, investment income, and the taxable portion of Social Security. A conversion adds its taxable amount to that starting point. Previously untaxed IRA money generally becomes ordinary income in the conversion year; any after-tax basis requires proper calculation.[1]

You cannot convert your required minimum distribution, or RMD. Satisfy the applicable RMD before converting eligible remaining IRA assets, with account-specific sequencing confirmed by your tax professional and custodian. A conversion does not replace the required withdrawal.[1]

Additional income can also make more Social Security taxable, but that effect is not automatic. If the maximum taxable share is already included, a conversion does not make still more of the benefit taxable. The federal ceiling is 85% of benefits, not an 85% tax rate.[2]

What belongs in the current price?

Compare the household’s total cost with and without the proposed conversion. Include federal and state taxes, income-sensitive deductions, and Medicare. Higher modified adjusted gross income can raise Part B and Part D premiums through income-related adjustments, generally using the tax return from two years earlier. A conversion can therefore affect a later premium year; if both spouses are enrolled, examine each person’s premiums.[3]

Money used to pay conversion tax also has a job. Will paying it leave comfortable resources for spending, care, and unexpected expenses? If you must sell appreciated investments to raise that cash, include the resulting tax. Conversion research shows why the tax-payment source and time before the money is used can materially change the comparison.[4]

What would more Roth money actually do for you?

Name the future choice you want to preserve. Qualified Roth withdrawals can provide spending money without adding federal taxable income. Holding accounts with different tax treatment may help you respond to uncertain future tax circumstances; research supports evaluating that flexibility without treating it as a reason to convert every available dollar.[5]

For a couple, the purpose may involve a surviving spouse. A joint return may generally be available for the year of death, while later filing status depends on eligibility; many retirees eventually file as single taxpayers.[6] Compare the survivor’s likely income, spending, and taxes together. A higher marginal rate alone does not establish a harmful dollar outcome or prove that a conversion helps.[7]

An intentional legacy goal may also justify review, but the intended beneficiaries and estate arrangements matter. Research on conversion value highlights uncertainty in future tax rates and the timing of benefits. A reason to own Roth assets does not establish that this year’s conversion price is attractive.[8]

Dovetail Principle: When Life Changes, the Plan Can Change Without Starting Over

Your earlier conversions may still matter even though your income has changed. Keep that purpose visible as you reconsider the amount and timing. Adjusting the strategy can preserve the plan’s intent without repeating last year’s transaction.

How can you adapt the strategy deliberately?

Use these states to connect the purpose, price, and reason for revisiting the decision. They are alternatives, not a ranking.

Continue

Purpose still served

Additional Roth flexibility still serves a defined household goal.

Current cost to examine

The proposed amount’s full tax, premium, and cash cost.

What would change the decision

A weaker future benefit or a higher current cost.

Reduce

Purpose still served

Some additional Roth money still serves the goal.

Current cost to examine

Whether later conversion dollars cost more than earlier ones.

What would change the decision

Higher cost calls for a pause; lower cost may support more.

Pause

Purpose still served

The goal remains, but no conversion is justified now.

Current cost to examine

The value of retaining tax-payment money for present needs.

What would change the decision

Lower future cost, clearer facts, or a changed household goal.

Have your financial planner and tax professional compare no conversion with smaller and larger amounts using updated projections, including Medicare consequences. Bring an estate attorney into beneficiary or trust questions. Test plausible future circumstances rather than relying on guaranteed lifetime savings.

If the original purpose has disappeared or existing Roth assets already meet it, ending conversions may be appropriate. Otherwise, retain the strategy only to the extent its purpose justifies the additional current cost. A smaller conversion or a deliberate pause can keep the plan working for the life you are living now.

Related Reading: If a conversion still fits, continue with How Should You Coordinate Required Minimum Distributions and Roth Conversions in the Same Year? for the required-withdrawal and conversion sequence.

About the author

Ross Marino, CFP®, CeFT®, is the Founder & CEO of Dovetail Financial and creator of Human-First Financial Guidance®. He helps people nearing or living in retirement connect their lives and wealth so that financial decisions become clearer, more personal, and easier to navigate.

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Notes

  1. Publication 590-A (2025), Contributions to Individual Retirement Arrangements (IRAs), conversion and required-distribution rules, Internal Revenue Service.
  2. How is Social Security taxed?, AARP, updated December 12, 2025.
  3. Medicare Premiums, Social Security Administration.
  4. The Arithmetic of Roth Conversions, Edward F. McQuarrie and James A. DiLellio, Journal of Financial Planning, May 2023.
  5. Tax uncertainty and retirement savings diversification, David C. Brown, Scott Cederburg, and Michael S. O’Doherty, Journal of Financial Economics, 2017; University of Arizona research record.
  6. Publication 501 (2025), Dependents, Standard Deduction, and Filing Information, surviving-spouse filing rules, Internal Revenue Service.
  7. Widow Tax Hit Debunked, Edward F. McQuarrie, Journal of Financial Planning, December 2023.
  8. Net Present Value Analysis of Roth Conversions, Edward F. McQuarrie, Journal of Financial Planning, September 2024.

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