Retirement Planning Checklist 2026

Retirement planning is a sequence problem — the same decisions made in the wrong order, or at the wrong time, produce dramatically different outcomes. This checklist organizes the key actions by timing, from 10 years before retirement through your RMD years. Checkboxes save in your browser. Every item links to the full guide or calculator.

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Phase 1 — 10+ Years Before Retirement (Roughly Ages 50–60)

Accumulation isn't over, but retirement-income decisions start now. The choices you make in this window — catch-up contributions, LTC insurance, beneficiary designations — compound over the next decade.

Max out catch-up contributions. At 50+, you can add $8,000 to a 401(k) on top of the $24,500 base — a total of $32,500 in 2026.¹ If you're ages 60–63, the SECURE 2.0 super catch-up allows $11,250 additional — total $35,750. IRA catch-up: $1,100 extra at 50+ (total $8,600 per person). Every dollar contributed now has a decade or more to compound. → Retirement readiness calculator
Check your Social Security earnings record. Create a my Social Security account at ssa.gov and review every year of earnings. Errors take months to correct. Confirm your full retirement age (FRA is 67 for those born 1960+) and review your projected benefit at 62, 67, and 70. → SS claiming calculator
Evaluate long-term care insurance. Late 50s is the pricing sweet spot — premiums are lower, underwriting denial rates are lower. Roughly 70% of people 65+ will need some form of care. Waiting to 65 can double the premium; waiting to 70 may mean denial. Hybrid life/LTC policies are an alternative. → LTC planning guide
Open and fund an HSA if eligible. Triple-tax: deductible contributions, tax-free growth, tax-free qualified withdrawals for healthcare. 2026 limits: $4,400 self-only / $8,750 family + $1,000 catch-up if 55+.² You must stop contributing at Medicare enrollment (age 65). Every dollar in the HSA is healthcare inflation protection for retirement. → HSA in retirement guide
Stress-test your portfolio for sequence-of-returns risk. A 100% equity portfolio two years before retirement, hit by a bear market, can permanently derail a plan even if long-run averages are fine. Begin building a 2–3-year cash/short-bond buffer by age 60. → Sequence of returns stress-test calculator
Audit all beneficiary designations. 401(k)s, IRAs, and life insurance pass outside your will — to whoever you named, even if that was your ex-spouse in 1998. The SECURE Act changed inherited IRA rules substantially; old designations may no longer achieve their intent. Review every account. → Inherited IRA rules guide | → Estate planning guide
Calculate your retirement number. A starting-point formula: (annual spending − Social Security − pension) ÷ your withdrawal rate = target portfolio. The hard part is knowing your withdrawal rate, which depends on retirement age and spending flexibility. → Retirement number calculator | → Readiness score

Phase 2 — 2–4 Years Before Retirement (Ages ~61–64)

The window for locking in key decisions. Social Security strategy, healthcare coverage, Roth conversion timing, and estate-plan updates should all be settled before you hand in your resignation.

