Should You Jump on the Roth Conversion Bandwagon? A Financial Adviser Weighs In

Roth conversions are all the rage, but what works well for one household can cause financial strain for another. This is what you should consider before moving ahead.

By Steven L. Rich, RICP®, CLTC®, NSSA®, CF2

published 15 February 2026

in Features

Roth conversions have become a popular topic in retirement discussions, and for good reason.

With concerns about future tax rates, required minimum distributions (RMDs) and the tax treatment of inherited retirement accounts, many investors are taking a closer look at whether converting traditional retirement assets to a Roth IRA makes sense.

At its core, a Roth conversion involves moving money from a traditional IRA or 401(k) into a Roth IRA and paying income taxes on the converted amount today.

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In exchange, future growth and qualified withdrawals from the Roth account can be tax-free. While the concept is simple, deciding whether a Roth conversion is the right move requires careful analysis.

Why some retirees consider Roth conversions

One of the primary appeals of Roth IRAs is tax flexibility. Unlike traditional retirement accounts, Roth IRAs do not require minimum distributions during the account owner's lifetime. That allows retirees to control when and if they take withdrawals, which can be especially valuable when managing taxable income.

Roth accounts can also help reduce future tax exposure. Retirees who expect tax rates to rise, either due to legislative changes or increasing income later in retirement, may benefit from paying taxes now at a known rate.

In addition, Roth IRAs can be an effective legacy tool, since beneficiaries generally receive tax-free withdrawals, provided certain conditions are met.

For some, Roth conversions also offer a way to manage large balances in tax-deferred accounts. RMDs increase with age, and sizable withdrawals later in retirement can push income into higher tax brackets or affect the taxation of Social Security benefits.

About Adviser Intel

The author of this article is a participant in Kiplinger's Adviser Intel program, a curated network of trusted financial professionals who share expert insights on wealth building and preservation. Contributors, including fiduciary financial planners, wealth managers, CEOs and attorneys, provide actionable advice about retirement planning, estate planning, tax strategies and more. Experts are invited to contribute and do not pay to be included, so you can trust their advice is honest and valuable.

Compare today's tax rate with tomorrow's. A practical starting point is comparing your current tax bracket with what you expect your tax situation to look like in the future. If your current income is temporarily lower, perhaps early in retirement or during a career transition, converting during those lower-income years may be advantageous.

On the other hand, converting large amounts while you are still earning peak income could result in paying higher taxes than necessary.

A thoughtful approach often involves partial conversions over multiple years rather than converting everything at once.

Understand how conversions affect other taxes. One detail retirees sometimes overlook is how a Roth conversion can affect other parts of their tax return. Increasing taxable income may impact the taxation of Social Security benefits or trigger higher Medicare premium surcharges.

Before moving forward, it is important to model how a conversion would affect total taxable income for the year. A conversion that looks attractive on paper could have unintended consequences if it pushes income across key thresholds.

Confirm you have the liquidity to pay the tax bill. Roth conversions require paying taxes on the converted amount in the year the conversion takes place. Ideally, those taxes should be paid using funds outside of the retirement account.

Using retirement assets to cover the tax bill reduces the amount that ultimately makes it into the Roth account and can diminish the long-term benefit of the strategy.

Retirees considering conversions should assess whether they have sufficient cash reserves or taxable assets to handle the tax obligation comfortably.

Consider timing and pacing. Many successful Roth conversion strategies are built gradually. Rather than converting a large balance all at once, some retirees convert smaller amounts each year to stay within a desired tax bracket.

This approach allows for greater control and flexibility. It also provides opportunities to adjust as tax laws, income needs or market conditions change.

Timing conversions during market downturns may also reduce the taxable value of the conversion, although this should not be the sole reason for moving forward.

What clients often overlook

Many people approach Roth conversions with enthusiasm after reading about the benefits, but without fully understanding the tradeoffs. One common misconception is that a Roth conversion automatically leads to lower taxes overall. In reality, the benefit depends on future tax rates, spending needs and how long the assets remain invested.

Another overlooked factor is time horizon. Roth conversions tend to be more effective when there is enough time for tax-free growth to offset the upfront tax cost. For retirees who expect to need the funds in the near term, the math may not work as favorably.

Married couples may also focus on the appeal of leaving tax-free assets to heirs without considering the annual cash flow needed to support ongoing conversions. Without adequate planning, even a well-intentioned strategy can strain household finances.

The bottom line

Roth conversions can be a powerful tool, but they are not right for everyone. The decision depends on a combination of current income, future tax expectations, available liquidity and long-term goals.

For retirees and pre-retirees, the most effective approach is often a coordinated one that looks at the full financial picture rather than focusing on a single strategy in isolation.

Taking the time to evaluate how a Roth conversion fits into your broader retirement income plan can help ensure that the decision supports both near-term stability and long-term flexibility.

Disclaimer

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

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After more than a decade and a half in the financial industry, Steven L. Rich, RICP®, CLTC®, NSSA®, founded NSBRS to bring something different to the area — a personal, independent approach to retirement planning. Many of Steven’s clients have recently moved to Florida from states like New Jersey, New York, Pennsylvania and Delaware. They’ve traded cold winters for warm weather and beach days — and now they’re looking for someone local to help them navigate Social Security, Medicare, income and taxes in retirement.