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Free tool · For pre-retirees & retirees

The Retirement Tax Leak Audit

Built for people within about five years of drawing retirement income, or already there. These twelve questions identify potential tax leaks in your plan. Not there yet? Answer the way you'd expect to if you needed retirement income today.

This is an educational self-check, not personalized advice. Your answers stay on your device: nothing is stored or sent anywhere.

0 of 12 answered

Section 1: Income Sources & Withdrawal Order

1) Do you have a clear plan for the order in which you'll draw from your retirement accounts (401(k), IRA, Roth, brokerage)?

2) Which accounts do you typically withdraw from first?

3) Have you evaluated whether taking some income earlier in retirement, before Social Security or RMDs begin, could reduce your lifetime tax burden?

Section 2: Social Security Timing & Tax Interaction

4) Have you analyzed how the timing of your Social Security benefits affects how those benefits are taxed?

5) Do you know what percentage of your Social Security benefits will be taxable, based on your combined income?

Section 3: Roth Conversion Opportunities

6) Have you explored whether converting some traditional IRA or 401(k) funds to a Roth IRA could save you money in the long run?

7) Are you aware of the "tax bracket gap": years when your income is lower (for example, between retirement and Social Security or RMDs) that create a window for low-cost Roth conversions?

Section 4: RMD Readiness & Tax Exposure

8) Do you have a plan to manage Required Minimum Distributions (RMDs) so they don't push you into a higher tax bracket?

9) Have you calculated how your RMDs, combined with other income, could affect your Medicare premiums through IRMAA surcharges?

Section 5: Capital Gains & Portfolio Tax Efficiency

10) Are you strategically managing capital gains in your taxable investment accounts, for example, harvesting losses or timing sales to stay in lower brackets?

11) Is your portfolio structured with tax efficiency in mind, for example, holding tax-inefficient assets (bonds, REITs) in tax-advantaged accounts?

Section 6: Overall Tax Planning

12) Do you work with a financial advisor or tax professional who creates a multi-year tax projection for your retirement?