Model your Social Security claiming strategy. This is the single highest-leverage decision for most retirees — delaying from 62 to 70 increases the monthly benefit by 76%. For married couples, the higher earner's claiming age also sets the survivor benefit amount. Don't decide without running the math. → SS claiming strategies guide | → Breakeven calculator
Plan health insurance coverage for the gap to Medicare. If you retire before 65, you need a bridge. ACA marketplace, COBRA (up to 36 months for certain situations), or a spouse's employer plan are the main options. ACA subsidies phase out above 400% FPL — $60,240 for a single filer in 2026.³ Roth conversions affect ACA eligibility directly. → Early retirement health insurance guide
Start projecting Roth conversion amounts. Once earned income stops — and before RMDs begin at 73 or 75 — many retirees are in their lowest federal brackets since their 20s. Converting traditional IRA to Roth at 12–22% avoids paying 32–37% later when RMDs stack on top of Social Security. Model the right annual amount now. → Roth conversions guide | → Calculator
Choose a withdrawal strategy framework before day one. 4% rule, Guyton-Klinger guardrails, bucket strategy, floor-and-upside — each has different risk and spending-flexibility tradeoffs. Decide before you retire, not in the middle of a bear market. → Safe withdrawal rate guide | → Three-bucket strategy
Update your estate plan. Will, trust, durable power of attorney, and healthcare proxy should all be current. The OBBBA (July 2025) made the $15M estate/gift exemption permanent — any pre-2025 "sunset planning" designed to accelerate gifts may be obsolete.⁴ → Estate planning for retirees guide
Evaluate pension options if you have one. Lump sum vs. monthly payment: there is no universally right answer. The math depends on your health, your investment return assumption, and the value of the survivor benefit. The implied IRR of most pensions is meaningful. → Pension lump sum vs. monthly calculator
Decide your 401(k) rollover strategy. Roll to IRA for broader investment choices and Roth conversion flexibility — or keep in the plan if you're 55–59 and want the Rule of 55 penalty-free withdrawal option. If you hold company stock, evaluate NUA (net unrealized appreciation) strategy before rolling. → 401(k) rollover guide

Phase 3 — Year of Retirement

The administrative year. Medicare enrollment, Social Security application, tax payment setup, and HSA timing all have hard deadlines you cannot miss.

Enroll in Medicare on time. Your Initial Enrollment Period (IEP) opens 3 months before your 65th birthday and closes 3 months after. Missing it means waiting for the General Enrollment Period (January–March) and a permanent Part B premium penalty of 10% per 12-month period without creditable coverage.⁵ → Medicare enrollment guide
Choose Original Medicare vs. Medicare Advantage. This decision is harder to reverse than most people realize. Original Medicare + Medigap Plan G offers nationwide coverage and no prior authorization. Medicare Advantage typically has lower premiums but network restrictions and prior auth requirements that matter more at 80 than at 65. → Medicare guide | → Plan G vs. Plan N comparison
Establish your withdrawal order. Default hierarchy: taxable brokerage first (long-term gains taxed preferentially, step-up at death), traditional IRA next, Roth last — with tactical deviations for bracket management and IRMAA cliffs. Getting this right can save six figures over 25 years. → Tax-efficient withdrawal order guide
Apply for Social Security at the right time. SSA application processing takes 2–4 months. If you've decided on your claiming age, apply 3–4 months before you want benefits to begin. If you're delaying to 70, set a calendar reminder — benefits don't start automatically. → SS claiming strategies
Set up quarterly estimated tax payments. Without paycheck withholding, federal taxes on IRA withdrawals, Social Security income, pensions, and investment returns are your responsibility. Estimated payments are due April 15, June 15, September 15, and January 15. Underpayment penalties apply if you owe more than $1,000 at filing. → Tax minimization strategies
Stop HSA contributions at Medicare enrollment. Contributing to an HSA while enrolled in any part of Medicare triggers a 6% annual excise tax on excess contributions. Medicare Part A backdates enrollment 6 months for anyone 65+ who delays — stop HSA contributions at least 6 months before Medicare begins. → HSA in retirement guide

Phase 4 — First 5 Years of Retirement (Ages 65–70)

The "golden window." Earned income is gone. RMDs haven't started. For most retirees this is the lowest tax bracket they'll occupy for the rest of their lives — a narrow window for Roth conversions and 0% capital gains harvesting that closes once RMDs begin.

