Between the year you stop working and the year Social Security starts, your taxable income is usually the lowest it will ever be. This sizes a multi-year ladder that fills the bracket you choose, and shows what is still sitting in the traditional account when required distributions begin at 73.
For most of a working life there is no room in the lower brackets, because salary already fills them. After required distributions begin at 73, there is no room either, because the distributions fill them whether you want the income or not. In between sits a window where earned income has stopped and forced income has not started, and that window is the only time most people can move money at a rate they choose.
A ladder uses that window deliberately: convert enough each year to reach the top of a chosen bracket and no further, repeat until the window closes. Every dollar moved is a dollar that will not be taxed again, will not be forced out at 73, and will not raise the taxable portion of Social Security later.
Medicare sets premiums from income two years prior, so conversions made at 63 and 64 land on the premiums you pay at 65 and 66. Those thresholds are cliffs rather than slopes: one dollar over raises the premium for the entire year. It is the most common way a well-intentioned ladder costs more than it saves, and the reason starting early matters as much as sizing correctly. The IRMAA calculator shows where the lines sit.
Federal ordinary brackets only, at 2026 figures, with the standard deduction. It does not model state tax, capital gains stacking, the taxable portion of Social Security, ACA premium subsidies during the same years, or the survivor's move to single-filer brackets. Each of those can change the right answer, and the last two often change it the most.
For a single year rather than a ladder, use the Roth conversion calculator. If you are retiring before 65, conversions also raise the income that sets your ACA subsidy, which is a direct tradeoff worth seeing together rather than separately; the health insurance gap before Medicare covers that collision, and the planbend app models both at once against your own numbers.