Retirement tax questions

The questions retirees ask, explained

You've heard about Roth conversions, Social Security timing and Medicare surcharges. Whether each one pays off depends on your own household. These guides explain what goes into each decision, with a worked example using the 2026 figures and the official sources behind them.

• Should we convert to a Roth, and how much?Tax now or tax later: what a conversion costs this year, and what it changes for decades.
• When should each of us start Social Security?Every start age from 62 to 70, for both of you, with the survivor benefit and the taxes around it.
• Will Medicare surcharges (IRMAA) hit us?The 2026 tiers, the two-year lookback, and what one dollar over a line costs.
• What happens to our taxes when one of us dies?The survivor files as single, often on most of the same income. A worked example of the "widow's penalty".
• Before Medicare, how do we keep Marketplace (ACA) help?Retiring before 65: the 2026 subsidy cliff, and how withdrawals and conversions count toward it.
• Should we give to charity from the IRA (QCDs)?Giving straight from an IRA keeps the gift out of income. A worked example next to a cash gift.

More questions Taxtirement helps with

• How much more income fits this year before taxes or Medicare premiums jump? The app shows the room left before the next bracket, Medicare tier and ACA cliff, on the This Year screen and a home-screen widget. The brackets are on the federal rules page.
• What if we move to another state? Add a planned move and the year, and the plan uses the new state's rules from then on. See how each state taxes retirement income.
• What will our heirs owe? Add your heirs and roughly what they earn. The 10-year rule is worked out for each one, and every scenario shows what's left after the tax they'd pay.