By David Park, Real Estate & Tax Correspondent

Introduction: What you'll learn and why this June 2026 update matters

This update gives you an immediate, year-specific action plan for coordinating Roth conversions, required minimum distributions (RMDs), Social Security timing, and housing events through the remainder of 2026 and into the next decade. If you’re in your 50s, 60s or already retired and managing traditional 401(k)/IRA balances, a Roth account, Medicare exposure, and potential home-sale proceeds, this article tells you exactly what to check this month, how to size conversions, and how to protect survivors.

Why this June 2026 checkpoint is useful: the planning inputs that matter—RMD rules under SECURE 2.0, MAGI-driven Medicare IRMAA lag, state-level tax changes, and the post-2025 federal-tax landscape—are settled enough to re-run your maps but still fluid enough that annual discipline matters. This piece adds fresh examples, updated sequencing guidance, and practical checks to use now.

Prerequisites / Context: What you need before you start

You don't need a huge spreadsheet. You do need the right numbers and the right checklist. Collect these items before you act.

Gather these documents and numbers

  • Latest account statements — traditional 401(k)/IRA and Roth balances, including employer-plan Roth balances and in-plan Roth options.
  • Pension paperwork — start dates, survivor options, and COLA assumptions.
  • Social Security estimates from SSA for earliest, FRA and age-70 claiming.
  • Last two tax returns (Form 1040) and a current year-to-date income snapshot.
  • Mortgage, property tax, and rental statements — housing events often drive one-year taxable spikes.
  • Medicare notices — Part B/D premium notices and any IRMAA determinations.

Key rules and reminders for mid‑2026

  • RMD starting age: SECURE 2.0 set the standard RMD age at 73 for cohorts affected today. That means many retirees will start required withdrawals at 73—still a material planning horizon.
  • Roth accounts: Roth IRAs remain tax-free for qualified withdrawals and are not subject to lifetime RMDs for original owners. Roth 401(k) balances can be subject to plan-level RMDs unless rolled to a Roth IRA—confirm your plan rules.
  • IRMAA timing: Medicare Part B/D surcharges are based on MAGI from two years prior. A conversion in 2026 can increase premiums in 2028. Always model that lag.
  • Tax brackets: Federal brackets and state tax rules can change; verify current IRS tables and your state’s retirement-tax treatment before sizing conversions.

Disclosure: This is educational. Use this framework and validate numbers with a tax advisor and your plan administrator.

Step 1: Build your 3-phase income timeline (the backbone of the map)

Map your retirement in three phases—this clarifies where conversion room exists and when taxable pressure will appear.

  1. Phase 1 — gap years: Years when you’ve retired or reduced work but haven’t yet started Social Security or a pension. These are prime Roth-conversion years because taxable income can be low.
  2. Phase 2 — stacking years: Years when Social Security and pensions start and stack with withdrawals. Conversion room typically shrinks here.
  3. Phase 3 — RMD years: Starting at 73 for most people in 2026, RMDs arrive and create a forced taxable-income floor that can push survivors into higher brackets later.

Concrete June 2026 example

Couple, ages 65 in 2026, married filing jointly. Use this as a template you can adapt.

  • $1.0M in traditional 401(k)/IRA
  • $250k in Roth IRAs
  • $200k in taxable brokerage (basis $120k)
  • Pension: $30,000/year starting at 67 (joint-and-survivor option reduces survivor benefit by 30%)
  • Social Security: combined $48,000/year if both delay to 70
  • Spending target: $75,000/year

Why this matters: If they delay Social Security to 70 and start pension at 67, ages 65–67 create a multi-year conversion window. Converting deliberately in those years can materially reduce future RMDs and leave tax-free Roth assets for the survivor.

Step 2: Estimate your “floor income” (pension + Social Security + fixed sources)

Floor income is the predictable income that fills the lower tax brackets in future years. Model it under multiple claim-age scenarios because your conversion capacity depends on it.

  1. Add pension at each possible start-age and include survivor reductions.
  2. Calculate Social Security under earliest, FRA and age-70 claims; estimate the taxable portion using the combined-income rules.
  3. Include recurring rental income, annuity payments, and likely part-time wages.

Build two floor scenarios: a lower-floor (delayed Social Security and pension) and a higher-floor (both claimed early). If your conversion plan is robust across both, it’s more likely to survive real-life changes.

Step 3: Choose a default withdrawal order (then customize)

A simple default prevents accidental overtaxation. My recommended starting order:

  1. Taxable brokerage — use for early spending and to harvest gains in low-rate years.
  2. Traditional 401(k)/IRA conversions/withdrawals — convert up to a chosen marginal-bracket ceiling during gap years.
  3. Roth IRA — preserve as long-term, tax-free reserves and for heirs.

When to break the rule: if you need to satisfy a large one-time expense (home sale, education gift), or if you face a sudden increase in RMDs, adapt the sequence to tax and cash needs.

Step 4: Identify your 2026–2030 Roth conversion window and size conversions

Use a disciplined sizing rule rather than one large conversion.

  1. Pick a marginal-bracket ceiling you will not exceed in a conversion year (for example, the top of the 12% or 22% bracket). Document it.
  2. Estimate non-conversion taxable income for the year, including taxable Social Security, pension and expected realized gains.
  3. Convert only the space under that ceiling — i.e., Conversion = Bracket ceiling − Non-conversion taxable income − Standard/itemized deduction.
  4. Pay conversion taxes from outside retirement accounts when possible to preserve compounding in the Roth.
  5. Repeat annually and adjust if markets, income or law changes.

