Should You Do Roth Conversions Before You Start Social Security?

For many people, the answer is yes. If Roth conversions are part of your retirement plan, or you're considering them, beginning those conversions before you claim Social Security is often prudent. Why? Because in many situations, the tax from a Roth conversion has a tax ripple effect: it can cause your Social Security paycheck to be taxed, or taxed more heavily than it would have been otherwise. Here's how that works.

This piece is not meant to argue for or against Roth conversions. Whether to convert at all, and how much, is a broader topic covered in should you convert to a Roth IRA. The low-income years between retirement and required distributions are covered in the retirement tax planning window and in how to maximize tax efficiency in retirement. What follows is about one thing: how the timing of your Social Security claim and the timing of your conversions affect each other.

Why a Roth conversion before Social Security costs less

A Roth conversion is taxed as ordinary income in the year you do it. IRS Publication 590-B is explicit that converted amounts are includible in gross income. So there's no way around that tax. But the tax that can be controlled is the taxation of your Social Security benefits. And that's where the timing of Roth conversions becomes relevant. The IRS test for taxing benefits is in Publication 915. It adds half of your benefits to all your other income, including tax-exempt interest. On a joint return, if that total is over $32,000, up to 50% of benefits can become taxable. Over $44,000, up to 85% can. For single filers the lines are $25,000 and $34,000.

Conversion income is "other income" in that test. Before you claim, a conversion adds only itself to your taxable income. After you claim, it can pull Social Security into taxable income behind it.

Here is a simple comparison on a joint return. The couple has $50,000 of combined Social Security benefits and no other income besides the conversion.

Convert $60,000 before benefits start. The conversion adds $60,000 to taxable income. Social Security is not in the picture yet, so none of the benefits are taxable.

Convert the same $60,000 after benefits have started. The conversion still adds $60,000. It also pushes the couple over the Pub 915 thresholds, so Social Security becomes taxable too. Up to 85% of benefits can be taxed. On $50,000 of benefits, that ceiling is $42,500.

In this example, the worksheet lands on that ceiling. Taxable benefits = $42,500. Add the conversion, and taxable income rises by $102,500.

Same conversion. Same account. About 70% more income gets taxed, only because benefits were already being paid.

Where this wouldn't make a difference is for someone whose retirement income sources will never let them avoid taxation of Social Security benefits. For example, someone with a large pension, or a large taxable portfolio that generates substantial dividends and interest. In those cases, delaying Social Security still might be the right move, but it has nothing to do with Roth conversions per se. They might delay for the delayed retirement credits, or delay one spouse's benefit so they can manage AGI and Medicare premiums.

Delaying Social Security lengthens the conversion window

Every year you live on savings instead of benefits is another year when a conversion is taxed on its own. Claim at 62 and the clean years end at 62. Claim at 70 and you may have eight of them.

According to SSA, for anyone born in 1943 or later, benefits rise 8% for each year you wait past full retirement age. The increase stops at 70. If your full retirement age is 67, waiting to 70 adds 24%.

The two decisions reinforce each other. Delaying makes room for conversions. Conversions shrink the pre-tax balance that later RMDs come from. A smaller RMD stacked onto that larger benefit can mean less of the benefit gets taxed down the road, unless other income already pushes it to the 85% ceiling.

That is the core of a Roth conversion strategy for ages 62–70. The claiming age is part of the conversion plan, not a separate question.

It also has a cost. The spending has to come from somewhere for those years. If it comes from an IRA, those withdrawals use up the same low brackets the conversions were supposed to use.

Does a Roth conversion count as income for Social Security?

People mean two different things by that question, and the answers are opposite.

For taxing your benefits: yes. As shown above, conversion income counts in the Pub 915 test.

For your benefit amount and the earnings test: no. SSA's rules for working while receiving benefits count only wages from a job or net self-employment profit. They specifically exclude pensions, annuities, and investment income. A conversion isn't wages.

So a conversion won't trigger the earnings-test reduction that applies before full retirement age. The 2026 limit for that test is $24,480. And it won't raise your benefit either. SSA only recalculates a benefit when a new year of work earnings ranks among your highest. A big conversion year looks like a big income year to the IRS and like nothing at all to SSA's benefit formula.

Conversions at 63 or later show up in Medicare premiums at 65

Medicare's income-related surcharges look back two years. SSA generally sets 2026 premiums from 2024 tax returns. A conversion in the year you turn 63 is the income that prices your Medicare at 65.

For 2026, the surcharges start above $218,000 of modified AGI on a joint return. For other filers, they start above $109,000. Modified AGI is AGI plus tax-exempt interest.

The first surcharge tier adds $81.20 a month to the standard $202.90 Part B premium. It also adds $14.50 a month for drug coverage. Those amounts apply per person on Medicare.

The surcharge works in tiers. A dollar over a line costs the whole step. That makes conversions in your 60s a sizing exercise as much as a yes-or-no one.

One more detail matters. SSA lets you ask for a new determination after certain life-changing events, such as stopping work. A Roth conversion isn't on that list. Retirement itself may get your final salary year reconsidered. The conversion you chose to do won't be.

The five-year rules, briefly

If the plan is to live on savings and convert, keep the converted dollars invested rather than spending them right away. Per Publication 590-B, each conversion starts its own five-year period for the 10% additional tax. That tax doesn't apply once you're 59½.

Separately, for earnings to come out tax-free, the account has to be past the five-year period that begins with your first Roth contribution year. Most people in their 60s clear the first rule automatically. The second one is worth checking before you rely on the Roth for spending.

When converting before Social Security isn't worth it

Results depend on your individual circumstances, and tax rules can change. These are the situations where converting before Social Security, or converting at all, usually does not pay:

• There's no cash outside the IRA. If delaying Social Security means living off IRA withdrawals, and the conversion tax also has to come out of the IRA, the window you're trying to use gets spent on living costs. Those withdrawals usually erase the tax savings.
• Your tax rate now is the same as or higher than your rate later. A pension that already fills the lower brackets, or an IRA modest enough that future RMDs will be small, can make today's conversion the more expensive option.
• Your heirs are in lower brackets than you. Paying tax at your rate so that children in lower brackets inherit a Roth can cost the family more than leaving them the IRA.
• The conversion would cross a Medicare tier for a small amount of benefit. Converting $5,000 past a surcharge line is often a bad trade. Stopping just under it and continuing next year usually isn't.
• You need benefits early. Health, a shorter expected lifespan, or simply needing the income can make claiming early the right call. Once benefits start, conversions get more expensive for the reasons above.

None of these come from a rule of thumb. They come from comparing your bracket now, with and without benefits, against the bracket you're likely to face once RMDs and a larger benefit arrive together.

Roth conversion strategy after retirement: the order is the decision

Decide your claiming age and your conversion amounts before you file for benefits. Filing is hard to undo.

If you can live on savings for a few years, convert first and claim later. If you cannot, or if your future brackets will not be higher, find that out before you convert.

If you're in your 60s and haven't filed yet, run that calculation first. At Heritage Wealth in Naperville, we work through that timing with retirees across Chicago's western suburbs in retirement tax planning.