Year-End Tax Planning Checklist for High-Net-Worth Individuals (2026)

For $5M–$50M households, Q4 is the highest-leverage tax planning period of the year. Roth conversions, tax-loss harvesting, charitable giving, RMDs, and retirement contributions all have hard December 31 or April 15 deadlines. A Roth conversion not completed by midnight on December 31 cannot be done retroactively. This checklist covers the key actions and deadlines for 2026, in priority order for most HNW households.

Bracket headroom calculator

Enter your estimated 2026 gross ordinary income (wages, business income, 1099-R, consulting — before deductions) to see your federal tax bracket and Roth conversion capacity. Your 2026 income also determines your 2028 Medicare IRMAA tier — the 2-year lookback means income decisions you make this year affect Medicare premiums two years from now.

1. Roth conversion window

Deadline: December 31. Roth conversions cannot be backdated or extended. The amount converted adds to ordinary income in the conversion year and must be reported on the tax return for that year.

• Fill-the-bracket strategy. Convert up to the ceiling of your target bracket. A couple with $180K of ordinary income has roughly $223,000 of headroom in the 24% bracket (see calculator above). Converting $223K at 24% pays $53,520 in federal tax now to permanently eliminate RMDs and future taxes on that balance.
• IRMAA 2-year lookback. A large Roth conversion in 2026 affects your 2028 Medicare premiums. The jump from the base tier to Tier 1 (MFJ $218K) costs an extra $1,948/year for a couple. Weigh the lifetime Roth benefit against the 2-year IRMAA surcharge before converting past a tier. See the IRMAA planning guide for tier-by-tier math.
• No recharacterization. Roth conversions have been irrevocable since 2018. There is no "undo" after December 31.
• State tax consideration. If you're planning a domicile change to a no-income-tax state (FL, TX, NV, WA), deferring the conversion to after your residency is established can save 5–13% in state income tax. See the state tax planning guide.

→ Full guide: Roth Conversion Strategy for HNW Investors

2. Required minimum distributions

Deadline: December 31 (first-ever RMD may be delayed to April 1 of the following year — but taking two RMDs in one year stacks ordinary income and can push you into a higher bracket and higher IRMAA tier).

• RMD ages. Age 73 if born 1951–1959; age 75 if born 1960 or later (SECURE 2.0 § 107).⁵
• QCDs satisfy RMDs tax-free. A qualified charitable distribution (QCD) directly from your IRA to a 501(c)(3) satisfies your RMD, excludes the amount from MAGI entirely (not just a deduction), and counts toward the $111,000 annual QCD limit for 2026. For HNW households, QCDs are typically better than taking the RMD, paying tax, and then donating — especially if you're already claiming the standard deduction.³
• QCD custodian deadline. The QCD check must be received by the charity by December 31. Most custodians need 5–7 business days to process; initiate by mid-December.
• QLAC option. A Qualifying Longevity Annuity Contract (QLAC) allows you to carve out up to $210,000 from your IRA for RMD purposes, deferring distributions from that portion to age 85. Useful for reducing early RMD income while covering longevity risk.

→ Full guide: RMD Planning for High-Net-Worth Retirees

3. Tax-loss harvesting

Deadline: typically December 28–30 (trades must settle by December 31; most brokerages require trade execution 2–3 business days before year-end — confirm your custodian's cutoff date).

• Pair losses with gains. Identify unrealized losses in your taxable portfolio. Sell to realize the loss and use it to offset realized gains elsewhere. At the 23.8% federal rate (20% LTCG + 3.8% NIIT), each $100K of offsettable LTCG sheltered saves $23,800.
• Wash sale rule (IRC § 1091). Do not repurchase a "substantially identical" security within 30 days before or after the sale. Use ETF pairs (e.g., sell VTI and buy SCHB) to maintain market exposure. Mutual fund-to-ETF swaps often qualify if the funds have meaningfully different holdings.
• Short-term losses first. Short-term losses offset short-term gains (taxed as ordinary income — rates up to 37%). After offsetting same-type gains, excess losses can offset opposite-type gains. Strategic ordering matters.
• Know when TLH destroys value. Harvesting losses in assets you plan to leave to heirs wastes the step-up in basis at death. Harvesting in a year when you'll convert to a domicile-change state creates gains at the higher pre-move rate. See the TLH strategy guide for when harvesting creates vs. destroys value.

→ Tools: Direct Indexing TLH Calculator · Tax-Loss Harvesting Guide

4. Retirement account contributions

• 401(k) contribution changes via payroll. If you're not on track to max your 401(k), change your deferral percentage now. Most payroll systems need 2–4 weeks to process changes. December contributions via payroll require action by November.
• Super catch-up for ages 60–63. SECURE 2.0 allows $11,250 in additional catch-up (rather than $8,000) for participants who turn 60, 61, 62, or 63 in the calendar year. At a 37% marginal rate, the extra $3,250 saves $1,202 in federal tax alone.¹
• High earner catch-up Roth requirement. If you earned more than $150,000 in 2025, your 401(k) catch-up contributions must be Roth (after-tax) starting in 2026. Confirm your plan allows Roth catch-up before year-end.
• New solo 401(k) plan establishment. December 31 is the last day to establish a new solo 401(k) plan for 2026 contributions. You cannot establish a plan and retroactively apply it. Contributions themselves can be made up to the tax filing date plus extension.

→ Full guide: Cash Balance Plan + Solo 401(k) for HNW Business Owners · Backdoor and Mega Backdoor Roth

5. Charitable giving

Deadline: December 31 for the deduction to count in the 2026 tax year.

