Roth Conversion Strategy: Fill the Bracket, Skip IRMAA
A Roth conversion strategy for retirees: the gap years before RMDs and Social Security, filling the 12% or 22% bracket, IRMAA's two-year lookback, and when not to convert.
Updated 5 min read
Guides · Retirement taxes
Retirement tax guides: Social Security, IRAs and your state
How much of your Social Security is taxable, how IRA withdrawals and Roth conversions change your bracket, and which states tax retirement income. We work from IRS publications and state revenue departments, and say plainly when next year’s figure has not been announced.
2 guides Verified October 23, 2026
What should you know about retirement taxes first?
Taxes in retirement are less about rates than about interactions. One extra dollar of IRA income can make more of your Social Security taxable and push you over a Medicare surcharge threshold at the same time, so the real cost of a withdrawal can be far higher than your bracket suggests.
Our view: plan withdrawals across several years instead of one year at a time. The years between retiring and starting Social Security or required minimum distributions are often the cheapest years you will ever have to move money out of a traditional IRA.
Which retirement taxes questions can you answer right now?
Each of these questions opens a free calculator or reference page that works out the official answer for your own situation in a minute or two. There is no sign-up and nothing to download, and every result shows the official figures and sources behind it, so you can check the math yourself.
Latest retirement taxes guides
Tax-Friendly States for Retirees: Our 2026 Ranking
Tax-friendly states for retirees in 2026, ranked by how they treat Social Security, pensions and IRA income, not just whether they have an income tax.
Updated 5 min read
Calculators for retirement taxes
Is My Social Security Taxable?How much of your Social Security is taxable using the IRS worksheet — and what the new $6,000 senior deduction changes.Open State Taxes on Retirement IncomeWhich states tax Social Security, pensions and IRA withdrawals — all 50 states and DC, with the 2026 rules.Open IRMAA CalculatorWill your income trigger Medicare's IRMAA surcharge? See your tier, the yearly cost, and how far you are from the next cliff.Open Retirement Tax CalculatorYour 2026 federal tax on Social Security, pensions, IRA withdrawals and investments.Open Roth Conversion CalculatorThe tax on a Roth conversion, the room left in your bracket and the IRMAA line two years out.Open Senior Deduction CalculatorYour $6,000 senior deduction after the income phase-out, and the tax it saves.Open Capital Gains Tax Over 65How much of your capital gain is taxed at 0% in 2026, at 15%, and how Social Security changes it.Open Social Security Withholding CalculatorWhich W-4V rate (7, 10, 12 or 22%) covers your tax on Social Security, and how to file it.Open Do Seniors Have to File Taxes?Check the 2026 filing threshold for people 65 and older, including Social Security-only income.Open
Did this answer your question?