Should I Do Roth Conversions After I Retire?

What a Roth conversion is and why it feels painful

A Roth conversion is moving money from a pretax retirement account (most commonly a traditional IRA) into a Roth IRA. The catch is upfront: the conversion generally creates taxable income in the year you do it because you are moving untaxed dollars into an account designed for tax free withdrawal later.²

That is why conversions feel like writing a check to the IRS on purpose. And why a lot of retirees ignore them until the first big Required Minimum Distribution shows up and the damage is already baked in.

A few rules that matter before you even talk strategy:

A conversion can be done regardless of your income level (converting is not the same as contributing to a Roth IRA).³

Conversions are reported, and the paperwork matters. If you have any nondeductible basis in IRAs, the taxable portion is tracked using Form 8606, and messing up this form can mean paying tax twice on the same dollars.⁴

Once you convert, you generally cannot undo it the way people used to. Conversions made in tax years beginning after December 31, 2017 cannot be recharacterized back into a traditional IRA.⁵

That last point is huge: a bad conversion year is not a “my bad” year anymore. You want a plan before you hit submit.

Now that the rules are clear, here is the real question: why would a retired firefighter ever volunteer for extra taxable income?

Because retirement taxes are not just about your bracket. They’re about landmines!

The main reasons Roth conversions can make sense after retirement

Conversions are not about chasing a magical “tax free forever” dream. They are about controlling future forced income and protecting flexibility.

Here are the core wins retirees usually chase with conversions, and why they show up hard for pensioned firefighters.

Reducing future Required Minimum Distributions

For many pretax retirement accounts, the government eventually forces distributions. For IRAs, the Required Minimum Distribution rules generally kick in at age 73, with your first RMD due by April 1 of the following year (though delaying that first one can result in two taxable distributions in one year).⁶ Converting some pretax dollars to Roth can reduce the size of those future forced withdrawals because Roth IRAs are not subject to RMDs during the original owner’s lifetime.⁷

Avoiding the Social Security Tax Squeeze

Not every firefighter will receive Social Security Benefits. But if you’re in that club, this section is relevant to you. Social Security taxation is not just “taxed or not taxed.” It phases in. Under current law, depending on “provisional income,” up to 85% of Social Security benefits can be taxable.¹ The kicker is that the thresholds that trigger this are fixed and not indexed, which is one reason the share of beneficiaries paying tax on benefits rises over time.¹

A pension can push your baseline income high enough that adding RMDs later turns Social Security into gasoline on the tax fire. Strategic conversions earlier can lower later RMDs, which can lower future “other income,” which can reduce how much of your Social Security becomes taxable.

Building a tax flexibility bucket

A Roth IRA can function like a pressure release valve later. In years you need extra money for a truck, a roof, helping a kid, or a medical situation, pulling from Roth (if qualified) does not add to your taxable income the way pretax withdrawals do. That can help you avoid accidentally crossing thresholds that trigger bigger taxes or higher Medicare premiums.⁸

Legacy planning under the inherited IRA time limits

If your goal is leaving retirement dollars to adult kids, pretax inherited IRAs can force taxable distributions. The IRS explains that for many designated beneficiaries after 2019, the account often must be distributed by the end of the 10th year after death, with some exceptions for certain eligible beneficiaries. Converting some dollars during your lifetime can shift future growth to an account where heirs may not face the same income tax hit on distributions (though the 10 year timeline can still apply).⁵

The widow problem

Married couples often miss this: after one spouse dies, the survivor frequently ends up filing as single later, with narrower brackets. The IRS explains that a surviving spouse can file jointly in the year of death, and may be able to use Qualifying Surviving Spouse status for two years after the spouse’s death if they meet requirements.⁹ After that, many survivors shift into single rates. That is where “same income, higher bracket” can show up.

If you are building a plan meant to protect a spouse, conversions done while both spouses are alive can reduce the size of future RMDs that might otherwise land on one set of single brackets.

