Year-End Tax Planning Checklist for Wealthy Families (2026)

Most of the highest-value tax moves for $2M–$20M households expire December 31. Miss the deadline and you've paid 37¢ on dollars you didn't have to. This checklist covers all 47 actions — retirement contributions, Roth conversions, RMDs, tax-loss harvesting, charitable giving, estate gifting, business moves, and this year's one-time QOZ 1.0 deadline — with interactive checkboxes to track your progress.

2026 is unusual: the QOZ 1.0 deadline hits December 31. Investors who deferred capital gains into a Qualified Opportunity Fund anytime between 2018 and 2021 will have all of those deferred gains recognized on December 31, 2026 — regardless of whether they sell. This one-time recognition event adds meaningfully to 2026 MAGI for IRMAA purposes and can push investors into higher brackets. If you invested in a QOF, plan for this tax hit now. See our QOZ planning guide for details.

How to use this checklist

Check each item as you complete it or confirm it's not applicable. Items are grouped by category and sorted by deadline urgency. Hard December 31 deadlines are marked DEC 31. Items with January and April deadlines are noted separately.

Progress: 0 of 47 items checked 0%

1. Retirement contributions — most deadlines: Dec 31 or April 15, 2027

Maximizing tax-deferred contributions is the highest-return, lowest-complexity move for high earners. 2026 limits per IRS Notice 2025-67:¹

Account	2026 limit	50+ catch-up	60–63 super-catch-up	Deadline
401(k) / 403(b) employee deferral	$24,500	+$8,000 = $32,500	+$11,250 = $35,750	Dec 31
Traditional / Roth IRA	$7,500	+$1,000 = $8,500	—	Apr 15, 2027
HSA (family HDHP)	$8,750	+$1,000 = $9,750	—	Apr 15, 2027
Solo 401(k) — employee deferral	$24,500	+$8,000–$11,250	—	Dec 31
Solo 401(k) — employer contribution	Up to §415(c) $72,000 total	—	—	Tax filing + extension

Confirm 401(k)/403(b) deferral elections are on track to hit $24,500 ($32,500 if 50+; $35,750 at ages 60–63). Dec 31 deadline for elections. If ages 60–63: verify your plan allows the SECURE 2.0 super-catch-up ($11,250 vs. $8,000) — not all plans have adopted it yet. Dec 31. Note: SECURE 2.0 requires all catch-up contributions to be Roth if your prior-year wages exceed $150,000 (effective 2026). Confirm your plan's updated payroll withholding reflects this. IRA / backdoor Roth: if income is above the $252,000 MFJ Roth IRA phaseout, plan the two-step backdoor Roth. Execution can wait until April 2027 for the 2026 tax year, but contribution in December gives your custodian time to process. See our backdoor Roth guide. HSA: if enrolled in a qualifying HDHP all year, confirm you're on track for the $8,750 family limit (or $4,400 self-only). Can contribute through April 15, 2027, but investing now gives an extra quarter of tax-free growth.

2. Roth conversions — Dec 31 hard deadline

The Roth conversion window is most valuable in the years between retirement and RMD onset (ages 62–72) — but any year with a lower-than-usual income qualifies. Conversions must be complete by December 31 of the tax year; there's no extension. See our full Roth conversion guide.

Estimate your 2026 MAGI now (before year-end). Identify the headroom between your projected income and the top of your current bracket (35% bracket ceiling: $768,700 MFJ; 32% ceiling: $512,450 MFJ). Model IRMAA: check if a Roth conversion will cross a Medicare surcharge threshold two years from now. The first IRMAA tier kicks in at $212,000 MFJ 2026 MAGI (affecting 2028 premiums). Use our IRMAA calculator. If you have deferred QOZ gains recognizing December 31, 2026 (see alert above): that income spike may make 2026 a poor year for additional Roth conversions — or it may have already consumed your bracket headroom. Adjust accordingly. If you're in the ages 62–72 window with a large traditional IRA: prioritize converting the amount that fills the 22% or 24% bracket before RMDs begin and push you into 32–37%. Execute conversion with your custodian by Dec 31. Confirm Roth 401(k) balance: SECURE 2.0 §325 eliminated lifetime RMDs from Roth 401(k)s starting in 2024. No Dec 31 action required, but verify your plan has updated its administration rules.

