> The only problem is that you have to pay tax on the amount rolled over using your tax bracket in that year. Here is what you do... To be clear: When you roll

> The only problem is that you have to pay tax on the amount rolled over using your tax bracket in that year. Here is what you do... To be clear: When you roll pre-tax 401k dollars over to Roth IRA dollars, you pay income tax rates, not capital gains rates. There's no 0% bracket to take advantage of. To do it tax-free, you can roll over only what you deduct each year, i.e. the $25,100 standard deduction in your example. Otherwise you're paying taxes. The point of Roth conversions is to avoid the 10% penalty on withdrawals from other retirement accounts before you're 59.5 years old, not to avoid taxes. You can minimize your taxes by doing the conversions in chunks over years rather than all at once, though, also known as a Roth conversion ladder. The usual plan here is to live on after-tax capital gains and qualified dividends (which have a 0% bracket, as you say) in the early years of retirement while slowly moving money from 401k and traditional IRA accounts to a Roth IRA. When the non-retirement accounts are exhausted, the Roth takes over.