Free tool · For pre-retirees & retirees

The Retirement Tax Leak Audit

Twelve questions that show where taxes may be quietly draining your retirement income, and what to focus on first. Built for people within about five years of drawing retirement income, or already there. 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 unless you choose to email yourself a copy at the end.

0 of 12 answered

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?

Yes, I've optimized my claiming strategy with taxes in mind

I know timing matters but haven't done a detailed analysis

I plan to claim based on age preference, not tax impact

I didn't know Social Security timing affected my taxes

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

Yes, and I'm managing other income to minimize the taxable portion

I know some of it is taxable but not the exact percentage

I assume most or all of it will be taxed

I didn't know Social Security benefits could be taxed

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?

Yes, I do strategic Roth conversions based on tax-bracket analysis

I've looked into it but haven't pulled the trigger

I've heard about Roth conversions but don't understand the benefit

No, I haven't considered this

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?

Yes, I'm actively using this window for conversions

I've heard about this but haven't acted on it

I'm not sure when my income will be lower

This is the first I'm hearing about it

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?

Yes, I've been proactively reducing my pre-tax balance before RMDs start

I know RMDs are coming but haven't planned for the tax impact

I'll deal with RMDs when I have to

I'm not sure what RMDs are or when they start

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

Yes, I factor IRMAA thresholds into my withdrawal planning

I know higher income can increase Medicare costs but haven't planned for it

I've heard of IRMAA but don't know how it applies to me

I didn't know retirement income could affect Medicare premiums

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?

Yes, I actively manage gains and losses for tax efficiency

I try to be mindful but don't have a formal strategy

I sell investments when I need the money, without considering tax impact

I haven't thought about capital gains management

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

Yes, my portfolio uses asset-location strategies

I have some awareness but haven't optimized placement

My investments are spread around without much thought to tax efficiency

I'm not sure what asset location means

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?

Yes, I have a comprehensive, forward-looking tax plan reviewed annually

My advisor addresses taxes, but we don't do multi-year projections

I rely on my tax preparer at filing time but don't plan ahead

I don't currently work with anyone on retirement tax planning

One check most people forget

A beneficiary designation overrides your will, and it's easy to lose track of. The Beneficiary Check-In is a free five-minute worksheet to review yours, account by account.

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