In the blogs: Are you ready for some football betting?

Synthetic voices; CRAT; cross-border commerce; and other highlights from our favorite tax bloggers.

Are you ready for some football betting?

• Don't Mess With Taxes: As the NFL's 2026 preseason games begin, betting on the United States' favorite sport ramps up, too. Those who wager around $30 billion each season on America's professional football matchups — and $136 billion more on additional sports (and other) events — should remember that their winnings are taxable income.
• CLA: Following the U.S. Supreme Court's decision invalidating the IEEPA tariffs, the government has stopped collecting those tariffs and is refunding amounts importers previously paid. Because tariffs are generally capitalized into inventory and recovered through cost of goods sold as inventory is sold, refunds will be taxed the same as the original tariff. This blog discusses how tariff refunds will be taxed and how companies should manage them.
• Withum: Several notable trade and tariff developments have emerged in recent weeks, affecting businesses engaged in cross-border commerce throughout North America and beyond. Key changes involve the United States-Mexico-Canada Agreement, International Emergency Economic Powers Act tariff refunds and new tariff actions that could have operational and financial implications for importers and exporters.
• Eide Bailly: When companies decide where to locate a new facility, expand operations or build a data center, tax credits and incentives are often a significant factor. For businesses unfamiliar with how these programs work, this blog's "SALT Credits & Incentives: The Playbook – Part I," provides an overview of the incentives landscape and why states offer these benefits. 
• Tax Vox: Senator Ron Wyden, D-Oregon, proposed limiting tax benefits for new data centers and levying a new excise tax "to help the communities and workers most impacted as data center construction continues." He is one of many lawmakers who want to use taxes to address worries that AI could eliminate jobs, inflict environmental harms and have broader negative consequences for society and global security. 

Like pulling teeth

• Hall CPA: Many dentists spend years building successful practices, only to discover that higher income often leads to higher taxes. While maximizing retirement contributions and claiming standard business deductions can help, those strategies only go so far. For dentists who want to build wealth outside their practice, real estate offers more than appreciation and rental income. This blog explains how dentists can use these strategies to legally reduce taxable income while creating another source of long-term financial security.
• Current Federal Tax Developments: For tax professionals, the landmark Supreme Court decision in Boechler PC v. Commissioner was heralded as a major victory for taxpayer rights. In that ruling, the high court settled a long-standing circuit split by holding that the 30-day filing deadline under Internal Revenue Code Sec. 6330(d)(1) to petition the U.S. Tax Court for review of a collection due process determination is a nonjurisdictional limitations period subject to equitable tolling. However, a critical distinction exists between a deadline being subject to equitable tolling and a taxpayer actually qualifying for such relief. 
• Yeo and Yeo: The IRS just released some good news for families considering funding a Trump account. In Revenue Procedure 2026-25, the IRS has provided a safe harbor that allows certain donors to avoid filing a federal gift tax return solely because they made contributions to a Trump account, as long as the safe harbor requirements are satisfied. The guidance is narrow, but it resolves a real problem.
• CBIZ: The IRS issued final regulations on July 9 identifying certain charitable remainder annuity trust arrangements as "listed transactions." The rules focus on transactions involving a single CRAT and a single premium immediate annuity where taxpayers attempt to report CRAT distributions under annuity tax rules rather than under the special ordering rules that apply to CRATs. For taxpayers and advisors, these regulations signal increased IRS scrutiny of such transactions. 
• The Tax Times: The long-running dispute in 3M Co. et al. v. Commissioner centered on whether the IRS could reallocate royalty income from 3M's Brazilian subsidiary to its U.S. parent even though Brazilian law restricted the subsidiary from paying the full arm's-length amount. The case involved 3M's 2006 tax year and a Section 482 adjustment of nearly $23.7 million in additional royalty income.

Can AI help with tax?

• Vertex: Artificial intelligence is changing how businesses work. Marketing teams use AI to draft content. Customer service teams use it to answer questions. Finance teams use it to analyze data. So naturally, tax teams are asking: Can AI help with tax, too? 
• Abrigo: One of the clearest takeaways from Abrigo's 2026 State of Fraud Survey is that consumers are deeply concerned about AI-powered fraud techniques, including fake emails and invoices and synthetic voices used to impersonate executives. In the survey, 65.1% of respondents said they were extremely or very concerned about those techniques, and another 22.1% were moderately concerned.  
• Tax Pro Center: There comes a time in every business' lifecycle when growing pains start to get in the way of progress. There's usually not a specific day when it occurs, and there's no memo from the IRS or the Small Business Administration. It's usually a gradual accumulation of small problems that eventually become impossible to ignore. 

Reasonable assumption

• Taxbuzz: Most people assume that if taxes were withheld from a paycheck, bonus or stock vesting, then the tax has already been handled. It's a reasonable assumption, but it isn't always correct. One of the most common misconceptions in tax is treating payroll withholding and final tax liability as though they answer the same question. They don't.
• Berkowitz Pollack Brant: On June 18, the IRS issued guidance on the pending tax deferral deadline for the original Qualified Opportunity Zone program under the Tax Cuts and Jobs Act and the program changes introduced in 2025 by the One Big Beautiful Bill Act, which is commonly referred to as QOZ 2.0. Taxpayers, including existing and future QOZ investors, qualified opportunity funds holding qualifying property and QOZ businesses, should take the time now to review the proposed regulatory changes and prepare for the risks and opportunities that lie ahead during this transition.
• National Association of Tax Professionals: Fuel costs are common on business returns, but deducting those costs is not the same as claiming the federal fuel tax credit. A taxpayer may have a valid business expense with no credit at all. Eligibility depends primarily on how the fuel was used. Preparers must separate ordinary deductible fuel costs from qualifying gallons that may support a credit or refund.
• Sikich: In financial due diligence, quality of earnings receives most of the attention. It is the headline deliverable and often the figure around which buyers and sellers negotiate. But in a change-of-ownership transaction, the QoE is rarely the only driver of value. Net working capital, debt and debt-like items often more heavily impact what the seller ultimately earns at closing.