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Free retirement tax optimizer · by Frank Finly

Retirement Tax Optimizer — Free Roth Conversion & Withdrawal Strategy Calculator

Americans overpay an average of $6,000–$12,000/year in retirement taxes they didn’t have to pay. Find the specific strategies — Roth conversion timing, Social Security tax optimization, withdrawal sequencing, RMD planning — that apply to your retirement accounts, age, and state.

Find My Tax Savings→

Free. 11 questions. 3 minutes. Email only to unlock your playbook.

How do I optimize taxes in retirement?

Five strategies reliably reduce retirement taxes for most Americans: (1) Roth conversions in low-income years before RMDs start at age 73, (2) tax-efficient withdrawal sequencing (taxable accounts first, Roth last), (3) state residency planning (0% vs. up to 13.3% income tax), (4) Qualified Charitable Distributions after 70½, and (5) IRMAA bracket management to avoid Medicare surcharges. Frank Finly’s tax optimizer identifies the ones that fit your situation, ranked by estimated annual savings.

If this is you

You’re leaving money on the table.

The tax drag you can feel but can’t name. If any of this feels familiar, keep reading.

““I’m getting hit from every direction.””

Pension, Social Security, rental income, RMDs, dividends, maybe a part-time job. Each one changes your bracket. You can’t tell which lever to pull.

““Does Roth conversion apply to me?””

Generic articles say “Roth conversions save taxes.” Okay. How much? In which year? Before or after Social Security? For you, in your state, at your income — that’s the real question.

““Nobody tells me what I should’ve done.””

TurboTax and CPAs are backward-looking. They clean up the past. They don’t optimize the future.

“The jargon wall.”

Roth, pro-rata, IRMAA, NIIT — the acronyms alone make brains shut down. You need one number: “convert $X this year, save $Y across 10 years.”

“The timing trade-off.”

Most advice asks you to sacrifice today for abstract gains decades out. You want strategies that save money this year — present-you and future-you on the same team.

What you walk away with

Personalized strategies. Real trade-offs.

Not generic tips — real strategies matched to your retirement accounts, age, and timeline.

Roth conversion window.

The years before RMDs start are your golden window — see if you’re using it and how much to convert per year.

Avoid tax surprises.

Social Security taxation, IRMAA surcharges, RMD bracket spikes — see what’s coming before it hits.

Dollar amounts, not vague tips.

Every strategy shows estimated annual savings in real dollars (as a range, not a false-precision single number).

Decision branches.

“Roth now vs. later” shown side-by-side with trade-offs spelled out. You decide.

““I think I’m overpaying but I can’t prove it.””

“My effective rate is 28%. Top 3 moves save an estimated $10K–$18K/yr.”

What the dashboard actually gives you

  • Retirement tax rate projection — current trajectory vs optimized, including RMD impact
  • Top 3 strategies ranked by estimated $-savings with confidence indicators
  • Full playbook of all applicable retirement tax strategies
  • Decision branches where two strategies conflict (Roth aggressive vs gradual, SS early vs delay)
  • Golden window analysis — years between retirement and RMDs mapped to Roth conversion opportunity
How it works

Three steps. Three minutes.

Answer 11 quick questions.

Retirement accounts, pre-tax/Roth balance, Social Security plans, retirement status, filing status, state, age. 3 minutes.

01

See your retirement tax picture.

Projected retirement tax rate (current trajectory vs optimized). Top 3 strategies ranked by estimated annual savings.

02

Decide or delegate.

Each strategy includes how-to guidance. DIY, or connect with an advisor who specializes in your situation.

03

Your numbers in, your strategies out. The decisions stay yours.

Here is what you’ll see.

Sample based on a 62-year-old with $800K Traditional IRA, $40K pension, SS at 67, CA resident. Your situation will produce your own playbook.

Effective rate28% → could be lower
Roth conversion$4K–$8K/yr savings
CA → FL relocation$6K–$12K/yr savings
Decision branches2 open
Golden windowAges 63–66
Playbook5 strategies ranked
Side by side

What changes after 3 minutes.

The shift from guessing to knowing.

Overpaying?01
Traditional

“I think I’m overpaying but I can’t prove it.”

Frank Finly

“My effective rate is 28%. Top 3 moves save $10K–$18K/yr.”

Roth conversion02
Traditional

“Sounds good — does it apply to me?”

Frank Finly

“Convert in years 63–66, save $4K–$8K/yr. After SS, the math flips.”

Relocating?03
Traditional

“Should I move to Florida?”

Frank Finly

“CA → FL saves ~$9K/yr. Break-even on moving costs: 14 months.”

Strategy04
Traditional

“My CPA files my return. I’m guessing on strategy.”

Frank Finly

“I’ve seen the full playbook. I can hire an advisor with a real brief.”

Forward-looking?05
Traditional

TurboTax/CPA handles last year’s return.

Frank Finly

Identifies strategies to implement this year and across the Roth window.

The optimizer is free

You never owe Frank Finly anything. The tax optimizer, the playbook, the strategies — yours to keep.

