June 2026 Tax News Roundup — Key Updates for NYC Businesses & High-Net-Worth Individuals
June 2026 Tax News: A Real Deadline, and OBBBA Stops Being Theoretical
Filing season is behind us, but June didn’t coast. The 15th was a live deadline — second-quarter estimates for anyone earning income without withholding, and the return deadline for Americans living abroad. Meanwhile the One Big Beautiful Bill Act stopped being a headline and started being paperwork: final rules on tipped income, permanence for Opportunity Zones, restored first-year expensing for research costs, and the opening of Trump Account elections all landed inside the month.
Enforcement got sharper too. A federal court upheld a $2.3 million willful FBAR penalty and made clear that “I didn’t know” is a weak defense. And the states kept legislating — California added a 12.5% credit haircut for a short June 15 pass-through prepayment, and Cook County managed to be both late with one set of bills and early with a reassessment appeal window.
Key Takeaway
Two things that don’t wait: if you owe quarterly tax, the June 15 estimate already came due — reconcile it now rather than at year-end. And if your business did any product, software, or process development in 2022 through 2024, the retroactive Section 174A research-expensing refund election closes around July 6. That is a decision to make this week, not next quarter.
The IRS Shipped a Look-Back Interest Calculator for Long-Term Contracts
In IR-2026-70, the IRS released a computational tool for the look-back interest method that applies to long-term contracts reported under the percentage-of-completion method. If you run a construction, engineering, or manufacturing business that files Form 8697, this is the annual math that reconciles estimated versus actual contract profit and charges or credits interest on the difference. The calculator won’t change what you owe, but it removes a genuinely tedious source of preparer error.
The New 1% Remittance Transfer Tax — and Who Actually Escapes It
The 1% remittance transfer tax took effect January 1, 2026, and June brought proposed IRS rules that narrow it considerably. Under the proposal, the tax lands on cash-funded transfers handed across a counter — not on bank-wire, ACH, or debit- and credit-card-funded transfers. For most of our business and higher-income clients moving money electronically, that means the tax is largely avoidable by how the transfer is funded. The comment window on the proposed regulations closed June 12.
Trump Accounts Are Open: Claim the $1,000 for an Eligible Child
The IRS switched on Trump Account elections inside the Individual Online Account in late May, and the first $1,000 federal seed deposits begin July 4. Any child born from 2025 through 2028 is eligible for the seed, with a $5,000 annual contribution cap for 2026 and 2027. One caveat worth stating plainly: the account is funded with after-tax dollars and taxed on the way out, like a traditional IRA — so where a child has earned income, a custodial Roth often does more work. Claim the free $1,000 regardless.
Connecticut’s Pass-Through Entity Tax: Elective, 6.99%, and an 87.5% Credit
Connecticut’s PE Tax is elective, at 6.99%, and June 15 was simply the second of four equal quarterly installments for calendar-year filers. Underpaying one costs interest at 1% per month and nothing else — Connecticut has no rule that forfeits the election or trims the owners’ credit for a short payment. The number that actually decides whether to elect is the credit itself: owners get back 87.5% of what the entity paid, so 12.5% is the permanent price of the federal deduction. If you operate across the New York, Connecticut, and California PTET regimes, the mechanics differ in each — California is the state with a June 15 prepayment gate and a 12.5% credit-reduction penalty, added by SB 132.
The Estate Tax Closing Letter Fee Is Rising to $76 — and You Probably Don’t Need One
The IRS user fee for an estate tax closing letter is going up to $76. Before anyone pays it, the more useful point is that most estates don’t need the letter at all. An account transcript, pulled free from the IRS, shows the same closing information executors are usually after. For the estates of our high-net-worth clients, the letter is worth the fee only in narrow situations — a fiduciary who wants formal confirmation before distributing, for instance.
Cook County’s 2026 Reassessment Is Mailing — the Appeal Window Is Short
Cook County reassesses property on a three-year cycle, and 2026 is a reassessment year for a large swath of the county. Notices are going out now, and the appeal window at the Assessor’s office — followed by the Board of Review — opens and closes fast. For clients holding Chicago-area real estate, a reassessment year is the moment to check the new market value against reality, because the number set now drives the tax bill for the next three years.