Seguing into the hard part: Every one of those wins is real. But conversions can also backfire.

The traps that turn a “smart conversion” into a bad year

This is where retirees get burned. Not because Roth conversions are bad, but because conversions stack on top of everything else.

Medicare IRMAA and the two year lookback

Medicare Part B premiums have a standard amount, and in 2026 that standard monthly premium is $202.90, according to CMS.¹⁰

But higher income retirees can get hit with income related monthly adjustment amounts (IRMAA). The  (SSA) shows that higher Medicare premiums apply above certain Modified Adjusted Gross Income thresholds, and the SSA states the MAGI used includes adjusted gross income plus tax exempt interest.⁸

The SSA also explains that IRMAA determinations are generally based on tax information from two years prior (for example, 2026 premiums are generally based on 2024 tax return information).¹¹

Translation: a big conversion at 63 can be the reason your Medicare premiums jump at 65. Not the market. Not the pension. Your conversion.

Social Security “tax torpedo” years

Because Social Security taxation phases in, a conversion can increase your provisional income and cause more of your Social Security to become taxable. That can create an effect where the true marginal tax rate on an extra dollar is higher than your bracket alone suggests.

If you plan to convert after you start Social Security, you especially want to model this instead of guessing.

Early retirement health insurance and ACA premium tax credits

This one matters to firefighters because many retire before Medicare age.

The IAFF highlights that firefighters often retire earlier than other workers and can face a gap before Medicare, leaving them needing to secure health insurance in the interim.¹² If you are using Affordable Care Act Marketplace coverage, your income can impact premium tax credits.

A Congressional Research Service report explains that the premium tax credit statute included a temporary provision that expanded eligibility and enhanced subsidies for tax years 2021 through 2025.¹³ And the KFF notes that the enhanced premium tax credit expired at the end of 2025 and has discussed the premium impact of that change.¹⁴

When you retire at 50 to 60 and you are covering insurance on your own, conversions can raise income and potentially reduce subsidies or trigger higher premium costs. That is not a reason to avoid conversions forever. It is a reason to be precise about timing and size.

The under 59½ and five year rule issue

Plenty of firefighters retire in their early 50s. That makes Roth conversion rules sharper.

A Roth conversion has its own five year clock for penalty purposes, and there are ordering rules for Roth IRA distributions. IRS Publication 590 B discusses five year periods and ordering rules for what is considered contributions, conversion amounts, and earnings.⁵ The ordering rules also appear in Treasury regulations.¹⁵

If you convert at 52 and you think you might need those converted dollars at 54, you are playing with the 10% early distribution tax. This is exactly why “convert everything right when you retire” is often a bad idea for younger retirees. It can trap money in the wrong bucket for the years you actually need flexibility.

Paying conversion taxes from the wrong place

A conversion works best when you can pay the tax bill from non retirement dollars. If you withhold taxes from the conversion itself, you are converting less. And if you are under 59½, pulling extra dollars out to pay taxes can trigger penalties depending on how it is done and what accounts are involved.¹⁶

The pro rata rule surprise

If you have both pretax and after tax dollars in traditional, SEP, or SIMPLE IRAs, you cannot just “convert the after tax part.” The IRS looks at your IRAs as one combined pool for calculating what portion of a conversion is taxable, which is why people get blindsided when they try “backdoor” style moves with existing pretax IRA balances.¹⁷ And that is exactly why Form 8606 exists: it is how basis is tracked and how the taxable portion is calculated and reported.⁴

RMD timing mistakes

Once you are subject to RMDs, you generally must take the RMD first, then convert additional amounts. Conversions do not count as RMDs. If you try to convert the RMD amount, you can create a compliance mess.¹⁸

The way you avoid these traps is not by swearing off conversions. It is by running a simple decision drill every year, the same way you would run a size up. Conditions change, and your plan needs to adapt.

A decision drill for retirees considering Roth conversions

This is not a one time decision. For most retirees, it is an annual decision made in smaller bites.