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Tax Planning When You Retire

The first few years of retirement are often the best Roth conversion window of your life.

Katie Gorles
Written by
Katie Gorles
Updated April 22, 2026

The Roth conversion window

Between retirement (or part-year retirement) and age 73 when RMDs start, you may have the lowest income of your adult life. Filling up to the top of the 12% or 22% bracket each year with Roth conversions can save substantial tax later.

IRMAA awareness

Medicare Part B and D premiums increase with income (IRMAA). Roth conversions and large retirement account distributions can push you into higher IRMAA tiers. Planning around the brackets matters.

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Common questions

When should I start Social Security?
Not strictly a tax question. Delaying increases the benefit but defers income. We model the tax side; you should also get a financial advisor's view on the longevity side.

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