Guide
The Retirement Tax Playbook
How to minimize taxes on your retirement income and avoid costly tax traps.
Every dollar in your traditional IRA or 401(k) carries an unpaid tax bill, and the order you withdraw from your accounts determines how large that bill ends up being. This guide covers withdrawal sequencing, Roth conversions, RMDs, IRMAA, capital gains, and Social Security taxation, using the actual 2026 numbers, for households with $1.5M+ in investable assets working through the years between retirement and Required Minimum Distributions.
18 pages. 6 charts. A fillable worksheet. No commitment, no sales agenda.
$180,000+
Illustrative 20-year tax difference between conventional and managed withdrawal order
84%
Of retirees at RMD age withdraw only the legal minimum, per EBRI and J.P. Morgan research
$6,936
Top-tier annual Medicare IRMAA surcharge per person for 2026, on top of standard premiums
What's inside
How your federal bracket, Social Security taxation, and Medicare IRMAA each run on a different income test, and how they interact
The 2026 federal brackets, long-term capital gains brackets, and IRMAA tiers, each with primary-source citations
Why the Social Security taxation thresholds have not moved since 1993 while the average benefit has roughly tripled
A full worked example: two withdrawal paths for the same household, twenty years apart, side by side
What changes the year the first spouse dies, and why the joint-filing years are your only window to hedge it
The four specific, named ways retirees blow up their own tax plan, and what prevents each one
A four-question decision framework you run every year, not once at retirement
A nine-step action plan with an owner, a deadline, and the document you need for each step
A fillable worksheet to run your own numbers before your next tax-planning conversation
The four ways this goes wrong
Not hypothetical risks. Each one shows up repeatedly in real retiree tax returns, and each one is preventable. The full guide covers who each one hits, what it costs, and exactly how to prevent it.
The RMD Bomb
Waiting until 73 to think about your pre-tax balance lets it compound, uninterrupted, until a forced withdrawal stacks on top of Social Security and pushes you from a comfortable 22% bracket into 32% or higher.
The IRMAA Surprise
A single large income event, two years before you expect it because of the Medicare lookback, trips a surcharge tier you never modeled and cannot undo after the fact.
The Static Threshold Trap
The Social Security taxation thresholds haven't moved since 1993. Your benefit grows with COLA every year. A growing share of ordinary retirees cross the 85%-taxable line without realizing it.
The Minimum-Only Mistake
Treating the RMD as the withdrawal plan rather than a floor lets the balance keep compounding at an ever-larger, ever-more-taxable size, then transfers the bill to heirs on an accelerated 10-year clock.
Frequently Asked Questions
What is the single biggest tax mistake retirees make with withdrawals?
Letting a pre-tax IRA or 401(k) compound untouched until Required Minimum Distributions begin at 73 or 75. The forced withdrawal is calculated off a larger balance than if you had drawn it down gradually, and it stacks on top of Social Security and any pension, often pushing a household that felt comfortable in the 22% bracket into 32% or higher. The years between when your paycheck stops and RMDs begin are the cheapest tax years available, and most retirees let them pass without acting.
How much of my Social Security benefit is taxable in 2026?
Up to 85%, depending on your combined income (adjusted gross income plus half your Social Security benefit plus any tax-exempt interest). For married couples filing jointly, up to 50% becomes taxable above $32,000 of combined income, and up to 85% becomes taxable above $44,000. Those thresholds were set by statute in 1983 and 1993 and have never been indexed for inflation, so a growing share of retirees cross them every year as benefits rise with the annual COLA.
What triggers an IRMAA surcharge, and how much does it cost?
Medicare Part B and Part D premiums are set by your Modified AGI from two years earlier, so your 2026 premium is based on your 2024 tax return. Crossing an IRMAA income tier by even one dollar triggers the entire tier's surcharge for a full year, not a prorated amount. For 2026, the five tiers add between $1,148 and $6,936 per person per year on top of the standard premium, for married couples filing jointly with MAGI above $218,000.
What happens to our tax bracket when one spouse dies?
It usually gets worse, on the same income. The surviving spouse files as single the following year, with roughly the same pre-tax balance and RMD schedule but a standard deduction and bracket thresholds close to half the married amounts, and an IRMAA threshold that is exactly half. A household comfortably in the 22% bracket as a couple can land at 24% or 32% as a survivor, on income that did not change. The main hedge is converting more than feels comfortable to Roth while both spouses are alive and filing jointly, since that window closes the moment the first spouse passes.
Related Resources
Want this run against your actual numbers?
The guide is the framework. Your specific balances, brackets, Social Security claiming dates, and IRMAA exposure determine the strategy. Singh PWM is a flat-fee CFP® and Enrolled Agent practice serving Arizona pre-retirees and retirees on a fiduciary basis.
No commitment. No sales agenda. 30 minutes.