When should you convert to a Roth?
The clearest cases for conversion are years where your income drops below normal — early retirement, a gap year, a sabbatical, or the window between leaving work and starting Social Security and required distributions. These "tax-rate valleys" are when conversions cost the least and pay off the most.
The clearest cases against conversion are peak-earning years where every additional dollar lands in a 32% or 35% bracket. Wait for the dip and convert then.
Pay the tax from outside the IRA.
This is the single biggest lever. If you pay the conversion tax with cash from a brokerage or savings account, the entire converted amount lands in the Roth and compounds tax-free.
If you pay the tax from the IRA itself, you both shrink the Roth seed and (if under 59½) potentially trigger a 10% penalty on the portion withheld for taxes. The conversion still works, but the math gets noticeably weaker.
Why partial conversions usually win.
Converting your whole IRA in one year almost always pushes you into a higher bracket than necessary. Most planners recommend a multi-year ladder: convert only enough each year to fill your current bracket, then stop.
This is why the calculator above lets you slide the conversion amount. Find the point where your average rate stays below your expected retirement rate, and that's a reasonable annual conversion target.
Second-order effects to model in your head.
A conversion increases AGI, which can: (1) make more of your Social Security benefit taxable, (2) trigger IRMAA — higher Medicare Part B/D premiums, two years later, (3) reduce ACA premium subsidies if you're under 65, and (4) phase out certain credits and deductions.
None of these are deal-breakers, but they're worth checking against your specific situation before doing a large conversion late in your working life.
Common conversion mistakes
- Converting more than fits cleanly inside your current bracket.
- Paying the conversion tax from the IRA itself before age 59½.
- Forgetting the conversion adds to AGI for IRMAA two years later.
- Doing the conversion in a peak-earning year instead of a low-income window.
- Ignoring state taxes — some states tax conversions, others don't.
- Not leaving room for the 5-year clock on each conversion.