Dangerous counter-trend; compliance challenges; tax-free periods; and other highlights from our favorite tax bloggers.
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Hit "post" too soon
Tax Foundation : Illinois' new social media tax was in the works for months, but it has the appearance of something lawmakers hit "post" on too soon, says the blogger. Illinois plans to impose a complicated, legally fraught new tax based on a few pages of confused, contradictory and almost laughably incomplete legislative text embedded in the new budget. Among the questions the budget writers failed to answer: what, exactly, is being taxed?Armanino : Today, professional services firms are navigating a broader, more complex compliance landscape than they were just a few years ago. New tax legislation, AI adoption, distributed work models and increasing oversight demands are increasing exposure across tax compliance, workforce compliance, data governance and internal controls. As compliance demands grow, even well-run firms can find it harder to keep pace. Here are five challenges driving that strain.The Sales Tax People : In 2026 chief financial officers must treat sales tax compliance as a major priority. They need to automate sales tax processes and choose the right solution without wasting budget on tools that fail to fit their business. The best sales tax automation software isn't the one with the most features. It is the platform that solves multistate compliance challenges while giving finance teams time back for strategic work. This site provides a practical framework for evaluating sales tax automation platforms.TaxConnex : Promotions are an effective way to attract customers and drive revenue, but they can also create unexpected sales tax challenges. Gift cards, loyalty rewards, coupon and promotional discounts all affect a sales transaction differently, and understanding those differences is critical for maintaining compliance. While many businesses assume that any discount automatically reduces the amount subject to sales tax, state tax authorities often take a more nuanced approach.Avalara : A sales tax holiday is a temporary break from sales tax provided by states to encourage purchases of qualifying goods and provide a bit of a tax break for residents. Tax-free periods are generally popular among consumers but can be a tax compliance burden for affected retailers.
Seismic shift
Current Federal Tax Developments : The landscape of clean energy tax planning underwent a seismic shift following the issuance of IRS Notice 2025-42. This technical analysis examines the recent decision by the United States District Court for the District of Columbia in Oregon Environmental Council v. IRS, which fundamentally altered the regulatory framework governing the "beginning of construction" requirements for Section 45Y and Section 48E tax credits.The Tax Times : When most physicians and high‑income professionals think about IRS risk, they picture underreported W‑2 wages or missed 1099s. Recent news out of an Ohio federal court is a reminder that some of the biggest exposures come from complex offshore structures, especially when they touch compensation and practice income.Gordon Law : The IRS has hit some taxpayers with a failure-to-file penalty, a failure-to-pay penalty, an estimated tax penalty or underpayment interest on any return between Jan. 20, 2020, and July 10, 2023. A federal court has now said in Kwong v. United States that those assessments may have been imposed without legal authority. The deadline to protect taxpayers' right to a refund in most cases is July 10. After that date, the door closes, even if the taxpayer would otherwise have won the argument.
The clock is ticking
CLA : The clock is ticking toward a tax event that can't be postponed any longer for those that still hold an Opportunity Zone investment. On Dec. 31, the deferred gain becomes taxable — even if the investment hasn't been sold. To understand how this plays out, learn how the Opportunity Zone investment rules work in practice and some planning strategies to reduce tax liability.Boyum & Barenscheer : Markets reached new all-time highs in May, even as long-term interest rates climbed and inflation remained above expectations. In this market update, Tyler Rudek, chief investment officer at Boyum Wealth Architects, examines the key economic and market trends influencing investors today. The discussion covers rising Treasury yields, stock market valuations, corporate earnings growth and the Federal Reserve's leadership transition. While headlines continue to focus on inflation and interest rates, long-term market performance remains driven by earnings, economic growth and investor discipline.Withum : The IRS has released interim guidance in Notice 2026-16, outlining a major new tax incentive for the manufacturing sector. The guidance implements a 100% special depreciation allowance under IRC Sec. 168(n) for certain commercial real property classified as qualified production property. This provision — enacted as part of the One Big Beautiful Bill Act — allows businesses to immediately deduct the full cost of qualifying production facilities in the year they are placed in service. For companies planning to expand U.S. manufacturing operations, this represents a significant tax planning opportunity.
Springboard for a firm's success
Rosenberg Associates : In those fleeting moments after key deadlines have passed for firms, many leaders plan or consider the idea of a partner retreat. For some, this can be easy to push off. Too many lingering "things to do," much-needed vacations to be taken (nothing wrong with that!), hours of sleep and family time to be made up. But partners that commit, as a leadership group, to spending meaningful time working on their business together will head more confidently into their future, including the next busy season.CBIZ : New York has introduced a new tax targeting high-value second homes — commonly known as a "pied-à-terre" surcharge. The measure is designed to generate additional revenue from non-primary residences, and it could significantly increase tax exposure for certain luxury property owners in New York City. On May 27, the New York State Assembly passed the state's 2026–2027 budget act, and Gov. Kathy Hochul has signed it into law. Effective beginning July 1, 2026, and currently scheduled to sunset on June 30, 2031, the act's provisions create a distinct tax mechanism layered on top of the city's existing real estate tax.Taxjar : AI tools can scan a jurisdiction for relevant rules and structure a tax argument in minutes, tasks that used to anchor a tax professional to their desk for hours. The efficiency gains are real, and they aren't going away. But operating parallel to this speed is a dangerous counter-trend: AI tools have become so good at mimicking professional expertise that it is becoming harder to spot where the data ends and the hallucination begins. Many AI outputs look convincing but do not hold up under scrutiny.
