Roth conversions in your sixties: the four-question filter I use before I touch one.

Roth conversions are one of the most talked-about planning moves in the pre-retirement years, and one of the most misapplied.

The basic premise is simple: convert traditional IRA money to Roth now, pay ordinary income tax today, enjoy tax-free growth and withdrawals later. In the right scenario, this is genuinely powerful. In the wrong scenario, you’ve accelerated a significant tax bill for no real benefit.

Half the Roth conversion advice online is built for the wrong client. Running through these four questions before you touch anything tells you which side of that line you’re on.

What You Need to Know Before You Convert a Dollar

According to the IRS, there is no statutory cap on how much you can convert from a traditional IRA to a Roth IRA in a given year. You could convert your entire traditional balance at once. Whether you should is a different question entirely, and the answer depends almost entirely on how four factors line up for your specific situation.

The IRS taxes converted amounts as ordinary income in the year of conversion. That’s the fundamental mechanic. Everything else is about whether the resulting tax bill is worth the long-term trade.

The Four-Question Filter Jeff Uses Before Every Roth Conversion

Question 1: What’s your current marginal rate versus your likely retirement rate?

This is the foundational question. If you’re in the 22% bracket now and expect to be in the 12% bracket in retirement, the math probably doesn’t favor conversion. You’d pay more today than you’d save later.

If the situation is reversed, the case gets considerably stronger. The scenario where conversions make the most sense: you’ve retired but haven’t yet started Social Security or required minimum distributions. Income is lower, the bracket is lower, and there’s still a long runway for tax-free compounding.

Jeff calls the window between retirement and age 73 (when required minimum distributions must begin, per the IRS) the “sweet spot” for conversions. Income drops, the bracket drops, and the clock is still running. Most people with ideal conversion conditions are sitting right in that window and haven’t fully realized it.

Question 2: Do you have funds outside the IRA to pay the tax?

This is the make-or-break question most people skip. If you pay the conversion tax from the IRA itself, you’ve reduced the converted amount and defeated part of the math. Conversion only makes full sense when you can pay the tax bill from a taxable account, keeping the entire converted amount working inside the Roth.

Paying from the IRA is better than not converting at all in some scenarios. But it’s materially worse than paying from outside. Run the numbers on both before you decide.

Question 3: How long is your runway?

Tax-free compounding needs time to overcome the upfront cost. Converting at 68 and needing the money by 73 may not give the math enough room. Converting at 62 with a 20-year spending horizon is a different calculation.

A rough benchmark: a conversion typically needs 7 to 10 years of tax-free growth to break even against the alternative of leaving the money in a traditional IRA, depending on the tax rate difference and assumed growth rate. If your runway is shorter than that, conversion may not make sense regardless of how your rates compare.

Question 4: What does this do to your Medicare premiums?

Conversions add to your modified adjusted gross income. A large conversion in year N triggers IRMAA surcharges in year N+2. Per the Social Security Administration (which administers Medicare Part B premiums), Medicare uses a two-year income lookback to set Part B and Part D costs.

For 2026, a married couple filing jointly with MAGI above approximately $218,000 begins paying IRMAA surcharges. The surcharges increase at several thresholds above that, adding hundreds of dollars per month in additional Medicare premiums per person. A large conversion that crosses one of those thresholds costs real money two years later.

Running the numbers before the conversion is the only way to account for this correctly.

How to Use the Filter in Practice

Work through all four questions before converting anything. The conditions that make conversion worth modeling seriously:

Your current bracket is lower than your projected retirement bracket. You have taxable assets to cover the tax bill outside the IRA. You have at least 7 to 10 years before you expect to need the converted funds. The conversion won’t push your income into a higher IRMAA tier.

If any of those conditions flip, the math changes. That doesn’t mean conversion is wrong, but it means the case is weaker and deserves a closer look.

Jeff runs this filter with clients in their early-to-mid 60s annually, not just once. The variables shift. Brackets change. Retirement timelines move. The right answer in year one isn’t always the right answer in year three.

What This Filter Won’t Tell You

The four questions tell you whether conversion is worth pursuing. They won’t tell you the optimal conversion amount. That’s a function of your specific brackets, your state tax situation, your Social Security timing, and how IRMAA thresholds interact with your income across each year of the conversion window.

That math is worth doing carefully. It changes every time the IRS adjusts bracket thresholds and every time Social Security Administration updates IRMAA income limits.

The Right Answer Is Almost Never Universal

Roth conversions aren’t universally good or universally bad. They’re good for the right person, in the right year, at the right amount. The four questions tell you which of those you are.

If you’re in or approaching the gap years between retirement and age 73, this planning is time-sensitive. That window closes on its own schedule.

Schedule a no-obligation call with Jeff to run through the filter for your specific situation.

The information provided is for educational purposes only and should not be construed as investment advice. Investment strategies should be tailored to individual circumstances, risk tolerance, and goals. Past performance doesn’t guarantee future results. Consult with qualified financial professionals regarding your specific situation. Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Great Valley Advisor Group, a registered investment advisor and separate entity from LPL Financial. © 2026 JeffJudgeCFP.com | Not to be reproduced in whole or in part. All rights reserved.