3. Required minimum distributions (RMDs) — Dec 31 hard deadline

RMD failure triggers a 25% excise tax (reduced to 10% if corrected within the correction window). SECURE 2.0 raised the starting age: 73 for those born 1951–1959; 75 for those born 1960 or later.² See our full RMD planning guide.

Confirm whether you (or your spouse) are subject to RMDs in 2026. Born 1951–1953: RMD age is 73. Born 1960+: RMD age is 75. Know your Required Beginning Date. Calculate each account's 2026 RMD: prior year-end balance ÷ IRS Uniform Lifetime Table divisor for your age. Verify your custodian's RMD calculation if they auto-process — errors happen. All RMDs must be withdrawn by Dec 31. QCD (Qualified Charitable Distribution): if 70½+ and charitably inclined, direct up to $111,000 in 2026 directly from your IRA to a qualified charity. Satisfies RMD, excluded from MAGI, reduces IRMAA exposure, can't go to a DAF. Must be completed by Dec 31. Inherited IRA (non-EDB): if you inherited a traditional IRA from someone who was past their Required Beginning Date, you owe an annual RMD in years 1–9 of the 10-year window (T.D. 10001). The 25% excise tax applies for missed distributions after 2024. Dec 31. See our inherited IRA guide. Still working exception: if you're still employed at year-end and your plan allows it, you may be able to defer the current employer's 401(k) RMD until April 1 of the year following retirement. Confirm with your plan administrator.

4. Tax-loss harvesting & investment moves — typically Dec 26 or earlier for settlement

Sales need to settle for the loss to count in the tax year. For stocks, this is T+1 settlement; for mutual funds, check your fund's year-end cut-off dates. Practical deadline: execute by December 26 to ensure settlement by December 31. See our tax-loss harvesting guide.

Review taxable account for unrealized losses. For positions down more than 10–15% with a tax basis above current market, consider harvesting the loss now (buy a correlated but not "substantially identical" replacement). At 37% + 3.8% NIIT, $50K in harvested losses is worth $20,400 in deferred tax. Wash sale check: you cannot repurchase the same (or substantially identical) security within 30 days before or after the sale. Swap into a similar-but-different ETF. Flag any recent purchases of the same security in the prior 30 days that would trigger a wash sale already. Net short-term vs. long-term gains: losses offset gains of the same type first, then cross-type. Prioritize harvesting losses to offset any short-term gains you've already realized (taxed at 37% vs. 23.8% for long-term). Direct indexing: if your taxable account is $250K+, confirm your manager has been running systematic harvesting throughout Q4 and has a year-end plan. Many direct-indexing platforms auto-harvest, but verify your customization settings are correct. Capital gain timing: if you're considering selling a large appreciated position, evaluate whether waiting until January pushes the gain into next year's tax calculation. Sometimes a 3-week delay is worth $50,000+ in deferred tax. Coordinate with your estimated tax plan. See our capital gains strategies guide. Rebalance inside tax-advantaged accounts: use this time to restore target allocation inside IRAs and 401(k)s where rebalancing creates no taxable events. Don't do large rebalancing in taxable accounts at year-end without a tax-lot review.

5. Charitable giving — Dec 31 for most; verify DAF timing

Charitable deductions are available in the year contributed, not the year distributed from a DAF. Bunching multiple years of giving into a DAF in a single high-income year often maximizes the deduction. For full strategy details, see our charitable giving guide.

Donate appreciated stock directly (to charity or a Donor Advised Fund): you deduct the full fair market value and pay zero capital gains tax on the embedded gain. On a $100K position with a $10K basis, you save ~$20,000 vs. selling first. Must contribute by Dec 31. Donor Advised Fund: if you want a current-year deduction but haven't decided which charities to support, contribute to a DAF by December 31. You receive the deduction now; grant recommendations can be made at any time in the future. Charitable bunching: if you give $15,000–$20,000/year, consider contributing 3–5 years of planned giving to a DAF in a high-income year. This converts below-threshold giving into a deductible lump-sum above the $32,200 MFJ standard deduction. OBBBA rule: for 2026, the new floor for the charitable deduction is 0.5% of AGI (if you itemize). Verify your charitable deduction plan under current OBBBA rules. The 35% cap on charitable deductions for high earners also applies — confirm with your CPA. QCDs (70½+, see RMD section above): $111,000 annual limit. Cannot go to a DAF — must go directly to a qualified public charity. Satisfies RMD dollar-for-dollar and excludes the amount from MAGI. Confirm your IRA custodian's year-end QCD processing deadline (often Dec 20–26). Dec 31 deadline.

