Why spreading Roth conversions over multiple years can
make or break your tax strategy

Most people think the decision is whether to convert to Roth. But the real decision isn’t if, it’s how, and more importantly, when. Because a Roth conversion done at the wrong time can actually increase the total taxes you pay, sometimes significantly. And most people don’t realize that until it’s already happened.

The reason comes down to how the tax code works. Federal income taxes are progressive, each dollar of income passes through lower brackets before reaching higher ones. A single large conversion doesn't benefit from that structure. It blows through every bracket in one year, taxing a significant portion of the converted amount at the highest rates. A multi-year strategy, by contrast, is designed to work with the bracket structure instead of against it.

The chart below illustrates the core issue. A single large conversion in one year pushes income deep into the 32% and 35% brackets, rates that could largely have been avoided by spreading the same total conversion across three to five years and staying within lower tiers.

If you have between $300,000 and $1 million in retirement accounts, this becomes especially important. And if you’re within 5–10 years of retirement, the timing decisions you make now tend to have a much larger impact than people expect.

When most people think about Roth conversions, they focus on the amount. But the IRS doesn’t just tax how much you convert. It taxes when you convert it. Convert too much in one yearnand you may push yourself into a higher tax bracket. Convert too little, and you may miss years where your tax rate was temporarily lower. That’s where the idea of spreading conversions over multiple years starts to matter.

Bracket management is the most visible benefit of a multi-year approach, but it's not the only one. Spreading conversions across several years also preserves three forms of protection that a single-year conversion eliminates immediately.

The difference between a well-structured multi-year conversion plan and a poorly timed one isn’t small. It can mean tens, and sometimes hundreds, of thousands of dollars in lifetime taxes. And once those taxes are paid, there’s no undo button.

This is why our firm's approach to Roth conversion planning is built around multi-year scheduling rather than single-event execution. Using RothEdge, we model the optimal conversion amount for each year of your planning horizon, taking into account bracket targets, IRMAA cliffs, Social Security timing, and projected RMD levels. This allows us to adjust the plan as your circumstances evolve.

The result is a strategy that achieves the same total conversion goal with meaningfully less tax paid along the way and the flexibility to respond to whatever changes between now and completion.