Should I Do a Roth Conversion Before RMDs Start? The Window, and the Medicare Trap

"Everybody keeps telling me to convert some of my IRA before my required distributions start. Is that actually true for me?"

I hear some version of that almost every week. Somebody heard it on the radio, a neighbor did it, or I made that suggestion to someone as their advisor, even. Once that idea's been hatched, it feels like a deadline is bearing down. Perspective on this is important, though. There really is a window, and for some households it is a genuine opportunity to place themselves in a more tax-advantaged position. However, a Roth conversion is two parts: The Decision and The Consequence. The latter is what trips people up, and one of the areas they never think of it is Medicare.

What are RMDs, and why do they matter here?

A required minimum distribution, or RMD, is the minimum amount you are required to withdraw from your pre-tax retirement accounts each year once you reach a certain age. It is calculated from your account balance at the end of the prior year and your life expectancy, so the dollar amount changes every year. Whatever comes out is taxed as ordinary income.

Traditional IRAs, 401(k)s, and traditional TSP balances all fall under that rule. Roth IRAs do not, and that is a big part of why this whole conversation exists.

Under current rules, RMDs generally begin at age 73, and the IRS keeps a full explainer if you want the fine print. The short version for our purposes: at some point, the choice about when money comes out of those accounts stops being yours.

What is the Roth conversion window before RMDs?

There really is no defined "Roth Conversion Window." It's really just the time before you're forced to take your RMDs. However, most refer to it as the time from when you retire to when you begin your RMDs. In that "window" you're dropping the biggest line item off your tax return, your wages. What's left is Social Security, maybe a pension, maybe some interest and dividends, maybe income from an annuity. For a lot of households in middle Georgia, that adds up to a much smaller taxable income than they had at age 60.

Georgia gives retirees another break on top of that. The state lets each resident exclude up to $65,000 of retirement income at age 65 and older, and up to $35,000 at ages 62 through 64. For a married couple both over 65, that is a meaningful amount of retirement income sheltered from state tax. How a conversion interacts with that exclusion is worth working through with a tax professional, because the state and federal rules do not line up neatly.

This potential reduction in taxation creates an opportunity to get ahead of RMDs by using Roth conversions, because any conversions you do will be counted as regular income on that year's taxes.

What does a conversion actually do to my taxes?

It moves the tax bill forward. When you convert money from a traditional IRA to a Roth IRA, the amount you convert is generally added to your income for that year and taxed as ordinary income. The one exception is money you already paid tax on, such as nondeductible contributions, which does not get taxed a second time. You are volunteering to pay tax now on money you would otherwise have paid tax on later.

That is the whole trade. Pay a known rate today instead of an unknown rate down the road. Sometimes that is a good deal. Sometimes it is not.

Why do RMDs change the math?

Two reasons. First, once RMDs start, the IRS dictates how much of your pre-tax money you need to distribute on an annual basis, whether you need it or not, and that income stacks on top of everything else you have.

Second, a conversion does not count as a required minimum distribution. Once you turn 73, if you want to do Roth conversions, they'll have to be done after the RMD has been satisfied for that year. You cannot convert a required minimum distribution, so the flexibility you had before 73 is not the same flexibility you have after.

Can a Roth conversion raise my Medicare premiums?

Yes, and this is the part that catches people. Medicare looks back two years at your tax return to decide whether you owe an income-related monthly adjustment amount, or IRMAA. For 2026 premiums, Social Security generally uses your 2024 return. The standard Part B premium for 2026 is $202.90 a month, and IRMAA begins above a modified adjusted gross income of $109,000 for an individual filer or $218,000 for a married couple filing jointly.

Think of it like a speed camera two counties back. You already drove past it. The ticket just hasn't shown up in the mailbox yet.

There is a process for asking Social Security to reconsider using Form SSA-44 when a life-changing event drops your income, things like retirement, the death of a spouse, or the loss of a pension. Deciding to do a Roth conversion is not on that list. A conversion is a choice, so it does not qualify as a life-changing event.

There is a quieter version of the same trap. Retirees 65 and older can currently claim an additional deduction of up to $6,000 per person, but it phases out as modified adjusted gross income rises above $150,000 for joint filers. A conversion large enough to reach that phaseout can quietly cost you deduction dollars on top of the tax on the conversion itself.

Should I just convert enough to fill up a tax bracket?

That is the rule of thumb you hear most, and it is a starting point, not an answer. For 2026, the 22 percent bracket for married couples filing jointly begins above $100,800 of taxable income, and the 24 percent bracket begins above $211,400. Filling a bracket does that, and only that. It doesn't take into account how it affects your Medicare, your state tax, how much of your Social Security gets taxed, and a whole host of other things that can show up on later returns, some of them two years down the road.

Here's a hypothetical, and I want to be clear that it is only an illustration and not a recommendation.

Let's say a couple in Warner Robins, both 66 and both retired, expect about $60,000 of taxable income this year. On paper they have roughly $40,000 of room before they reach the 22 percent bracket.

If they only convert $40,000 and fill that gap, then they'll most likely just owe taxes on the $40,000 they converted. IRMAA would not come into play for this couple at that income level.

Now let's say they convert $150,000 instead. The picture changes. Part of it gets taxed at a higher rate, the senior deduction starts phasing out, and they get uncomfortably close to Medicare territory. Same couple, same window, very different outcomes.

Questions worth answering before anything moves

• What will your total taxable income actually be this year?
• How close is your household to the IRMAA threshold, remembering the two-year lag?
• When do your RMDs begin, and how big are they likely to be?
• Do you expect taxes to go up or down in the future?
• If one spouse passes, does the survivor end up filing single at higher rates?
• Do you have cash outside the IRA to pay the tax bill?
• Are you converting for yourself, or for the kids who will inherit it?

That last one deserves its own thought. A Roth left to a child still comes with a ten-year withdrawal deadline, but the withdrawals are not the tax event a traditional IRA would be. If legacy is the point, it belongs in the same conversation as which assets are best to leave your heirs and when you claim Social Security.

Common questions about converting before RMDs

Can I convert an IRA after I retire?

Yes. There is no age limit and no earned income requirement to convert a traditional IRA to a Roth IRA. The amount you convert is generally added to your income for that year. In fact, more and more people who are literal decades away from retirement are using this time to do Roth conversions on old retirement accounts from previous jobs they've left. This isn't just a strategy for someone who's 60 and up. Younger people are doing this nowadays as well.

How many years later can a conversion affect Medicare?

Two. Medicare uses your tax return from two years earlier to set IRMAA, so a conversion done this year shows up in the premium calculation two years from now.

Should federal retirees with a TSP think about this differently?

Somewhat. A traditional TSP balance carries the same pre-tax problem an IRA does, and the same RMD timing, but rollover mechanics and FEHB coordination add moving parts. If you retired out of Robins Air Force Base, it is worth mapping those pieces together rather than one at a time.

The bottom line

A Roth conversion is not a one-time tax trick. It is a multi-year plan, and the years before RMDs are when you have the most room to build one. It is also permanent. Conversions made after 2017 cannot be recharacterized, so there is no undo button.

If you are somewhere in that window and nobody has ever mapped it out for you, that is exactly the kind of thing we sit down and work through at Crossroads Financial, alongside your CPA. No pressure, no product pitch. Just numbers on paper so you can see what you are actually deciding.

This article is educational and is not tax, legal, or investment advice. Tax rules change and every household is different, so please consult a qualified tax professional before making a conversion decision. Crossroads Financial works alongside your tax and legal advisors rather than in place of them.