6. Estate & gifting moves — Dec 31 for annual exclusion gifts

The annual exclusion gift resets to zero January 1. Gifts not made by December 31 cannot be carried forward. See our full family gifting guide and estate planning guide.

Annual exclusion gifts: each donor can give $19,000 per recipient in 2026 ($38,000 if married and gift-splitting) without using lifetime exemption. A couple with 3 children and 4 grandchildren can transfer $266,000 gift-tax-free this year. Must be completed by Dec 31. 529 superfunding: contribute up to $95,000/donor ($190,000/donor if married, gift-splitting) per beneficiary via the 5-year election under §529(c)(2)(B). Removes the amount from your estate immediately. OBBBA doubled K-12 annual distributions to $20,000/student. Fund by Dec 31 to start the 5-year election clock in 2026 rather than 2027. Direct tuition payments (§2503(e)): unlimited tuition paid directly to an educational institution is excluded from gift tax — not subject to the $19,000 annual limit and doesn't use lifetime exemption. Must be paid directly to the school. Dec 31 for this year's payments. GRAT rollovers: if you have a 2-year GRAT expiring this year, confirm the final annuity payment is processed on schedule. Consider setting up a new rolling GRAT before year-end to restart the §7520 rate clock (May 2026 §7520 rate: 5.00%). Assets growing above 5.00% transfer to heirs gift-tax-free. See our trust strategies guide. OBBBA $15M exemption is permanent — no sunset. The urgency to "use it or lose it" before a sunset has been eliminated. However, the exemption doesn't grow with inflation under OBBBA; future legislative changes remain possible. Continue using annual exclusions and GRATs as efficient transfer tools.

7. Business owner moves — Dec 31 for most, some to filing + extension

Business owners have more year-end levers than employees. Most of the high-value ones have hard December 31 deadlines. See our cash balance plan guide and income tax strategies guide.

Cash balance plan establishment: if you want to shelter $95,000–$255,000+ in a defined benefit cash balance plan for 2026, the plan must be established by December 31, 2026 (despite SECURE 2.0 §317 permitting retroactive plan adoption for profit-sharing — cash balance requires calendar-year establishment). Engage a TPA immediately if you haven't. Dec 31. Section 179 and bonus depreciation: any equipment, machinery, or qualifying property placed in service by December 31 qualifies for 100% first-year expensing under the OBBBA, which permanently restored 100% bonus depreciation for property placed in service after January 19, 2025. If you need equipment, buy and deploy it before year-end. Dec 31 placed-in-service deadline. S-corp reasonable compensation: finalize your W-2 salary through December payroll. W-2 compensation determines the 25%-of-W-2 employer 401(k) contribution limit and the §199A QBI deduction W-2 wage test. Payroll must clear by December 31. PTET (Pass-Through Entity Tax) election: if you're in a high-state-tax jurisdiction (CA, NY, NJ, IL, etc.) and haven't made the PTET election, check whether your state allows a late election. The SALT workaround lets the entity deduct state tax at the entity level, bypassing the $10,000 individual SALT cap. Installment sale timing: if you're selling a business or real estate this year, evaluate whether structuring as an installment sale under §453 defers gain recognition into lower-income years. Must be established before year-end, before closing. See our business sale planning guide. QBI deduction (§199A): for pass-through income eligible for the 23% deduction (OBBBA made this permanent), confirm you're above or below the MFJ $394,600 phaseout ceiling where W-2 wage limits begin to bind. Business structure decisions made before year-end can affect eligibility.

8. IRMAA & Medicare planning — Dec 31 for 2028 premium impact

Medicare Part B and D premiums are based on your MAGI from two years prior. 2026 income determines 2028 Medicare costs. The five-tier surcharge system adds up to $487/month per person in Part B premiums. See our IRMAA planning guide with the full 2026 bracket table and calculator.

Calculate your projected 2026 MAGI now. Check which 2028 IRMAA bracket you'll land in, including any one-time events (business sale, QOZ recognition, Roth conversion, large capital gains). Use the interactive calculator on our IRMAA planning page. If a one-time income event is pushing you into a higher IRMAA bracket for just one year, file a Life-Changing Event (LCE) appeal (Form SSA-44) in 2028. Document the one-time nature of the income event now while records are fresh. QCDs reduce MAGI dollar-for-dollar (see Section 3 above). If you're borderline between IRMAA tiers, a QCD in December may be the single highest-ROI move — $111,000 out of MAGI can save $5,844+/year per person in Medicare premiums for two years.