01

Advisors pay for introductions

If you want a person to walk through it, advisors in our network pay Frank Finly for the introduction — only when you ask. Advisors may charge their own fees for their services.

02

Bank-level encryption

Your financial data is encrypted in transit and at rest. We don’t sell it unless you ask to talk to an advisor.

03
How the money works

What’s the catch? None.

The dashboard is free for you. Advisors in our network pay Frank Finly for introductions — only when you ask for one. You never owe us anything.

Why trust our analysis

Built by professionals. Not by marketers.

15+ years of retirement & tax planning expertise. Federal tax brackets, state rates, FICA, Medicare surtax, NIIT, IRMAA — all the hidden taxes, modeled. Pension + SS + rental + RMD + dividends + part-time work — integrated. That’s where the real optimization lives.

— How the optimizer works

IRS-accurate calculations.

Federal tax brackets, state rates, FICA, Medicare surtax, NIIT, IRMAA. All the hidden taxes, modeled.

Ranges, not false precision.

Tax optimization depends on future variables. We show honest ranges and flag uncertainty.

Your data is yours.

It stays with Frank Finly to run your optimizer. Nothing goes to any firm unless you ask to talk to an advisor. Opt out at any time on our Do Not Sell or Share page.

Sample tax picture

Current effective rate28%
Top strategyRoth conversion
Estimated savings$4K–$8K/yr

Illustrative example — your numbers produce your own playbook

Roth conversion timing explained →
Insights

Tax strategies explained. Not complicated.

Deep-dive articles from our tax planning team.

Roth Conversion Timing for 2026

Roth Conversion Timing for 2026

→

When to convert — and when to wait. The decision framework for this year.

RMD Calculator

RMD Calculator

→

Understand your required withdrawals and plan your tax strategy.

State Tax in Retirement

State Tax in Retirement

→

How CA, NY, IL retirees actually save by relocating — and when the math breaks down.

Retirement Tax Traps

Retirement Tax Traps

→

Why your Traditional IRA is a time-bomb at 73 — and the 10-year window to fix it.

View all articles→
Common questions

Questions? Answers.

The short answer: you can’t do it completely tax-free, but you can minimize the bill. Three main strategies: (1) convert in low-income years — gap years between retirement and age 73 when RMDs start, (2) convert amounts that stay within your current bracket, and (3) use the pro-rata rule awareness if you have after-tax contributions. For most pre-retirees, the “Roth conversion window” between retirement and age 73 is worth $50K–$200K+ in lifetime tax savings.
A Roth conversion moves money from a pre-tax account (Traditional IRA or 401(k)) to a Roth account. You pay income tax on the converted amount now, in exchange for tax-free growth and withdrawals later. It makes sense when your current tax bracket is lower than your expected retirement bracket, when you have a large Traditional IRA at risk of the “RMD tax bomb” at 73, or when you want tax diversification in retirement.
The pro-rata rule says that if you have both pre-tax and after-tax money in your Traditional IRAs, any conversion is proportionally treated as pre-tax and after-tax. This complicates the “backdoor Roth” strategy for high earners. If you have no after-tax Traditional IRA money, pro-rata doesn’t affect you. The optimizer flags this based on your account types.
IRMAA adds up to $5,000+/year in Medicare Part B & D premiums once your income crosses thresholds (~$103K single / $206K married in 2026). Keep your MAGI below the threshold in years you’ll be on Medicare (65+). Key tactics: spread Roth conversions across multiple years, use QCDs after 70½ to reduce AGI, harvest gains strategically.
Yes. The tax optimizer and full playbook are free. Frank Finly is paid by the advisors we match users with — you never are.
Because tax optimization depends on future unknowns: tax law changes, your actual income, life events. We show honest ranges and flag uncertainty. Calculators that give you one exact number are either lying or ignoring reality.
TurboTax and CPAs are backward-looking — they handle last year’s return. The Retirement Tax Optimizer is forward-looking — it identifies retirement tax strategies to implement this year and across the Roth conversion window. Bring the playbook to your CPA; it makes the conversation 10× more productive.
Yes. We model all 50 states, including the 9 states with no income tax on retirement income (FL, TX, NV, WY, SD, WA, AK, TN, NH). Relocation analysis included.
Yes. At 73, RMDs force taxable withdrawals whether you need the money or not. If your balance is large, RMDs can push you into a higher bracket and trigger IRMAA. The Roth conversion window before 73 is the key fix — the optimizer shows you if it applies and how much to convert per year.
Some will. That’s why we have decision branches — “Option A vs Option B” with the trade-offs spelled out. You decide based on your priorities, or ask an advisor.
Only if you ask to talk to an advisor. When you submit your contact details, Frank Finly sells your answers and contact details to one financial advisory firm, so an advisor there can contact you — that is how the tool stays free. You can opt out at any time on our Do Not Sell or Share My Personal Information page.
Your next step

Stop paying tax you don’t have to.

11 questions. 3 minutes. Frank Finly’s free retirement tax optimizer — with Roth conversion, Social Security, withdrawal sequencing, and RMD strategies ranked by estimated annual savings.

Find My Tax Savings→