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The brave new world of taxing digital bundles

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As the range of digital goods and services expands every day, the tax issues associated with them have only grown, and one of the most complicated issues that retailers, providers, and tax authorities are facing currently involves digital bundling.

Since the beginnings of sales taxation, retailers have been tasked with collecting the total tax from customers and remitting it to the proper tax authorities, according to Scott Peterson, vice president of U.S. tax policy and government relations for Avalara — a fairly straightforward proposition.

“Over time, retailers began putting different products together to sell as a bundled item,” Peterson said. “For example, at Christmas, grocers put together gift baskets with fruit, cheese, a knife, cutting board, etc. When that was done in a state that exempts groceries (and most states do so) fruit and cheese are exempt, but other items are subject to sales tax. States and retailers have struggled to come to consensus on what should be charged for bundled items.”

“Predominant use” is the phrase typically used in taxation. The state wants to determine the motivation driving purchases to arrive at a relatively uniform direction to determine taxation. 

And then came digital products, and with those products, a greater number of things to be bundled together that are treated quite differently from state to state. This started with the telephone industry, and the companies looked to states and Congress to find a rational way to tax, given that some items on the phone bill were exempt from sales tax. And states were all over the board in terms of how they taxed or exempted what was on the telephone bill. 

For example, phone companies used to have warranties to cover phone lines in a user’s house in addition to outside the house. After years of this, telephone companies convinced states to support congressional legislation to allow them to use books and records to prove they remitted the right amount of tax to states, regardless of what was listed on a telephone bill. The telephone companies provide a bill to consumers that shows the portion subject to sales tax — but it’s confusing to consumers, since the companies don’t have to itemize the tax on their bill. 

The current landscape

Today, states have rules in place specific to digital goods and services, according to Peterson. 

“The Multistate Tax Commission has been studying digital goods to figure out if a definition actually represents what’s being sold,” he said. “The MTC has written a research paper on the digital goods industry, and now they are trying to figure out digital goods bundling — whether it’s a bundle of all digital goods, or digital goods bundled with hardware. “

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“It’s very complicated because businesses are so creative, constantly trying to find ways of selling goods produced,” Peterson explained. “The marketing department often doesn’t care what the tax department thinks when a product is in development. This is easy if you’re selling shoes, but in selling digital goods, it becomes very complex.”

“Marketing is driving complexity on the tax side, as there are so many things that can be sold together,” he noted. “Many states exempt real-time digital classes, such as webinars for CPE, for example. But if you record that class and make it available on demand, it’s no longer live. States then treat it as taxable — it’s no longer education, it’s something else, and states are working to determine how to characterize that ‘something else.'”

The MTC’s primary concern is that this situation will only get worse as everything goes digital. 

“The SST [StreamlinedSalesTax] attempted to put together a bundled transaction rule 20 years ago, but it’s now out of date,” said Peterson, who was previously executive director of the SST Governing Board. “MTC is in the discovery phase now of looking at digital goods bundling and taxation. States should be thinking about the complexity that goes with how to charge tax on a portion of a sales price for a bundle with taxable and exempt items. How does a seller prove to an auditor that they charged tax on the one taxable item in a bundle?  The safest practice in selling a bundled package is to itemize each item and only charge sales tax on taxable items.”

“Businesses need to be able to break the bundle apart,” said Peterson. “The fruit and cheese board was an easy exercise in tax and invoicing, but bundled digital goods is a brave new world for businesses and tax authorities. CPAs would recommend having an invoice that is crystal-clear — ‘I’m selling you A,B,C and D. A and D are exempt, so no tax was charged.’ Every day, some retailer creates a new product/service bundle, and it has the potential to reset the taxation conversation. There are no simple answer in this area.”

And things are only getting more complicated: Peterson further referenced a private letter ruling in which the South Carolina Department of Revenue stated that a company’s sales and rentals of digital textbooks purchased for and used in institutions of higher learning as part of a prescribed course of study are exempt, regardless of the format. (Private Letter Ruling #24-3, South Carolina Department of Revenue, March 18, 2024.)

This is only the latest in a series of state developments, including a California case, Bekkerman, that ruled last month on how the state should tax bundled versus unbundled cellphones.

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Tax Fraud Blotter: Crooks R Us

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The shadow knows; body of evidence; make a Note of it; and other highlights of recent tax cases.

Newark, New Jersey: Thomas Nicholas Salzano, a.k.a. Nicholas Salzano, of Secaucus, New Jersey, the shadow CEO of National Realty Investment Advisors, has been sentenced to 12 years in prison for orchestrating a $658 million Ponzi scheme and conspiring to evade millions in taxes.

Salzano previously pleaded guilty to securities fraud, conspiracy to commit wire fraud and conspiracy to defraud the U.S., admitting that he made numerous misrepresentations to investors while he secretly ran National Realty. From February 2018 through January 2022, Salzano and others defrauded investors and potential investors of NRIA Partners Portfolio Fund I, a real estate fund operated by National Realty, of $650 million.

Salzano and his conspirators executed their scheme through an aggressive multiyear, nationwide marketing campaign that involved thousands of emails to investors, advertisements, and meetings and presentations to investors. Salzano led and directed the marketing campaign that was intended to mislead investors into believing that NRIA generated significant profits. It in fact generated little to no profits and operated as a Ponzi scheme.

Salzano stole millions of dollars of investor money to support his lavish lifestyle, including expensive dinners, extravagant birthday parties, and payments to family and associates who did not work at NRIA. He also orchestrated a separate, related conspiracy to avoid paying taxes on his stolen funds.

He was also sentenced to three years of supervised release and agreed to a forfeiture money judgment of $8.52 million, full restitution of $507.4 million to the victims of his offenses and $6.46 million to the IRS.

