Map the timeline
Organize the final paycheck, Social Security, Medicare and RMD milestones.
Free retirement tax-planning guide
Understand the Retirement Tax Window Before You Act.
The years between your final paycheck, Social Security, Medicare and later RMD years can create a different income profile. The guide helps organize the questions without assuming a Roth conversion or other strategy is automatically beneficial.
Get the resource
The Retirement Tax Window Guide
Understand interactions
Identify how withdrawals, conversions and gains can affect taxable income and income-sensitive programs.
Model before acting
Use current and projected years rather than assuming a conversion or withdrawal automatically lowers lifetime tax.
Who it's for
For people with meaningful pre-tax retirement savings and a few years before RMDs.
- You expect a gap between your last paycheck and the start of Social Security or RMDs.
- You have heard about Roth conversions but want to understand the trade-offs first.
- You will use Marketplace coverage before 65, or you are close to the Medicare IRMAA thresholds.
- You want an organized set of questions for your tax professional.
What's inside
A year-by-year planner that lists every threshold, not just your bracket.
- What creates a tax window, and why lower income in one year does not automatically mean lower lifetime taxes.
- Key milestones: the final paycheck, Marketplace years, the age-63 IRMAA look-back, 65, Social Security, RMDs at 73 or 75, and the survivor's filing status.
- 2026 reference figures: standard and senior deductions, bracket thresholds, the 0% capital-gain range, IRMAA and Social Security taxation thresholds.
- Worksheet 1, the year-by-year planner, plus a labeled hypothetical row showing how a Marketplace threshold can matter more than the tax bracket.
- Roth conversion facts: taxation, no recharacterization, five-year periods and MAGI effects.
- A timeline checklist, questions for your tax professional and common mistakes.
Sample checklist items
- Estimate MAGI for the Marketplace (if under 65) and for IRMAA two years ahead.
- Review whether partial Roth conversions or gain harvesting fit. Conversions must be completed by December 31.
- Keep records of IRA basis (Form 8606) and conversion dates.
- Project your first RMDs from current traditional balances.
- Consider how a survivor's single filing status would change the picture.
Selected 2026 figures in the guide
| Item | Single | Married filing jointly |
|---|---|---|
| Standard deduction | $16,100 | $32,200 |
| Top of the 12% bracket (taxable income) | $50,400 | $100,800 |
| 0% long-term capital-gain rate up to (taxable income) | $49,450 | $98,900 |
| Senior deduction, age 65+ (2025–2028), before phase-out | $6,000 | $6,000 per eligible spouse |
Sources: IRS 2026 inflation adjustments; IRS enhanced deduction for seniors. Educational only; not tax or legal advice.
Prefer to read first? See the retirement tax window and Roth conversions in the retirement window.
Education first
Use the resource to organize the questions before you act.
The guide does not assume a Roth conversion or any other strategy is right for you. Individual recommendations require individual facts and an appropriate advisory process.