Before a Large Roth Conversion: 10 Questions Our Clients Ask

These are the 10 questions retirees and pre-retirees ask most often in TaxesSaved planning meetings before a large Roth conversion, with the 2026 answers. Most of the people asking hold $1 million or more in traditional IRAs and 401(k)s, and they want to move it to a Roth IRA without pushing themselves into a higher tax bracket, raising their Medicare premiums through IRMAA, or making a mistake they can't undo before December 31.

Is it too late to start Roth conversions if I already take RMDs?

No. Your required minimum distribution for the year has to come out first, and it can't be converted, but you can convert more after that. Conversions at this stage start from a higher income, so each one is sized against the top of your tax bracket and the next Medicare IRMAA tier.

How much should I convert each year?

Most plans convert up to the top of a chosen tax bracket and stop. In 2026 the 22% bracket ends at $211,400 of taxable income for married couples filing jointly and $105,700 for single filers; the 24% bracket ends at $403,550 and $201,775. Large balances are usually spread over several years.

Will a Roth conversion raise my Medicare premiums?

It can. Medicare sets Part B and Part D premiums from your income two years earlier. For 2026 premiums, surcharges start above $218,000 of modified adjusted gross income for joint filers and $109,000 for single filers, and the top tier costs $689.90 a month per person for Part B instead of $202.90.

Can my financial advisor and current CPA stay involved?

Yes. Clients often bring their financial advisor into the planning meetings, and the plan is written down so an advisor or outside CPA can review it before anything is executed. If you'd like one firm to do it all, our CPA team can also prepare the return that reports the conversion.

Can a business deduction offset the tax on a Roth conversion?

Sometimes. A loss from a business you materially participate in can offset ordinary income, including conversion income, up to the amount you have at risk. The excess business loss limit caps the offset at $512,000 for joint filers and $256,000 for other filers in 2026; the rest carries forward.

What does material participation mean?

It's the IRS test for whether you actually work in a business. Two common ways to meet it are working more than 500 hours in the year, or working more than 100 hours and at least as much as anyone else. Keep a log of the hours you spend.

What happens if the business investment doesn't work out?

The cash you put in can be lost, and if part of the purchase is financed you may be responsible for that debt. Depreciation can also be recaptured as income when the asset is sold. A deduction is only worth it if the business makes sense on its own.

Does a large Roth conversion increase my audit risk?

No one can promise a return won't be examined. What holds up is documentation: the conversion paperwork from your custodian, contracts and placed-in-service dates for any business assets, and your record of hours worked.

What's the deadline for a 2026 Roth conversion?

December 31, 2026. A conversion counts as income in the year the money moves and can't be reversed. Any business asset meant to create a 2026 deduction also has to be placed in service by December 31.

Should I convert now in case tax law changes?

Under current law the 2026 rate schedule is permanent and the estate tax exclusion is $15 million per person, while the extra $6,000 deduction for people 65 and older ends after 2028. Congress can change any of these. A conversion locks in today's known rate on the amount you convert, which is a reason to plan now, not a reason to convert everything at once.

How TaxesSaved answers these questions for your numbers

The TaxesSaved CPA team, with Big Four backgrounds, turns these answers into a written Roth conversion plan for your household, puts it in place, and prepares the returns that report it, for clients in all 50 states. For real examples, read our six Roth conversion case studies from 2026.

To see your own numbers first, run the free Retirement Tax Calculator, or watch the free Roth conversion and RMD webinar.

Questions come from TaxesSaved planning meetings held in 2026. Figures are federal and come from IRS Revenue Procedure 2025-32, IRS guidance on the senior deduction, and SSA's 2026 IRMAA tables, as of November 3, 2026. This article is for education only and isn't tax, legal or investment advice. Talk with a qualified tax professional before you act.