Example: If their projected non-conversion taxable income is $60,000 and they target staying under a $120,000 ceiling for married filing jointly, they could convert roughly $60,000 (adjusted for deductions and state tax). Converting $60k in 2026 might cost $13k–$18k in federal tax depending on bracket mix—paying that from taxable brokerage preserves the IRA principal growth.

Step 5: Coordinate Social Security with the tax map

Social Security timing is both a longevity and tax tool. Run multi-year cash-flow scenarios rather than relying only on breakeven charts.

  1. Model claiming at earliest, at FRA and at 70, then simulate RMDs and conversion plans across ages 65–85.
  2. Compare after-tax income pathways and survivor benefits; delaying increases survivor benefits and can change long-term tax exposure.
  3. Consider the interaction with Medicare IRMAA: delaying Social Security increases benefit amounts but may also increase MAGI through higher taxable Social Security in stacking years.

Practical balance: delaying Social Security typically widens conversion windows but increases the near-term need for portfolio withdrawals. Choose a mix that preserves conversion room while protecting portfolio longevity—often a partial delay or staged claiming gives the best balance.

Step 6: Plan for RMD years now—before they plan for you

RMDs arrive at 73 and can compress lifetime taxation if the majority of your net worth is tax-deferred.

  • Ask: will pension + Social Security + RMDs push you into the top marginal brackets in your 70s and 80s?
  • Toolbox: staged Roth conversions in gap years, qualified charitable distributions (QCDs) once eligible (age 70½ or the current qualifying age), and in-plan Roth rollovers when plan rules allow.
  • Tip: Rolling Roth 401(k) balances to Roth IRAs before RMDs can avoid plan-level RMDs—confirm whether your plan permits in-service rollovers and whether state tax treatment changes the calculus.

Step 7: Pressure‑test for housing and family what‑ifs

Large housing events and family transfers are common plan breakers. Test them now.

Sale of a primary residence

An expected sale can create a high-income year. Even with the primary-residence exclusion, large taxable gains or substantial reinvestments can affect MAGI. Coordinate sale timing with conversion plans—avoid stacking big taxable events in one year.

Survivor outcome

Model the survivor as a single filer. Survivors often inherit a higher effective tax burden. Prioritize building Roth capacity for the survivor to afford more predictable, lower-tax cash flow.

Gifting and family support

Planned large gifts (education, down payments) are often best funded from taxable or Roth accounts rather than from IRA withdrawals that could spike AGI, trigger IRMAA increases, or increase taxable Social Security.

Common mistakes that still derail plans in 2026

  • Claiming Social Security without re-running the conversion window and IRMAA effects.
  • Converting too aggressively in a single year and triggering higher Medicare premiums that persist.
  • Failing to check plan-level Roth rules—many sponsors introduced in-plan Roth options since SECURE 2.0, but availability and timing vary.
  • Neglecting the survivor tax picture—treat post-death cash flow for the surviving spouse as a core planning objective.

Pro tips — a decade-by-decade mindset

  • Document a conversion ceiling. Write it down (e.g., “Do not convert enough in any year to exceed the top of the 22% bracket”) and revisit annually.
  • Pay conversion tax from outside retirement funds. It’s a drag to pull taxes from the converted IRA—paying from taxable brokerage or cash preserves Roth growth.
  • Build a Roth inheritance reserve. Even modest Roth balances—$100k–$300k—can give a survivor or heirs outsized flexibility and lower long-term tax drag.
  • Model IRMAA for every conversion above $25k. The MAGI cliff for Medicare can make a $25k conversion more costly than two $12.5k conversions split across years.
  • Re-run the map annually in June. Taxes, markets and family circumstances change—make June your planning check-in.

FAQ

What's the RMD starting age in 2026?

For most affected taxpayers, SECURE 2.0 sets the RMD starting age at 73. RMD timing can vary for different birth cohorts and certain employer-plan rules; confirm your exact cohort’s age with your advisor and the IRS.

Will a Roth conversion in 2026 increase my Medicare premiums?

Yes—Medicare Part B and D surcharges (IRMAA) are based on your MAGI from two years earlier. A sizable conversion in 2026 can therefore raise premiums beginning in 2028. Model IRMAA when sizing conversions; sometimes spreading conversions over multiple years is cheaper overall.

Should I rush conversions in 2026 because of past tax changes?

Not by default. 2026 is an appropriate year to re-run lifetime-bracket math because federal and state tax landscapes have stabilized after the 2025 transitions. The right move depends on your lifetime income path, survivor goals, and state taxes. Use bracket-disciplined, staged conversions rather than a one-off “rush.”

How should I think about rolling Roth 401(k) balances to Roth IRAs?

Rolling Roth 401(k) balances to a Roth IRA can avoid plan-level RMDs and simplify estate planning. Confirm plan rules, check for employer-imposed restrictions, and model whether state tax or creditor protections differ between your plan and IRAs before rolling.

How often should I revisit the retirement tax map?

Annually—preferably mid-year—and whenever you have a major life or financial change (job/retirement, home sale, large gift, or health event). Treat the map as a living cash-flow engineering exercise, not a one-time spreadsheet.

Sources and tools: SECURE 2.0 provisions, IRS distribution guidance, SSA calculators, and Medicare IRMAA rules. Before acting, confirm current-year tax-bracket thresholds, standard deductions and IRMAA thresholds with the IRS and SSA tools and validate state tax rules with a local advisor.

Final thought: Build the map with decades in mind. A steady program of bracket-wise Roth conversions during low-income gap years—coordinated with Social Security sequencing and housing timing—delivers outsized benefits for survivors and simplifies multi-generational wealth transfer. Do the work once every year and you’ll buy tax flexibility for the next 30 years.