tax-efficient-withdrawal-sequencing — tax strategy and optimization

Why Withdrawal Order Determines Retirement Tax Burden

The sequence in which you tap different account types can save $100,000 to $300,000 in lifetime taxes for retirees with $1 million+ portfolios (Kitces & Pfau, 2016). Most retirees follow the conventional wisdom of "taxable first, tax-deferred second, Roth last." This approach works reasonably well but leaves significant tax savings on the table compared to dynamic strategies that manage bracket utilization each year.

The central problem: Traditional 401(k) and IRA accounts grow tax-deferred but eventually face required minimum distributions (RMDs) starting at age 73. If these accounts grow too large, RMDs push retirees into higher tax brackets. Strategic withdrawals before RMDs begin can smooth taxable income across retirement years and reduce total taxes paid.

The Three Withdrawal Sources

Taxable Brokerage Accounts

Withdrawals from taxable accounts generate varying tax consequences depending on what you sell:

Long-term capital gains: Taxed at 0%, 15%, or 20% depending on income
Short-term capital gains: Taxed as ordinary income
Return of cost basis: No tax (you already paid tax on contributions)
Qualified dividends: Taxed at 0%, 15%, or 20%

For 2024, the 0% long-term capital gains rate applies to taxable income up to $47,025 (single) or $94,050 (married filing jointly). This means retirees with low ordinary income can realize gains tax-free.

Tax-Deferred Accounts (Traditional 401(k), IRA)

Every dollar withdrawn is taxed as ordinary income at your marginal rate (10%, 12%, 22%, 24%, 32%, 35%, or 37%).

Required minimum distributions (RMDs):

Begin at age 73 (SECURE 2.0 Act)
Calculated using IRS Uniform Lifetime Table
Approximately 3.7% of balance at age 73, increasing each year
Failure to take RMDs triggers 25% excise tax on the amount not withdrawn

A $1 million Traditional IRA at age 73 requires approximately $37,000 in first-year RMDs, creating $37,000 in taxable income regardless of other needs.

Roth Accounts (Roth IRA, Roth 401(k))

Qualified withdrawals are completely tax-free. No RMDs during the owner's lifetime (Roth 401(k) RMDs were eliminated in SECURE 2.0). Roth accounts also transfer tax-free to beneficiaries.

Qualification requirements:

Account owner is 59.5 or older
Account has been open for at least 5 years
Contributions can be withdrawn tax-free at any time (basis already taxed)

The Conventional Approach: Taxable, Tax-Deferred, Then Roth

The traditional sequence:

Years 1-X: Spend taxable accounts first
Years X-Y: Spend tax-deferred accounts after taxable is exhausted
Years Y-End: Spend Roth accounts last

Why it works: Each year's withdrawals are taxed only once. Taxable accounts generate minimal tax if gains are harvested at low rates. Tax-deferred accounts benefit from additional years of untaxed growth. Roth accounts grow tax-free longest.

Why it's suboptimal: This approach ignores bracket management. A retiree might withdraw from tax-deferred accounts at 12% in early retirement years, then face 22% or 24% rates when RMDs force larger distributions.

The Optimal Approach: Bracket-Filling Strategy

The tax-efficient strategy fills lower tax brackets deliberately in early retirement to reduce future RMD-driven income:

Phase 1 (Age 62-72): Fill brackets with strategic withdrawals

Withdraw from taxable accounts for living expenses
Simultaneously convert Traditional IRA to Roth IRA up to the top of your current bracket
Goal: Reduce Traditional IRA balance before RMDs begin

Phase 2 (Age 73+): Manage RMDs while preserving Roth

Take required RMDs (no choice)
Supplement with taxable account withdrawals if available
Use Roth only when lower-tax sources are exhausted

Phase 3 (Late retirement): Spend Roth for maximum flexibility

Roth withdrawals don't affect Medicare premium brackets (IRMAA)
Roth withdrawals don't increase taxation of Social Security benefits
Roth provides tax-free cushion for unexpected expenses

Worked Example: Optimal Sequencing for a Retiree Couple

Starting situation at age 65:

Taxable brokerage: $400,000
Traditional 401(k): $1,200,000
Roth IRA: $200,000
Annual spending need: $80,000
Social Security (starting at 67): $40,000 combined
Filing status: Married filing jointly

Years 65-66 (Before Social Security)

No Social Security income yet. Use this window for aggressive Roth conversions.

Annual strategy:

Withdraw $80,000 from taxable for living expenses (assume $60,000 basis, $20,000 gain)
Tax on $20,000 long-term gain at 0% rate: $0 (income below $94,050 threshold)
Convert $94,050 from Traditional IRA to Roth IRA
Tax on conversion: $10,852 (10% on $23,200 + 12% on $70,850)

Two-year result:

Taxable account: $400,000 - $160,000 = $240,000
Traditional IRA: $1,200,000 - $188,100 conversions = $1,011,900
Roth IRA: $200,000 + $188,100 conversions = $388,100
Taxes paid on conversions: $21,704

Years 67-72 (Social Security, Pre-RMD)

Social Security creates $40,000 annual income (up to 85% taxable at higher incomes).

