A Year-End Tax Checklist for Owner-Led Businesses Entering 2026
Owner-led businesses rarely need more year-end ideas. They need a sharper process for deciding which items actually matter before the calendar closes.
Browse by Year
Everything Fortress published in 2025, newest first — the developments and planning windows that defined the year.
17 pieces in this view
Owner-led businesses rarely need more year-end ideas. They need a sharper process for deciding which items actually matter before the calendar closes.
For years, families with transfer-tax exposure planned against a cliff: the elevated estate and gift exemption was scheduled to be cut roughly in half after 2025, and the watchword was "use it or lose it." The One Big Beautiful Bill Act removed the cliff. The exemption is permanently set at $15 million per individual, and the IRS has now confirmed the 2026 figure. The planning question changes accordingly — from racing a deadline to building deliberately at a higher, stable exemption.
The IRS has set the 2026 retirement plan limits, and they come with a complication that ordinary cost-of-living tables do not capture. Beyond the higher deferral and catch-up amounts, two SECURE 2.0 features converge for high earners in 2026: the enhanced catch-up for those aged 60 to 63, and the new rule requiring high earners to make catch-up contributions on a Roth basis. With final regulations now issued, the high-earner deferral decision must be made before year-end — not in January.
The Inflation Reduction Act built a clean-energy credit runway stretching into the 2030s. The One Big Beautiful Bill Act cut most of it short. Consumer credits for electric vehicles and home energy end within months; residential solar ends with the year; and the large tech-neutral credits for wind and solar now hinge on a begin-construction deadline twelve months out. For anyone with a clean-energy decision pending — a purchase, an installation, or a project — the operative fact is now a date.
Qualified small business stock has long offered one of the most powerful exclusions in the Code — but only on an all-or-nothing basis after a five-year hold. The One Big Beautiful Bill Act redesigned it. Stock acquired after July 4, 2025 now earns partial exclusion at three and four years, a higher per-issuer cap, and a higher company-size ceiling. The catch is the date: older stock keeps the old rules. There are now two parallel regimes, and which one applies turns entirely on when the stock was acquired.
The One Big Beautiful Bill Act did two things to capital-investment planning. It made 100 percent bonus depreciation permanent, ending a phase-down that had cut the deduction to 40 percent for 2025. And it created an entirely new provision — a 100 percent deduction for the cost of building U.S. manufacturing facilities, the kind of real property that normally depreciates over 39 years. Both rewrite the timing of capital decisions, and both turn on specific dates that determine whether a given asset qualifies.
For tax years 2022 through 2024, leveraged businesses watched their interest deductions shrink — not because they borrowed more, but because the formula behind the limitation changed in a way that punished capital-intensive companies. The One Big Beautiful Bill Act permanently restored the more favorable formula, effective for 2025. It is a meaningful expansion of deductible interest. But the same law also planted a new trap, set to spring in 2026, for businesses that capitalize interest to work around the limit.
For four filing seasons, businesses that spent money on research had to capitalize and amortize it rather than deduct it — a rule that raised taxable income for companies that had spent nothing new. The One Big Beautiful Bill Act ended that for domestic research, restoring immediate expensing under a new Code section. And for smaller businesses, the relief reaches backward: an election can recover the deductions lost in 2022, 2023, and 2024. The IRS has now told everyone how to claim it.
The One Big Beautiful Bill Act raised the state and local tax deduction cap from $10,000 to $40,000 — a fourfold increase that reads, at first, like the end of the SALT-workaround era. It is not. The new cap is temporary, it phases down sharply above $500,000 of income, and it reverts to $10,000 in 2030. Meanwhile, the pass-through entity tax workaround survived the bill fully intact, including for service businesses. For higher-income pass-through owners, the entity-level election is still the durable strategy.
For years, the planning conversation ran on a countdown: the Tax Cuts and Jobs Act individual rates and the Section 199A deduction were scheduled to expire after 2025, and the question was how to act before the cliff. On July 4, 2025, the One Big Beautiful Bill Act removed the cliff. The rates are permanent, the 20 percent qualified business income deduction is permanent, and the phase-in rules around Section 199A actually improve in 2026. The defensible move now is to retire the deadline-driven plan and build for a stable code.
For families with transfer-tax exposure, 2025 may represent the last full planning window under the temporarily elevated federal estate and gift exemption. That makes delay more costly than usual.
After the January 2025 Los Angeles County wildfires, the IRS postponed nearly every federal deadline falling between early January and mid-October to a single date: October 15, 2025. California's Franchise Tax Board followed. For affected taxpayers, the relief is automatic — but it is not a reprieve so much as a compression. Obligations that normally spread across the year now converge on one day, and a casualty-loss timing election is in play. Both deserve planning, not passive reliance.
On April 10, 2025, the President signed H.J. Res. 25, nullifying the IRS rule that would have treated decentralized-finance front ends as brokers. The repeal was real and consequential — but it was also narrow. The separate, earlier rule requiring custodial brokers to issue Form 1099-DA for 2025 digital-asset sales was untouched. The reporting era did not end. It got smaller, and clearer.
For many owners, the most important 2025 tax question is not what the current deduction is. It is what the business and owner cash-tax picture looks like if Section 199A disappears on schedule.
On January 23, 2025, the Supreme Court stayed one of the injunctions blocking the Corporate Transparency Act. The headlines read as if reporting was back on. It is not. A separate nationwide order still suspends the filing requirement, and FinCEN itself has said companies are not currently required to file. The defensible posture for closely held businesses is narrow and specific: prepare now, file nothing yet, and watch the second case.
Businesses with even modest geographic growth should treat state filing footprint review as a recurring planning task. Exposure often expands quietly through payroll, sales activity, contractors, or inventory placement.
The conversation has now shifted from abstract sunset theory to practical planning. With major Tax Cuts and Jobs Act individual provisions set to expire at the end of 2025, businesses and families should begin identifying which parts of their planning framework are exposed.
Start Here
Several positions opened in earlier years remain live. If one maps to a decision you are weighing, the conversation worth having is a focused one.