9. AMT & ISO exercise planning — Dec 31

Alternative Minimum Tax exposure shifted in 2026 due to OBBBA changes. The OBBBA reset the AMT phaseout rate to 50% and lowered phaseout thresholds — more high earners may owe AMT than under prior law. See our AMT planning guide with a 2026 calculator.

Run a 2026 AMT projection before year-end. 2026 AMT exemption: $140,200 MFJ / $90,100 single; phaseout begins at $1,000,000 MFJ / $500,000 single at 50% rate (OBBBA change). Know whether you're in AMT territory before making additional ISO exercises. ISO exercise timing: incentive stock options create an AMT preference item in the year exercised. If you have ISOs, model the spread between exercise and FMV vs. your available AMT exemption before exercising more in December. Exercises must be before Dec 31 to count for this tax year. AMT credit (Form 8801): if you paid AMT in a prior year from ISO exercises, check whether you can recover some of that as a refundable credit against regular tax this year. This runs automatically but review with your CPA to ensure it's being tracked.

10. Estimated taxes & withholding — Q4 due Jan 15, 2027

Q4 estimated tax is due January 15, 2027. The 110% safe harbor (for AGI above $150,000) is based on prior-year tax. Underpayment penalty is currently calculated at the federal short-term rate + 3%. Year-end is the time to confirm you've covered it.

Verify you'll meet the safe harbor: either pay 100% of your 2025 tax (110% if 2025 AGI exceeded $150,000) OR 90% of your 2026 actual tax liability. If Q1–Q3 payments are insufficient, make up the gap by January 15, 2027. Adjust W-4 if you have W-2 income: increasing year-end withholding is often simpler than making a separate estimated payment. Unlike estimated payments, W-2 withholding is treated as paid evenly throughout the year (not as a December lump sum) for penalty calculation purposes. QOZ recognition: if you have deferred QOZ gains recognizing on December 31, 2026 (see alert at top), this will increase your 2026 tax liability significantly. Ensure your Q4 estimated payment or December withholding covers the additional tax to avoid an underpayment penalty.

Not sure where to start? The highest-ROI moves for most $2M–$20M households in a typical year are: (1) max 401(k) + cash balance plan contributions, (2) Roth conversion to top of current bracket, (3) QCDs if 70½+ and charitably inclined, (4) harvest losses in the taxable account, and (5) annual exclusion gifting. If you're only going to do five things, do those five. If this year is unusual — business sale, large inheritance, QOZ recognition, large equity comp vesting — model the full picture with an advisor before December 31.

Get help executing your year-end plan

Many of these moves require coordinated execution — Roth conversion amounts tied to your Roth conversion model, tax-loss harvesting tied to your IRMAA ceiling, charitable giving tied to your DAF balance, and cash balance plan paperwork. If you want an advisor who has done this for dozens of $2M–$20M households and knows which deadlines are firm vs. flexible, fill out the form below.

Sources

IRS Notice 2025-67 — 2026 retirement plan contribution limits: 401(k) $24,500, catch-up 50+ $8,000, super-catch-up 60–63 $11,250, IRA $7,500. irs.gov/newsroom/401k-limit-increases-to-24500-for-2026
SECURE 2.0 Act of 2022, §107 — RMD age 73 for born 1951–1959; §107 RMD age 75 for born 1960+. congress.gov (SECURE 2.0)
IRS Rev. Proc. 2025-19 — 2026 HSA limits: $4,400 self-only / $8,750 family. irs.gov/pub/irs-drop/rp-25-19.pdf
IRS Rev. Proc. 2025-32 — 2026 tax brackets; standard deduction $32,200 MFJ. irs.gov newsroom 2026 adjustments
OBBBA (One Big Beautiful Bill Act, July 2025) — permanent $15M estate/gift exemption; §199A QBI deduction permanent at 23% with expanded phase-outs; 100% bonus depreciation permanent; AMT phaseout rate raised to 50%, threshold reset to $1M MFJ. congress.gov
IRS Publication 969 (2026) — HSA contribution limits and catch-up rules. irs.gov/pub 969

All 2026 values verified as of May 2026. Values subject to change with additional IRS guidance.

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