Execute Roth conversions aggressively each year. Model how much to convert annually to fill the 12% or 22% bracket — stopping short of the IRMAA Tier 1 cliff ($218,000 MAGI for MFJ in 2026).⁶ Converting $50–100K per year now avoids paying 32–37% on those same dollars when RMDs compound at 73. → Roth conversion calculator
Harvest capital gains at 0%. If your taxable income stays below $98,900 (MFJ) or $49,450 (single) in 2026, long-term capital gains are federally tax-free.⁷ This window — before RMDs inflate your income — is the opportunity to reset cost basis in your taxable brokerage account tax-free. Coordinate with Roth conversion amounts so neither pushes you over the 15% LTCG threshold. → Capital gains in retirement guide
Track IRMAA exposure every year. Medicare premiums two years out are based on your MAGI today. Staying below the $218,000 MFJ threshold saves roughly $1,750/year per couple in Part B surcharges alone. Roth conversions and capital gains both count toward MAGI. → IRMAA calculator | → Full retirement income tax estimator
Review the Social Security earnings test if working part-time. Collecting SS before FRA and earning above $24,480/year (2026) triggers a $1-for-$2 benefit reduction on excess earnings.⁸ Those withheld benefits are credited back at FRA — it's not permanently lost, just deferred — but the cash flow impact matters. → SS earnings test calculator
Watch the Social Security income tax torpedo. Up to 85% of your SS benefit is taxable once combined income (AGI + nontaxable interest + ½ of SS) exceeds $34,000 single / $44,000 MFJ.⁹ Roth conversions add to combined income; QCDs do not. Structuring income to stay below the torpedo threshold can save $3,000–$8,000/year in tax for a typical couple. → SS income tax calculator
Consider annuitizing a portion for a spending floor. A single premium immediate annuity (SPIA) converts a lump sum into guaranteed lifetime income. Covering baseline expenses with guaranteed income — SS + pension + SPIA — insulates discretionary spending from market volatility without requiring market timing. → Annuity guide and SPIA income estimator
Review Part D drug coverage every Open Enrollment. Medicare Advantage and Part D formularies change annually (Open Enrollment: October 15 – December 7). Your current plan's cost for your specific drugs can change substantially year-over-year. Spend 20 minutes on medicare.gov each fall comparing total annual drug cost — not just the premium. → Medicare Part D guide

The 8 decisions that move the needle most in retirement:

When to claim Social Security — can differ by $100,000+ in lifetime household benefits
How much to convert to Roth each year in the 60–73 window
Original Medicare + Medigap vs. Medicare Advantage at 65
Withdrawal order — taxable, traditional, Roth, and when to deviate
IRMAA management through annual income planning
Long-term care insurance — late 50s or early 60s is the window
Capital gains harvesting at 0% in the pre-RMD years
QCD strategy at 70½+ to reduce RMD tax and IRMAA exposure

A retirement income specialist models all 8 simultaneously — something spreadsheets rarely do well. See the complete tax minimization guide for how these strategies interact.

Phase 5 — Age 73+ RMD Years

Required minimum distributions change the tax math permanently. IRMAA, Social Security taxation, and bracket management all become harder once RMDs are stacked on top of SS income. QCDs become your primary tax lever.

Take your first RMD by April 1 of the year after you turn 73. You may delay the first RMD to April 1, but that stacks two RMDs into one tax year — potentially pushing you into a higher bracket and a higher IRMAA tier. Most planners recommend taking the first RMD in the year you turn 73 to spread the income. → RMD calculator with 15-year projection
Use QCDs to satisfy RMDs charitably. Once 70½, you can direct up to $111,000/year (2026, indexed)¹⁰ from your IRA directly to a qualified 501(c)(3). The distribution counts toward your RMD but is excluded from AGI — reducing Social Security taxation, lowering IRMAA exposure, and staying off your state income tax return in most states. → QCD guide and tax savings calculator
Aggregate RMDs correctly across account types. IRA RMDs can be aggregated — calculate the total across all IRAs and withdraw from whichever you choose. 401(k) RMDs cannot be aggregated — each plan requires a separate calculation and distribution. If you have both types, the rules apply differently. → RMD calculator
Review IRMAA exposure annually as RMDs grow. RMD income compounds over time as your balance shrinks more slowly than distributions grow in some scenarios. Rising RMDs pushing MAGI across IRMAA tiers can add $1,750–$3,500/year per couple in Medicare surcharges. Coordinate QCDs and any remaining Roth conversions to manage total MAGI. → IRMAA calculator
Update estate plan for post-SECURE Act inherited IRA rules. Most non-spouse beneficiaries now face a 10-year rule for inherited IRAs — with annual RMDs required during the 10-year period if the original owner was past their required beginning date, per T.D. 10001. Trust-as-beneficiary arrangements designed before 2020 may be counterproductive. → Inherited IRA rules guide | → Estate planning guide
Plan surviving-spouse income proactively. Social Security survivor benefits, inherited IRA rollover vs. separate-inherited-IRA choice, and the "widow's tax trap" (filing single at higher rates on the same income) are decisions that should be mapped out while both spouses are alive and clear-headed. The survivor typically needs a different portfolio structure than the joint household. → Couples retirement planning and SS coordination | → Survivor benefits guide