A $2.3 Million FBAR Penalty Held Up — and “I Didn’t Mean To” Didn’t Save It
A federal court upheld a $2.3 million willful FBAR penalty, and the reasoning is the part expats and high-net-worth clients should read. Courts increasingly find willfulness through reckless disregard or willful blindness, not just an admitted intent to hide accounts. If you hold foreign financial accounts and have been casual about the annual FinCEN 114 filing, the standard for “non-willful” is narrower than most people assume — and the penalty gap between the two is enormous.
June 15 Was a Real Deadline — Just Not the One the Ads Were Selling
Every June a wave of “Fresh Start” advertising implies the 15th is some special relief deadline. It isn’t. June 15 is the second-quarter estimated tax due date and the automatic filing deadline for U.S. citizens living abroad. Missing the estimate doesn’t trigger an instant notice, but it feeds the underpayment penalty calculation at year-end. The piece separates the actual obligations from the marketing.
The IRS Rebuilt Its Anti-Fraud Playbook Around Your Payroll Provider
The IRS and its Security Summit partners retooled the anti-fraud framework, and the center of gravity moved toward payroll providers and employers. The practical effect for business owners is more verification friction and more responsibility riding on the third party that runs your payroll. If you outsource payroll, this is a good month to confirm your provider’s security posture — because a breach there increasingly becomes your reporting problem.
Cook County Property Tax Bills Are Two Months Late — and That Moves Your Deduction
Second-installment Cook County property tax bills are running roughly two months behind again. Late bills aren’t just an annoyance; for a cash-basis taxpayer, when you actually pay the bill decides which tax year the deduction lands in. A bill that slips from one year into the next can shift a sizable property tax deduction across the calendar — which matters if you’re managing the SALT cap or timing income. Chicago-area owners should plan the payment date deliberately.
No Tax on Tips Is In Effect — and the Service-Charge Trap Will Catch Restaurants
The OBBBA “No Tax on Tips” deduction now has final rules, and there’s a trap buried in the definitions. A voluntary tip qualifies; a mandatory service charge — the automatic 20% on large parties, the built-in banquet gratuity — generally does not. Restaurants that route auto-gratuities to staff as “tips” may be misclassifying wages, and the workers may lose the deduction they expected. Owners in food service should look hard at how their POS system codes each line before year-end.
A New $1,700 Federal Scholarship Tax Credit — New York Didn’t Opt In
OBBBA created a federal tax credit of up to $1,700 for donations to qualifying scholarship-granting organizations. The catch is structural: the credit only reaches donors in states that opt into the program, and New York didn’t. So a New York resident writing the same check a New Jersey or Florida resident writes may get nothing back federally for it. If charitable giving to education is part of your plan, where you’re domiciled now changes the answer.
Opportunity Zones Just Became Permanent
OBBBA made the Opportunity Zone program permanent, replacing the old expiration cliff with rolling designations, and IRS Notice 2026-40 fills in the mechanics. For investors sitting on large capital gains, this changes the calculus — the deferral-and-basis-step benefit is no longer racing a sunset date. The tradeoff is the same as it ever was: a real, illiquid investment held for years, chosen on its own merits first and the tax break second.
The R&D Refund Window Closes July 6 — Small Businesses Have to Decide Now
New Section 174A restores immediate expensing of research costs, undoing the five-year amortization that hurt so many small companies. Better still, small businesses can elect to apply it retroactively and reclaim 2022 through 2024 — but the retroactive refund election closes around July 6, 2026. If your company built software, developed a product, or improved a process in those years and capitalized the costs, this is real money with a hard deadline. There’s very little runway left.
What to Watch in July 2026
The nearest cliff is July 6, when the retroactive Section 174A research-expensing election closes. If there’s any chance your business qualifies, that date governs the whole month. July 4 also starts the first Trump Account seed deposits, so families with eligible children will see the $1,000 begin to move.
After that, the calendar quiets before third-quarter estimates come due September 15 — a good window to run a mid-year projection rather than guessing in December. Expect more OBBBA implementation guidance through the summer as the IRS works through tips, overtime, and the Opportunity Zone rules. More on all of it at Helpful Guides. The quiet months are when the good planning gets done — nobody ever saved tax in a panic on April 14.
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