Optimize Your Roth Conversion Strategy With Real Financial Modeling
The Boldin Retirement Planner Gives You Access to Tools Used by Financial Planners
Roth conversions can reduce lifetime taxes — but the timing and amount matter. Boldin’s Roth Conversion Explorer analyzes your complete financial plan to show when and how much to convert.
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Why Roth Conversions Matter
Roth conversions can:
Reduce the taxes you pay over your lifetime
Prevent large Required Minimum Distributions later
Help you control your retirement tax bracket
Increase what you leave to heirs
Strategic conversions often shift income from higher-tax future years into lower-tax years today. But the right strategy depends on your income, retirement timing, Social Security, and future RMDs. That’s where modeling helps.
What the Roth Conversion Explorer Can Do
The Boldin Roth Conversion Explorer:
Projects your income and taxes across retirement
Identifies years when conversions may reduce lifetime taxes
Tests multiple strategies (tax bracket limits, lifetime tax minimization, estate goals)
Shows the impact on lifetime taxes and net worth
Behind the scenes the planner models your income, Social Security, RMDs, and taxes year-by-year to identify optimal conversion schedules.
How to Get Started
Strategizing Roth conversions requires that you have defined a robust financial plan. If you are already a Boldlin user, use the Digital Coach, Plan Accuracy and Plan Completion metrics to make sure that your plan is robust and up to date.
If you are new to Boldin, getting started is easy. We’ll guide you step through creating a plan and your financial confidence will grow each step of the way. This step can take anywhere from 30 minutes to days, depending on how detailed you want to be.
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How to Access to the Roth Conversion Explorer in Boldin
The Roth Conversion Explorer in Boldin is a useful tool for modeling and planning IRA conversions. This article will guide you on how to access this feature, provide troubleshooting tips, and highlight important usage considerations.
To locate and open the Roth Conversion Explorer:
Open your Boldin planner on a desktop computer or tablet.
In the left-hand navigation menu, click on Explorers.
From the list of Explorers, select Roth Conversion Explorer.
See Your Roth Conversion Strategy
Create your Boldin plan to test Roth conversion scenarios using your real numbers.
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How to Use Boldin's Roth Conversion Explorer
Technical Details
What Strategies are Available?
Goal Based Strategies
When choosing the highest estate value strategy and the lowest lifetime tax liability strategy, the Explorer will cycle through all available federal tax brackets, analyze the impact of converting within each bracket on the selected goal, and select the optimal bracket for that specific strategy.
The Explorer will inform you if it is not able to provide a plan that achieves a higher estate value or lower lifetime tax liability than your current plan.
Rule Based strategies
When choosing the tax bracket limit strategy and the IRMAA bracket limit strategy, the algorithm will recommend converting just enough to “fill” your bracket until there are no more opportunities or you run out of pre-tax dollars. These strategies will respect thresholds and may result in a lower estate value or higher lifetime tax liability depending upon the limit you choose. As a result you may see a negative result for one of those metrics, but you will not receive a message stating that they could not find a better solution for you, rather you will always see a result because you have set the threshold. For example, if constrained conversions that respect income thresholds like IRMAA are a priority, selecting strategies like 'Tax Bracket Limit' ensures alignment with these parameters while maintaining tax efficiency.
What is the value in offering 4 diverse strategies?
As the saying goes, “Personal finance is personal.” Here at Boldin we take that to heart by offering multiple planning models, so users can choose the approach that best fits their unique situation
How are the pre-tax source accounts chosen?
You do not have the ability to directly select source accounts.
The Explorer makes an assumption that all Traditional IRA accounts and all other pre-tax accounts are eligible for conversion. This may be an issue if you have non-eligible tax-advantaged accounts modeled in your plan. In that case you should exclude the account from the withdrawal strategy.
The Explorer’s logic for selecting source accounts is to select the pre-tax account with the highest rate of return, as this provides the most tax-free growth. If there are multiple accounts with the same rate of return, the order then factors in your withdrawal order settings:
With Traditional withdrawal order: accounts are prioritized alphabetically by account name.
Under the Custom withdrawal order: (available to PlannerPlus members): accounts follow the specific order you've defined through the drag-and-drop interface in the Money Flows section.
How are the destination Roth accounts chosen?
