Beth Pinsker

Wed, May 21, 2025, 7:00 AM7 min read

If you’re eager to jump on the Roth bandwagon, it may be frustrating to go through the process and find roadblocks. But sometimes, you run the math and it just doesn’t make sense for you.

Roth IRA conversions are not a good idea for everyone. They work in certain circumstances where the tax arbitrage comes out in favor of paying the tax now rather than paying it later. It’s not simple math, and it involves a lot of guesswork about the future, plus it requires a lot of cash on hand. And the transactions can be tricky — paperwork and strict timetables are involved.

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“It’s like French cooking,” financial planner Thomas Duffy said. “There are so many difficult techniques to master.” MarketWatch spoke with Duffy, who is based in New Jersey, as he was preparing for a call about Roth conversions with a client for whom there were a slew of considerations.

The client is 68 and just retired. He wants to continue working part-time and start collecting Social Security. His spouse is still working. Duffy wanted to convince him to wait two more years, until he turns 70, to claim Social Security, and in the meantime to convert some significant IRA money to a Roth using a stash of $200,000 in cash to cover the tax bills. “I will tell him that his tax bill for this year will be close to the 12% bracket, but once his spouse retires and they start taking required minimum distributions, they’ll be at least in the 24% bracket,” Duffy said.

Doing Roth conversions for a few years now could save that couple 2% on their taxes in later years.

But Duffy has other clients for whom the math doesn’t make sense. And whenever I write an article about Roth conversions — which entail taking money out of a tax-deferred account like a 401(k) or IRA, paying the tax on the income and then moving the money to a Roth account — I get lots of letters from people outlining their circumstances and then asking why the conversion won’t work out for them, or why their adviser is telling them not to do it. Here are four cases where readers ran into obstacles to making the Roth conversion strategy work for them.