• Cash donations. Cash or check postmarked by December 31 qualifies. Credit card charges made by December 31 qualify even if the bill is paid in January. Subject to the 60% AGI deduction limit; 35% cap for 37% bracket taxpayers under OBBBA 2026 rules.
• Appreciated stock to DAF. The most tax-efficient charitable move at HNW: donate long-term appreciated stock directly to a donor-advised fund. You bypass capital gains entirely and get a full fair market value deduction (up to 30% of AGI). Funds in the DAF can then be granted to charities over time. Brokerage transfers typically require 5–7 business days — initiate by mid-December to ensure settlement before year-end.
• QCDs from IRA. If you're 70½ or older, up to $111,000 of IRA distributions made directly to charity in 2026 are excluded from MAGI — not just a deduction, but a MAGI reduction. This keeps income below IRMAA tiers and avoids the OBBBA's 0.5% AGI floor for itemized charitable deductions.³
• Bunching strategy. If your regular annual giving is $15,000–$20,000, consider combining 2–3 years of donations into a single DAF contribution this year. The single-year lump sum may exceed your standard deduction threshold ($32,200 MFJ), generating an itemized deduction while future grants come from the DAF.

→ Full guides: DAF Tax Strategy for HNW Donors · Charitable Remainder Trust (CRUT) · Charitable Lead Annuity Trust (CLAT)

6. Annual gifting and estate moves

• Annual exclusion gifts. Each donor can give $19,000 per recipient in 2026 without using any lifetime exemption and without filing Form 709.⁴ A married couple can give $38,000 to each child, grandchild, or other individual. These exclusions do not carry over — use them or lose them by December 31.
• 529 superfunding. Contribute up to $95,000 per beneficiary (single) or $190,000 (married, gift-splitting) to a 529 in one year by electing 5-year gift proration on Form 709. The full amount leaves your estate immediately. No income tax deduction federally, but the estate reduction is dollar-for-dollar.⁴
• Direct tuition payments (IRC § 2503(e)). Payments made directly to an educational institution for tuition are excluded from the gift tax entirely — no limit, no Form 709 required. This is in addition to the $19,000 annual exclusion.
• Trust distributions. Irrevocable trust income distributed by December 31 is taxed to beneficiaries at their marginal rate rather than compressed trust bracket rates. Alternatively, the 65-day rule (IRC § 663(b)) allows fiduciary distributions made within 65 days of year-end (i.e., by March 6, 2027) to be treated as 2026 distributions if elected. See the trust income tax planning guide for the bracket compression math.
• GRAT shelf life. GRATs must be funded and term must begin in the year the rate lock is set. The § 7520 hurdle rate (5.0% in May 2026) applies to GRATs funded during that period. A GRAT funded in December 2026 locks in the December rate — if rates fall, defer; if you expect asset returns well above the hurdle, fund before year-end.

→ Full guides: Multi-Generational Wealth Planning · GRAT, SLAT, and IDGT Strategies · Trust Income Tax Planning

7. Business owner items

• New retirement plan establishment. December 31 is the last day to establish a new solo 401(k) or cash balance plan for the 2026 tax year. Cash balance plans require actuarial design — engage a TPA by October; don't wait until December. A 58-year-old netting $900K can shelter $320,000+ in a combo solo 401(k) + cash balance plan.
• Section 179 and bonus depreciation. Equipment, machinery, and qualifying property must be placed in service by December 31 to take the deduction in 2026. Under OBBBA, 100% bonus depreciation is permanently restored for qualifying property placed in service after January 19, 2025.⁶ For a practice or business in the 37% bracket, a $200,000 equipment purchase deducted in 2026 saves $74,000 in federal income tax.
• S-corp W-2 finalization. Your 2026 W-2 must be finalized before year-end for S-corp owner retirement plan contribution limits (employer contributions are limited to 25% of W-2 compensation). Review your reasonable compensation calculation before December 31.
• QBI deduction (IRC § 199A). The Qualified Business Income deduction is permanently 23% under OBBBA for pass-through income from sole proprietorships, partnerships, and S-corps (within income limits). Coordinate with your CPA to optimize W-2 wages and qualified property to maximize the deduction before year-end.⁶
• NQDC distribution elections. Non-qualified deferred compensation plan elections for the 2027 plan year must typically be made by December 31, 2026 under Section 409A rules. If you participate in a NQDC plan, review distribution timing elections now.

→ Full guides: Cash Balance Plan Guide · Non-Qualified Deferred Compensation · Business Exit Planning

Deadline calendar

Sources

1. IRS — 401(k) limit increases to $24,500 for 2026; IRA limit increases to $7,500. Employee deferral $24,500; catch-up $8,000 (age 50+); super catch-up $11,250 (ages 60–63); IRA $7,000/$8,000; HSA limits from IRS Notice 2025-19. Values verified June 2026.
2. IRS Notice 2025-67 — 2026 Retirement Plan Amounts. HSA family limit $8,750; individual $4,400; catch-up $1,000 (age 55+). Values verified June 2026.
3. IRS Notice 2025-67 — QCD limit $111,000 for 2026; QLAC limit $210,000. Verified June 2026.
4. IRS — 2026 Tax Inflation Adjustments including OBBBA amendments. Annual gift exclusion $19,000; estate/gift exemption $15M (OBBBA, permanent). Verified June 2026.
5. IRS — Required Minimum Distributions (RMDs). SECURE 2.0 § 107: RMD age 73 (born 1951–1959) or 75 (born 1960+). Verified June 2026.
6. IRS — OBBBA provisions: 100% bonus depreciation permanently restored for qualifying property; QBI deduction permanently 23%. Verified June 2026.

Tax limits verified as of June 2026 against IRS.gov and Rev. Proc. 2025-32 / IRS Notice 2025-67. Dollar amounts are subject to annual inflation adjustment. Consult a tax advisor for your specific situation.

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