Annual strategy:

Social Security: $40,000 (approximately $34,000 taxable at this income level)
Withdraw $40,000 from taxable for remaining spending needs
Convert $60,000 from Traditional IRA to Roth (filling 22% bracket)
Tax on conversion: approximately $12,800 annually

Six-year result:

Taxable account: $240,000 - $240,000 = $0
Traditional IRA: $1,011,900 - $360,000 conversions + growth = ~$850,000
Roth IRA: $388,100 + $360,000 conversions + growth = ~$950,000
Additional taxes paid: $76,800

Years 73+ (RMD Phase)

RMDs now required on Traditional IRA balance of approximately $850,000.

Year 73 RMD calculation:

Balance: $850,000
Distribution period (age 73): 26.5 years
Required distribution: $850,000 / 26.5 = $32,075

Compare to non-optimized scenario:

Traditional IRA without conversions: ~$1,600,000 at age 73
Required distribution: $1,600,000 / 26.5 = $60,377

Annual tax savings in RMD phase:

Optimized RMD: $32,075 at 12% bracket = $3,849 tax
Non-optimized RMD: $60,377 at 22% bracket = $13,283 tax
Annual savings: $9,434

Over 20 years of RMDs, bracket management saves approximately $188,680 in taxes. Net of the $98,504 paid during conversion phase, lifetime savings exceed $90,000.

Key Factors That Affect Optimal Sequencing

Social Security Taxation

Social Security benefits become up to 85% taxable when combined income exceeds $44,000 (married filing jointly). Every dollar of Traditional IRA withdrawal can trigger additional Social Security taxation.

Impact: A $1,000 withdrawal from a Traditional IRA can create $1,850 in taxable income ($1,000 withdrawal + $850 Social Security now taxable). This effective 85% "bonus taxation" makes Roth conversions before Social Security begins particularly valuable.

Medicare Premium Brackets (IRMAA)

Income above certain thresholds triggers Income-Related Monthly Adjustment Amounts (IRMAA) for Medicare Parts B and D.

2024 IRMAA thresholds (married filing jointly):

$206,000 or less: Standard premium
$206,001-$258,000: +$66.00/month per person
$258,001-$322,000: +$164.80/month per person
Above $750,000: +$395.60/month per person

Roth withdrawals do not count toward IRMAA calculations. Converting to Roth before Medicare eligibility (age 65) reduces future IRMAA exposure.

State Tax Considerations

Some states fully tax retirement distributions; others offer partial or complete exemptions:

No state income tax: Texas, Florida, Nevada, Washington, Wyoming, Alaska, South Dakota, Tennessee, New Hampshire
Exempt Social Security: Most states
Exempt pension/retirement income: Several states offer partial exclusions

If you plan to relocate to a no-income-tax state, delaying Traditional IRA withdrawals until after the move saves state taxes on distributions.

Common Pitfalls in Withdrawal Sequencing

Pitfall 1: Ignoring the Gap Years

The period between retirement and RMDs (typically ages 62-72) offers the best opportunity for low-bracket Roth conversions. Retirees who simply spend taxable accounts without converting miss this window.

The cost: Each $10,000 not converted during 12% bracket years will eventually be distributed at 22% or higher, costing $1,000+ in additional taxes.

Pitfall 2: Over-Converting in a Single Year

Converting too much in one year pushes income into higher brackets and potentially triggers IRMAA penalties.

The rule: Calculate your current bracket ceiling and convert up to that limit, not beyond. For 2024, the 12% bracket ends at $94,300 for married filing jointly. Converting $150,000 in one year wastes bracket space and overpays taxes.

Pitfall 3: Spending Roth Too Early

Using Roth funds when taxable or tax-deferred sources are available wastes permanent tax-free growth.

Exception: Roth withdrawals may be preferable to avoid IRMAA brackets or to manage Social Security taxation in specific years.

Pitfall 4: Forgetting About Capital Gain Harvesting

Retirees with low taxable income can realize long-term capital gains at 0% while simultaneously doing Roth conversions, as long as combined income stays below thresholds.

Tax-Efficient Withdrawal Checklist

Annual planning (do each December):

Calculate next year's taxable income (Social Security, pensions, RMDs, other)
Identify remaining space in 12% or 22% bracket
Determine if Roth conversions make sense for bracket-filling
Check IRMAA thresholds two years ahead (Medicare uses two-year lookback)
Harvest capital gains at 0% rate if below threshold

Withdrawal priority order:

Take required RMDs first (mandatory, no flexibility)
Spend taxable account funds for living expenses
Fill remaining bracket space with Roth conversions
Use Roth only when lower-tax sources exhausted or for IRMAA management

Long-term strategy:

Project Traditional IRA balance at age 73
Calculate expected RMDs at that balance
Determine if RMDs will push you into higher brackets
If yes, increase conversion activity in remaining pre-RMD years

Records to maintain:

Roth IRA contribution and conversion history (for 5-year rules)
Cost basis in taxable accounts (for gain calculations)
Annual tax returns showing conversion amounts
Documentation of bracket-filling decisions

Withdrawal sequencing is not a one-time decision. Each year requires evaluation of income projections, bracket boundaries, and account balances. The retirees who save the most are those who actively manage their tax liability across all retirement years rather than following a fixed formula.

Tax-Efficient Withdrawal Sequencing