From TCJA to OBBB: The Last 30 Days of Tax Changes You Can’t Afford to Ignore

Over the last 30 days the tax world hasn’t just “nudged” forward—it’s hit the gas. We’ve got a live 2026 filing season, fresh IRS guidance under the One, Big, Beautiful Bill (OBBB), and some very real planning opportunities (and landmines) you and I need to talk about. 💰

Big Picture: What Changed This Month

Here’s the deal: in the last 30 days, three themes matter for serious taxpayers and business owners:

• The 2026 filing season is officially launching with OBBB provisions now biting for the first time on 2025 returns.
• Treasury/IRS dropped new guidance on permanent 100% bonus depreciation (yes, permanent) and how to actually use it.
• Operationally, IRS capacity and budget noise means enforcement and service will be… let’s say “uneven,” so documentation and planning matter more than ever.

Bottom line: your 2025 return (filed this year) is the first real testing ground for Trump 2.0’s OBBB regime, and the clock just started.

1. Filing Season 2026: Game On

The IRS has now set the official opening of the 2026 filing season and is explicitly warning taxpayers: new OBBB rules are in play for 2025 returns. Think of this as Season 1 of the “OBBB Cinematic Universe.”

Key points you should care about:

• The IRS announced late‑January as the opening of the 2026 filing season and is pushing taxpayers toward online tools and e‑file to cope with service constraints.
• New 2025 law changes—including expanded brackets, updated credits, and new information-reporting forms—are live for returns filed this season.
• IRS is signaling: “Be ready before you hit ‘file’.” Translation for us: planning now, not when the organizer shows up, is where the money is made.

Example: if your 2025 income bounced around (big bonus, liquidity event, extra K‑1s), the interaction of new brackets + OBBB deductions might mean your old “safe harbor” estimates are suddenly wrong.

1. OBBB’s New Star: Permanent 100% Bonus Depreciation

Treasury and IRS just issued formal guidance confirming how the permanent 100% additional first‑year depreciation works under OBBB for property acquired after January 19, 2025. This is the spiritual sequel to TCJA bonus depreciation—only now it’s not scheduled to sunset.

Highlights from the new notice:

• OBBB provides a permanent 100% additional first‑year depreciation deduction for qualified property acquired (or specified plants planted/grafted) after January 19, 2025.
• The notice clarifies when property is eligible, how to determine the bonus amount, and confirms that taxpayers can generally rely on existing bonus depreciation regulations as interim rules.
• Certain qualified sound recording productions are explicitly eligible for the 100% first‑year write‑off, which is wild if you’re in the entertainment/content space.

Planning angle:

Let’s say your operating company buys $5M of qualified equipment in late 2025 and places it in service before year‑end. Under the new OBBB rules and this fresh guidance, you can generally expense 100% in year 1 rather than recovering it over 5, 7, or longer‑year MACRS lives.

For mid‑market owners, this means:

• You can deliberately time capital expenditures around income spikes (big gain, special dividend, sale of a division) to flatten taxable income.
• Entity structure (C‑corp vs S‑corp/partnership), basis, and at‑risk rules matter even more when you light up a massive first‑year deduction.

Friends, this is exactly the kind of rule that looks “simple” and then eats you alive if you ignore placed‑in‑service dates, related‑party rules, or mixed‑use assets.

1. Individual Landscape: Brackets & Deductions Under OBBB

While most of the “big” structural changes were enacted in 2025, we’re now seeing them integrated into IRS guidance and 2026 inflation adjustments—so they are no longer theoretical.

Here’s what’s now baked in for planning:

• The OBBB keeps the seven‑bracket structure and the 37% top rate, with updated income thresholds for 2026; the top 37% rate kicks in over about $640K for singles and $768K for joint filers in 2026.
• The standard deduction is materially higher: for 2026, it increases to about $32,200 for joint filers, $16,100 for singles, and $24,150 for heads of household.
• The old “Pease” itemized deduction phaseout remains gone, but OBBB adds a limitation on the tax benefit of itemized deductions for those in the 37% bracket.