Marina del Rey, California: Tax preparer Lidiya Gessese has been sentenced to 41 months in prison for preparing and filing false returns for her clients and for not reporting her income.

Gessese owned and operated Tax We R/Tax R Us and Insurance Services from 2013 through 2019 and charged clients $300 to $800. Gessese would then prepare returns that included claims to deductions and credits she knew her clients were not entitled to, including falsely claiming dependents, earned income credits, the American Opportunity Credit, Child Tax Credits, business deductions, education expenses or unreimbursed employee business expenses. The illegitimate claims led to some $1,135,554.64 issued by the IRS for 2010 through 2018.

She failed to report, or underreported, her own income for 2010 through 2018, some of which included improperly diverted funds from clients’ inflated or fraudulent refunds, causing a tax loss of $488,276.

Gessese, who pleaded guilty in April, was also ordered to pay $1,096,034.01 to the IRS and $53,526.95 to her other victims.

Fullerton, California: In Chun Jung of Anaheim, California, owner of an auto repair business, has pleaded guilty to filing false returns for 2015 to 2022, underreporting his income by at least $1,184,914.

He owned and operated JY JBMT INC., d.b.a. JY Auto Body, which was registered as a subchapter S corp. Jung was the 100% shareholder.

Jung accepted check payments from customers that he and his co-schemers then cashed at multiple area check cashing services; the cashed checks totaled some $1,157,462. Jung withheld the business receipts and income from his tax preparer and omitted them on his returns.

He will pay $300,145 in taxes due to the IRS and faces a $250,000 penalty and up to three years in prison. Sentencing is Jan. 31.

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Tucson, Arizona: Tax preparer Nour Abubakr Nour, 34, has been sentenced to 30 months in prison.

Nour, who pleaded guilty a year ago, operated the tax prep business Skyman Tax and for tax years 2016 through 2018 prepared and filed at least 27 false individual federal income tax returns for clients.

These returns included falsely claimed business income that inflated refunds so that he could pay himself large prep fees. Nour’s clients had no knowledge that he was filing false tax returns under their names.

Nour was also ordered to pay $150,154 in restitution to the United States for the false tax refunds.

Farmington, Connecticut: Tax preparer Mark Legowski, 60, has been sentenced to eight months in prison, to be followed by a year of supervised release, for filing false returns.

From January 2015 through December 2017, Legowski was a self-employed accountant and tax preparer doing business as Legowski & Co. Inc. He prepared income tax returns for some 400 to 500 individual clients and some 50 to 60 businesses.

To reduce his personal income tax liability for 2015 through 2017, Legowski underreported his practice’s gross receipts by excluding some client payment checks. He then filed false personal income tax returns that failed to report more than $1.4 million in business income, which resulted in a loss to the IRS of $499,289.

Legowski, who pleaded guilty earlier this year, has paid the IRS that amount in back taxes but must still pay penalties and interest. He has also been ordered to pay a $10,000 fine.

Wheeling, West Virginia: Dr. Nitesh Ratnakar, 48, has been convicted of failing to pay nearly $2.5 million in payroll taxes.

Ratnakar, who was found guilty of 41 counts of tax fraud, owned and operated a gastroenterology practice and a medical equipment manufacturer in Elkins, West Virginia. He withheld payroll taxes from employees’ paychecks and failed to make $2,419,560 in required payments to the IRS. Ratnakar also filed false tax returns in 2020, 2021 and 2022.

He faces up to five years in prison for each of the first 38 tax fraud counts and up to three years for the remaining counts.

Orlando, Florida: Two men have been sentenced for their involvement in the “Note Program,” a tax fraud.

Jasen Harvey, of Tampa, Florida, was sentenced to four years in prison and Christopher Johnson, of Orlando, was sentenced to 37 months for conspiring to defraud the U.S.

From 2015 to 2018, they promoted a scheme in which Harvey and others prepared returns for clients that claimed that large, nonexistent income tax withholdings had been paid to the IRS and sought large refunds based on those purported withholdings. The conspirators charged fees and required the clients to pay a share of the fraudulently obtained refunds to them.

Overall, the defendants claimed more than $3 million in fraudulent refunds on clients’ returns, of which the IRS paid about $1.5 million.

Both were also ordered to serve three years of supervised release. Johnson was also ordered to pay $864,117.42 in restitution to the United States; Harvey was ordered to pay $785,858.42 in restitution. Co-defendant Arthur Grimes will be sentenced on Jan. 13.

Ft. Lauderdale, Florida: Tax preparer Jean Volvick Moise, 39, has been sentenced to three years in prison for filing false income tax returns.

Moise prepared false returns for clients to inflate refunds. He prepared returns which included, among other things, false dependents, false 1099 withholdings, false educational credits and false Schedule C expenses, often for businesses which did not exist. Moise’s fee was larger than the typical one charged by a tax preparer.

Moise filed hundreds of false returns that caused the IRS to issue more than $574,000 in fraudulent refunds.

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Accounting

Accounting in 2025: The year ahead in numbers

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With 2025 almost upon us, it’s worth thinking about what the new year will bring, and what accounting firms expect their next 12 months to look like.

With that in mind, Accounting Today conducted its annual Year Ahead survey in the late fall to find out firms’ expectations for 2025, including their growth expectations, their hiring plans, their growth expectations, how they think tax season will play out and much more. The overall theme: Thing are going well, but there are elements of friction holding them back, particularly when it comes to moving to more of a focus on advisory services.

You can see the full report here; a selection of key data points are presented below.

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Accounting

On the move: Withum marks over a decade of Withum Week of Caring

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Citrin Cooperman appoints CIO; PKF O’Connor Davies opens new Fort Lauderdale office; and more news from across the profession.

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