If you’re approaching retirement, there’s a tax-planning window you should understand before your last paycheck arrives. The gap between your retirement and age 73, when required minimum distributions currently begin, is often a period when your taxable income drops lower than it has been in decades. Paychecks stop. Deferred compensation winds down. Social Security may not have started. Planning for this window before you retire can give you more options once it arrives.

This stretch can be one of the best opportunities to manage what you’ll owe the IRS over the rest of your life by deciding when to pay tax on money you’ve already saved. A Roth conversion strategy can help you take advantage of that window: you move money from a traditional IRA or other eligible retirement account to a Roth IRA, pay ordinary income tax on the amount converted now, and the Roth can then grow tax-free, with qualified withdrawals tax-free once requirements are met. The key is to start planning before retirement, even if the Roth conversions themselves happen during the years between retirement and RMDs.

When Is the Best Time for a Roth Conversion?

Timing a Roth conversion around the market rarely works out the way people hope. A market dip can make a conversion cheaper in the short term, but the bigger question is the tax rate you pay today versus the rate you’d otherwise pay later. The more reliable signal is your income, not the market.

If you’re still drawing a salary or business income, a conversion could land on top of your highest tax bracket. Once that income stops, and before Social Security and RMDs begin, you may have years where your bracket is lower. Those gap years may offer an opportunity to convert portions of your traditional IRA at a more manageable tax rate.

How Do Roth Conversions Affect My Tax Bracket and Medicare Premiums?

Because a conversion counts as ordinary income, converting too much in one year can push you into a higher tax bracket and potentially trigger Medicare’s income-related monthly adjustment amount, or IRMAA. IRMAA looks back two years, so a conversion in 2026 can affect your Part B and Part D premiums in 2028.

That means the right conversion amount isn’t necessarily the amount that fills your tax bracket. You also need to consider the applicable IRMAA thresholds and the potential increase in future Medicare premiums.

How Much Should I Convert to Roth Each Year to Stay in My Tax Bracket?

There isn’t a universal dollar amount. Start by projecting your taxable income without a conversion, determine the top of the tax bracket you’re willing to use, and calculate how much room remains.

For example, if you have $80,000 of room before reaching the top of your target bracket, that may be your starting point, but not necessarily your final conversion amount. Deductions, other income, Social Security, capital gains, state taxes, IRMAA, and the availability of assets outside the IRA to pay the tax can all change the calculation.

The goal isn’t simply to fill a bracket. It’s to weigh the tax you pay today against potential future tax savings, smaller RMDs, and greater flexibility in retirement.

What Is a Multi-Year Roth Conversion Ladder?

A Roth conversion ladder is a multiyear strategy that involves converting portions of a traditional IRA or other tax-deferred retirement account to a Roth IRA over several years. Each conversion has its own five-year waiting period before the converted amount can generally be withdrawn without penalty, unless an exception applies.

For someone retiring before age 59½, the ladder provides a way to access converted retirement funds during early retirement without triggering the 10% penalty. The strategy requires planning several years ahead.

For individuals already in their 60s, the five-year waiting period is less of a constraint because the 10% early withdrawal penalty no longer applies anyway. However, a multiyear Roth conversion strategy may still be useful for managing tax brackets, reducing future RMDs, and creating tax-free retirement assets.

How Do Roth Conversions Affect Required Minimum Distributions and Heirs?

Every dollar converted before RMDs begin is a dollar that won’t be included in the traditional IRA balance used to calculate future RMDs. For clients managing sizable retirement accounts, that can mean smaller RMDs and more control over their taxable income later in retirement.

There’s a legacy dimension too. Roth IRAs can generally be inherited without income tax on qualified distributions, though many non-spouse beneficiaries must empty the account within ten years. A conversion can therefore shift the tax burden from heirs—potentially during their peak earning years—to you, at a rate you can plan for today.

Is a Roth Conversion Worth It in My 60s?

There isn’t a single right answer. It depends on your state of residence, health, charitable intentions, estate structure, and how much you have saved in traditional retirement accounts.

For someone in their 60s with a substantial IRA, the question is less whether a Roth conversion is good or bad and more about how much to convert, when to do it, and what the trade-offs are.

At ProVise Management Group, we build these decisions into the broader plan, weighing each year’s conversion against your tax bracket, IRMAA exposure, future RMDs, and retirement income needs. If you’re approaching retirement, this window may be worth reviewing before it closes. Reach out to speak with a ProVise CERTIFIED FINANCIAL PLANNER® professional.