If you don't currently have a Roth account in your plan, the system will create one for you with the default rate of return of 8.08%. If you'd like greater control of the rate of return, you may want to create a placeholder Roth account prior to running the Explorer.
We recommend carefully reviewing the rate of return assumptions on your pre-tax and Roth accounts. If the Roth account has a higher rate of return, that often comes with increased volatility and a wider range of outcomes with higher potential upside but also greater downside risk in the Monte Carlo simulation.
What are the Tax Payment Options?
The Explorer's suggestion for Roth conversions depends on your answer to "Is it okay to pay for the tax liability of Roth conversions with converted funds?"
Yes. If your after-tax funds are depleted, the algorithm may suggest conversions which require pre-tax funds to pay conversion taxes.
No. If your after-tax funds are depleted, the algorithm will not suggest conversions which require pre-tax funds to pay conversion taxes.
When the Optimized Plan is applied to your scenario, the initial assumption is that taxes are paid from funds outside the IRA (after-tax funds). Taxes are paid according to our established plan order of operations, your chosen withdrawal strategy, and withdrawal order. Should additional funds be needed, the Planner will then use funds from tax-deferred accounts.
If you would like to model the tax coming from the source account, you have a couple of options.
You may want to exclude the after tax accounts from withdrawals so that tax-deferred accounts will be tapped to fund taxes once the after-tax accounts are depleted. We don't suggest increasing the conversion modeling to account for this.
If you wish to leave the after-tax accounts open to pay expenses, you should model the Roth Conversion as a Transfer to a Roth account. And then add a Transfer from the Roth account to a cash account that funds expenses.
NOTE: You do not have the ability to control the tax payment selection when using the customized order feature.
Additional Details
Savings balances are not tax adjusted. Tax-deferred account balances, which may incur a tax liability for a surviving spouse or other heirs, are not adjusted in Boldin's calculations. In real life, $1 in a Roth account may provide more "spendable money" than $1 in a tax-deferred account. This is not taken into consideration in the software.
The Roth Conversion Explorer strategy removes all future modeled Roth Conversions in your Plan before generating a suggestion.
If your after-tax accounts have a higher growth rate than your tax-deferred accounts, the Explorer may not suggest an optimized plan because allowing the after-tax money to grow may result in a higher net worth.
Roth conversions may not be suggested if the tax payments reduce the after-tax funds below the protected amount specified in your plan.
The Explorer will limit Roth conversion suggestions when they result in an unfunded One Time Expense or Transfer from a specific account. You may want to run the Explorer prior to adding those items. You also have the option of modeling One-Time Expenses from your withdrawal order to avoid this issue.
The software does not feature the Affordable Care Act/Premium Tax Credits. You may add the reduction in/loss of tax credits due to conversions as an expense.
Roth Conversions do not satisfy RMD requirements.
What are the Assumptions around conversions prior to age 59.5?
You may see suggestions from workplace accounts before age 59½. Check with your plan provider to confirm eligibility.
The Explorer does not consider Early Distribution Penalties or the 5-year rule.
How are current year conversions taken into account?
If you have made a partial conversion early in the year, enter the conversion in the prior month and the Explorer will surface your remaining opportunity. Once the date of a conversion is past, the tax liability will remain but you must adjust your account balances.
It's essential to use your own discernment and consider your investing and planning temperament prior to executing any financial strategy. We also recommend that you validate your strategies with a tax professional or your tax software prior to taking action. By revisiting one-time expenses, aligning your withdrawal order with conversion goals, and leveraging strategies like 'Tax Bracket Limit,' you can further fine-tune the Roth Conversion Explorer’s recommendations to better match your financial needs.
Exploring manual conversion strategies can offer additional options for increasing Roth balances, even if not directly recommended by the tool.
About Boldin
Boldin helps people gain clarity and confidence about their financial future. The Boldin Planner brings together income, taxes, investments, Social Security, and spending into a single financial model so users can explore decisions, test scenarios, and build a plan that supports the life they want.
We connect the math of money to the meaning of life.
It’s like having a financial planner at your fingertips.
Want help with set up? We have options. Start by chatting with Boldin’s AI, joining one of our communities on Facebook or Reddit, or attending one of our getting started classes. You can also sign up for a 50 minute session with a Coach ($250) to make sure your plan is set up correctly. We also provide full service advice from a CFP® professional at Boldin Advisors.