Get matched with a retirement income specialist

The checklist above is a framework. The hard part is running all of these decisions simultaneously for your specific numbers — your Social Security timing, your bracket trajectory, your IRMAA exposure, your healthcare costs, your legacy goals. That's what a fee-only retirement income specialist does: model the complete picture and tell you what actually moves the needle for your situation.

Get matched with a specialist

Related tools and guides

The Complete Retirement Income Planning Guide — stage-by-stage narrative guide to the full retirement arc
Retirement Income Tax Calculator 2026 — enter all income sources, see your complete federal tax picture
How to Minimize Taxes in Retirement: 7 Strategies — how withdrawal ordering, Roth conversions, QCDs, and IRMAA management interact
How to Choose a Financial Advisor for Retirement — credentials, fee structures, 10 questions to ask, red flags

Sources

IRS Notice 2025-67 — 2026 retirement plan contribution limits: 401(k) $24,500 base + $8,000 catch-up (age 50+); SECURE 2.0 § 109 super catch-up $11,250 (ages 60–63), total $35,750; IRA $7,500 base + $1,100 catch-up (age 50+). IRS retirement contribution limits
IRS Rev. Proc. 2025-19 — 2026 HSA contribution limits: $4,400 self-only / $8,750 family; $1,000 catch-up for age 55+ per IRC § 223(b)(3). IRS Publication 969 (HSAs)
HHS 2026 Federal Poverty Level guidelines: 400% FPL for 1-person household $60,240; 2-person household $81,760. ACA premium tax credit cliff rule restored 2026 after enhanced subsidies expired end of 2025.
One Big Beautiful Bill Act (OBBBA), enacted July 2025: permanently set the IRC § 2010 estate and gift exemption at $15M per person ($30M married with portability election). Eliminates TCJA 2017 sunset previously scheduled for 2026.
CMS Medicare & You 2026: Part B late enrollment penalty = 10% per each full 12-month period without Medicare or creditable coverage. Penalty is permanent and added to the base premium every month. medicare.gov — when does coverage start
CMS 2026 IRMAA brackets: Part B base premium $202.90/month; Tier 1 threshold (MFJ MAGI $218,000–$272,999) adds approximately $73.90/month per person. medicare.gov Part B costs
IRS Rev. Proc. 2025-67 — 2026 long-term capital gains 0% rate threshold: $49,450 taxable income (single) / $98,900 (married filing jointly). IRS Topic 409 — Capital Gains and Losses
SSA Publication No. 05-10069 (2026): Earnings test limits — $24,480/year ($2,040/month) under FRA; $65,160/year ($5,430/month) in year of FRA. Reduction: $1 per $2 of excess under FRA; $1 per $3 in FRA year. SSA — working while receiving benefits
IRC § 86 — Social Security income taxation thresholds: $25,000/$34,000 single; $32,000/$44,000 MFJ combined income (AGI + nontaxable interest + ½ SS). Thresholds set by statute since 1984/1993; not indexed for inflation. SSA — income taxes and Social Security
IRS Notice 2025-67 — 2026 QCD annual limit $111,000 per IRA owner per IRC § 408(d)(8) as amended by SECURE 2.0 § 307 (indexed for inflation from 2024). IRS Publication 590-B (IRA distributions)

Values verified as of May 2026. Tax law changes frequently — confirm current figures at IRS.gov and SSA.gov before making financial decisions.