Wendland Services Weekly — issue two: the fourth-quarter playbook

Welcome back to the weekly briefing. Several deadlines land in the next three weeks, and the first full tax year under the One Big Beautiful Bill Act closes in December, so this issue covers what to finish before the calendar turns. You can sign up at wendlandservices.com/insights to get each issue by email.

Last issue covered the permanent fifteen million dollar federal estate, gift, and generation-skipping transfer exclusion. This week moves from the estate plan to the year-end plan.

1. Extended returns: September 30 for trusts, October 15 for individuals

Calendar-year trusts and estates on a Form 7004 extension have five and a half months, so the extended 2025 Form 1041 is due Wednesday, September 30, 2026. Individuals who filed Form 4868 must file the 2025 Form 1040 by Thursday, October 15, 2026, and that extension also covered the 2025 Form 709 gift tax return. New York's six-month extension for Form IT-201 and Form IT-203 ends the same day. An extension to file was never an extension to pay, so interest keeps running on any unpaid balance.

2. Charitable giving has a new floor and a new ceiling in 2026

Starting in 2026, itemized charitable deductions count only above one half of one percent of the donor's contribution base, which is generally adjusted gross income. At ten million dollars of adjusted gross income, the first fifty thousand dollars of gifts produces no deduction. Taxpayers in the thirty-seven percent bracket also have itemized deductions reduced by two thirty-sevenths, which limits the benefit to about thirty-five cents per dollar donated. Bunching several years of gifts into one year through a donor-advised fund, and giving stock held more than one year, which is generally deductible at fair market value, are the usual responses. Donors age seventy and a half or older can also send up to one hundred eleven thousand dollars in 2026 from an individual retirement account directly to a charity (not a donor-advised fund) as a qualified charitable distribution, which is excluded from income and can count toward the required minimum distribution.

3. State and local taxes: a bigger cap that many readers will not see

For 2026, the state and local tax deduction cap is forty thousand four hundred dollars, reduced by thirty percent of modified adjusted gross income above five hundred five thousand dollars, but never below ten thousand dollars. Above roughly six hundred six thousand dollars of modified adjusted gross income, the limit is back to ten thousand dollars, and the cap returns to ten thousand dollars for everyone in 2030. The final law kept the pass-through entity tax workaround, so for owners of partnerships and New York S corporations, the entity-level election remains the main route to a federal deduction for state income tax. Electing entities should confirm the December 15 estimated payment and note that the 2027 election window runs from January 1 to March 15, 2027.

4. Opportunity zone gains come due on December 31

Gain deferred into a qualified opportunity fund under the original program is included in income for the tax year containing the earlier of a sale or December 31, 2026, so many investors will owe tax on 2026 returns without any sale proceeds. In Notice 2026-40, the Internal Revenue Service confirmed that this inclusion cannot be rolled into a new fund, though continuing holders can still qualify for the ten-year benefit on later appreciation. On September 10, 2026, the Treasury Department and the Internal Revenue Service also proposed regulations on fund reporting and decertification. Families with fund interests should estimate the 2026 tax now and build it into estimated payments.

5. A fourth-quarter operations checklist

• Harvest losses carefully. A loss is disallowed if substantially identical securities are bought within thirty days before or after the sale.
• Decide on Roth conversions by December 31. Conversions made after 2017 cannot be undone by recharacterization.
• Take required minimum distributions by December 31. Only a first-year distribution can wait until April 1, and a shortfall can face a twenty-five percent excise tax, or ten percent if corrected within two years.
• Fund the fourth-quarter 2026 estimated payment, due January 15, 2027.
• Close the books on every entity. Reconcile bank and brokerage accounts, confirm capital accounts, and gather what your preparers will need for Schedule K-1 season.

Calendar watch

• Wednesday, September 30, 2026: Extended Form 1041 due for calendar-year trusts and estates.
• Thursday, October 15, 2026: Extended Form 1040, Form 709, and New York Forms IT-201 and IT-203 due.
• Tuesday, December 15, 2026: Final New York pass-through entity tax estimated payment for 2026.
• Thursday, December 31, 2026: Deadline for required minimum distributions, Roth conversions, qualified charitable distributions, and loss harvesting; deferred opportunity zone gain is recognized.
• Friday, January 15, 2027: Fourth-quarter 2026 federal estimated tax payment due.
• Monday, March 15, 2027: Deadline for the 2027 New York pass-through entity tax election.

If any of this touches your household, your trusts, or your family office, a second look before year end can be worthwhile. You are welcome to write to marcel@wendlandservices.com.

Wendland Services is an independent practice in Bellmore, New York, focused on accounting, bookkeeping, tax, and consulting for high-net-worth households and family offices.

This note is educational, not advice for your facts, and not an offer of legal services.

— Wendland Services marcel@wendlandservices.com