Translation: OBBB gave with one hand and quietly took back with a clever little cap for top‑bracket taxpayers. Very on‑brand.

What this means for strategy:

• If you’re hovering near the 37% bracket, timing of charitable giving, state taxes, and other itemized deductions can determine whether you actually get full value.
• The higher standard deduction continues to push many taxpayers out of itemizing, which affects everything from mortgage decisions to charitable structure (direct gifts vs donor‑advised funds).

Think of the standard deduction as the “cover charge” at the club; you don’t itemize unless your deductions beat that number. For 2026, that cover charge is higher again.

1. Business Owners: QBI, “Permanent” Rules, and Stability (Sort Of)

Let’s be honest: one of the biggest sources of stress the last few years has been, “Is this deduction going away?” OBBB tries to calm that down for businesses.

From current guidance and analysis:

• OBBB makes the 20% Qualified Business Income (QBI) deduction permanent for post‑2025 years, rather than letting it sunset with TCJA.
• It also increases the income thresholds where QBI limitations phase in—from roughly $50K to $75K for individuals and $100K to $150K for joint filers—starting after 2025.
• Bonus depreciation restored and made permanent at 100% under OBBB, reinforcing a “front‑load your deductions” environment for capital‑intensive businesses.

For pass‑through owners, this is huge:

• Entity selection decisions can now be modeled over a longer horizon instead of guessing at sunset dates every election cycle.
• Layering QBI, permanent bonus depreciation, and estate/gifting strategies (with still‑elevated exemptions) means multi‑year planning is back in style.

If TCJA felt like dating someone “temporary,” OBBB is Rome: imperfect, political, but meant to last a long time.

1. IRS Capacity: “Buckle Your Seatbelts”

On the operations side, recent reporting highlights that IRS budget and staffing pressures could impact the 2026 filing season—service levels, processing times, and maybe even how they triage enforcement.

What that implies for you:

• Expect potentially slower responses on notices and more reliance on online self‑service portals. [4] [1]
• The IRS will likely lean on data analytics, information returns, and mismatches (think new forms, crypto reporting, car‑loan interest reporting, and similar) to drive enforcement rather than broad audits.

In other words, they may be “smaller,” but the computers are not. Document your positions. When we push the envelope—as we often should—we want a clean, defensible file.

Action Items: What You Need To Do Now

Friends, here’s where the rubber meets the road:

• Front‑load 2025–2026 CapEx Planning
  If you’re considering major equipment, tech, or facility investments, model a 100% bonus depreciation strategy against your expected 2025–2026 income and cash‑flow needs.
• Re‑Underwrite Your Entity Structure
  With QBI and elevated exemptions made more stable, revisit whether your current mix of S‑corp, partnerships, and C‑corp structures is actually optimal under OBBB—not under old TCJA assumptions.
• Bracket & Deduction Management for HNW
  If you’re near the 37% bracket, timing charitable giving, state tax payments, and large income events can materially shift your net tax because of the new itemized deduction limitation at the top rate.
• Get Filing‑Season Ready Early
  With new rules live and IRS capacity under strain, waiting until March/April to “figure it out” is like going to Easter Mass five minutes before it starts and expecting a front pew.
• Document, Document, Document
  For any aggressive or finely tuned strategy—bonus depreciation, QBI allocations, special classes of property, complex K‑1s—build the file as if an agent will look at it three years from now after a double espresso. Because they might.

The last 30 days have been less “minor tweaks” and more “Act I of a new tax regime.” If your current planning still assumes pre‑OBBB rules, you’re playing last season’s playbook in a new league.

If you want to actually turn these rules into dollars in your pocket rather than footnotes in your return—reach out to us at [email protected] so we can map this to your real-world facts.

Grazie Mille, Ciao.