Jeremy Keil examines how tax law changes might affect Roth conversion strategies for retirees in 2026.

A few years ago, Roth conversions felt like one of those rare financial strategies that was almost too obvious to ignore. Taxes were historically low. The Tax Cuts and Jobs Act had put a clear expiration date on those lower brackets. And for many retirees, the logic seemed airtight: pay taxes now at a lower rate so you don’t pay more later.

Fast forward to today, and that certainty just isn’t the same.

With new tax legislation making today’s lower tax brackets permanent—at least for now—many retirees are asking a very different question: Are Roth conversions still worth it in 2026 and beyond?

The short answer is yes. But not for the reasons many people think.

The real problem isn’t Roth conversions themselves. The problem is the assumptions people make about them.

Roth conversions exploded in popularity when it appeared obvious that taxes were about to rise. The assumption was straightforward: convert while rates are low, avoid higher taxes later, and you’ll come out ahead.

But that assumption rested on two ideas that don’t always hold up:

That tax rates would definitely rise.
That income in retirement would naturally fall.

For some people, both are true. For many others, neither is.

Markets have been strong. Retirement accounts are larger than expected. Capital gains, pensions, and Social Security stack on top of one another. And suddenly, retirement income isn’t as “low tax” as it once looked on paper.

The Difference Between Tax Bracket and Tax Cost

One of the most common mistakes retirees make is focusing on their tax bracket instead of their tax cost.

On a tax return, you might see yourself in the 12% or 22% bracket and assume Roth conversions are inexpensive. But once Social Security enters the picture, the math becomes more complicated.

As additional income comes in, Social Security benefits that were once tax-free begin to become taxable—up to 85% of the benefit. In that phase-in range, every dollar withdrawn from a traditional IRA can cause more Social Security to be taxed. The result is an effective tax cost that can be significantly higher than the bracket suggests.

This is where many well-intentioned Roth strategies quietly go off track.

Medicare Premiums Change the Equation

Taxes aren’t the only cost that matters.

Medicare income-related premium adjustments—often called IRMAA—are triggered when income crosses certain thresholds. These surcharges commonly appear in two situations: when required minimum distributions begin, and when one spouse passes away and income thresholds are suddenly cut in half.

A Roth conversion that pushes income just over one of these lines can increase Medicare premiums for years. That added cost has to be weighed alongside any future tax savings the conversion might create.

A Cautionary Roth Story

This is where a real-world example brings the point home.

I once worked with a woman to determine the right amount of Roth conversions to do. We carefully mapped out a plan to spread conversions over three tax years so she could stay within reasonable tax and Medicare thresholds.

She was comfortable with the plan. The numbers made sense. We executed the first conversion near the end of the year and agreed to revisit the second one in January.

But after our meeting, she decided to take matters into her own hands.

Rather than following the plan, she converted everything at once. That single decision pushed her income from a moderate tax bracket into much higher ones, triggered additional Medicare premium costs, and permanently locked in taxes that were far higher than necessary.

The intent was good. The outcome was not.

The mistake wasn’t believing in Roth conversions—it was assuming that “more” was always better.

The Real Takeaway for 2026 and Beyond

Roth conversions are not dead. But Roth assumptions are.

Lower tax rates today don’t automatically mean Roth conversions are cheap. A future tax increase isn’t guaranteed. And a zero-tax retirement is not always worth the price paid to get there.

Roth conversions should always be considered—but never assumed.

When done thoughtfully, in the right amounts, and at the right times, they can improve retirement income and flexibility. When done without planning, they can quietly undermine both.

And in retirement, the goal isn’t to win a tax strategy.
The goal is to create a better retirement.

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About the Author:

Jeremy Keil, CFP^®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retirement Today blog and podcast, as well as the Mr. Retirement YouTube channel.

Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times.

Additional Links:

Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
Are Roth Conversions for Retirees Dead in 2026 Because of the New Tax Law? By Jeremy Keil, Kiplinger.com

Connect With Jeremy Keil:

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Disclosures

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Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is indepe...