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In a 2019 U.S. Tax Court case, Palmolive Building Investors, LLC v. Commissioner, 152 T.C. No. 4, (2019) (Palmolive II), the Tax Court held that both penalties determined by the Revenue Agent in a tax audit and additional penalties later determined  by an Appeals Officer in the IRS Independent Office of Appeals met the written approval requirements of I.R.C. § 6751; thus making Palmolive Building Investors, LLC (Palmolive) a two-time loser. Palmolive was initially in Tax Court in 2017 (Palmolive I) over a disallowed charitable deduction for a façade easement.  As the owner of a historical building in Chicago, it had donated a façade easement to a conservation organization and took a large charitable deduction for the easement. In addition to questioning the $33,410,000 valuation of the easement, the IRS argued that the mortgages on the building limited the easement’s protection in perpetuity. The Tax Court agreed and concluded that the façade easement was not protected in perpetuity and therefore failed to qualify for a charitable deduction under I.R.C. § 170(h)(5)(A).

Following the disallowance in Palmolive I, the taxpayer returned to the Tax Court to dispute whether the penalties assessed by the IRS complied with the provisions of IRC Section 6751(b)(1).  During a tax audit, a Revenue Agent had asserted in a 30-day letter that Palmolive was responsible for a 40% penalty for a gross valuation misstatement and a 20% negligence penalty. These two penalties were approved on Form 5701 by the Revenue Agent’s supervisor. Subsequently, a 60-day letter was issued. The taxpayer took its case to the IRS Office of Appeals. The Appeals Officer assigned to the case proposed four penalties: the two assessed by the Revenue Agent and the Substantial Understatement and Substantial Valuation Misstatement penalties. The Appeals Officer’s immediate supervisor approved all of these penalties on Form 5402-c. In Tax Court, Palmolive argued that the initial determination of penalties was made by the Revenue Agent who did not assert the Substantial Understatement and Substantial Valuation Misstatement penalties; therefore the penalties asserted by the Appeals Officer were not approved as part of the first determination of the penalties.

In examining the validity of the penalty assessments, the court cited I.R.C. § 6751(b)(1) which states that penalties can only be assessed when the initial determination of such penalties are approved in writing by the immediate supervisor of the person making the determination. The court also pointed out that the Congressional motive behind enacting this provision was to make sure penalties were not used as bargaining chips. The court first noted that all penalties were approved in writing. The next issue was what defines an “initial determination” for the purposes if I.R.C. § 6751(b)(1). The court held that the initial determination is when the penalties were first communicated to the taxpayer. The court stated that the Revenue Agent’s 2008 mailing of the 30-day letter was the date of the initial determination and the Appeals Officer’s 2014 issuance of the Notice of Final Partnership Administrate Adjustment are both initial determinations. Since the IRS forms were signed by the respective supervisors prior to the time of the initial determinations, the penalties met the requirements of Section 6751(b) (1).

An article this summer in Tax Notes Today examined the United States government’s ability to tax cryptocurrencies. The article came days before cryptocurrencies saw another bullish run in which the value of a single unit of bitcoin once again passed $10,000. Additionally, the article references the comments of IRS special agent Gary Alford who stated the IRS is ready to enforce the taxation of a U.S. taxpayer’s gains from cryptocurrencies. Special agent Alford argues that the public’s familiarity with cryptocurrencies will make it easier for the IRS to file criminal tax cases against some taxpayers who evade their tax reporting obligations. Given this new warning from Alford, criminal tax attorneys need to be prepared to defend their clients who hold cryptocurrencies.

In Notice 2014-12, the IRS wrote that it considers cryptocurrencies to be property and, as such, the disposition or exchange of cryptocurrencies will be taxable. A clear example of a taxable event is where a bitcoin holder exchanges a single bitcoin (or any fraction thereof) for fiat currency. Fiat currency is understood to be currency backed by a national government, e.g. the Euro or U.S. dollar.

A tricky issue for taxpayers may be determining the adjusted basis of their holdings in a cryptocurrency to determine realized gain. Sometimes a single unit of cryptocurrency may have been involved in multiple exchanges and transactions before the taxpayer finally reports to the IRS he or she holds the cryptocurrency. The taxpayer is placed in the difficult task of proving the correct basis of the cryptocurrency. A taxpayer who provides an inaccurate basis is likely to be subject to penalties in addition to the amount in taxes owed.

In Greek mythology, King Sisyphus is punished by the gods and forced to roll a huge boulder up a hill only for it to roll down as it nears the top. No matter how much effort Sisyphus puts into attempting to push the boulder over the crest of the hill, it always come tumbling back down. He is doomed to push the boulder up the hill for all eternity. Sometimes collecting payroll taxes can be a “Sisyphean task” for the IRS. At least, that is what the 11th Court of Appeals wrote in a recent decision.

United States v. Askins & Miller Orthopedics, involved a private medical practice which refused to pay payroll taxes. The IRS first tried to negotiate an installment agreement with the medical practice’s business owners, but the business owners would ultimately renege on any agreement. Then the IRS issued a tax levy on property held by the medical practice in various entities, but the business owners would simply shift property to new entities out of reach of the power of the levies. Believing it was out of options, the IRS requested a permanent injunction from the district court to compel the taxpayers to perform and pay their employment taxes now and into the future.

The district court rejected the IRS request because the court argued that the IRS had yet to suffer irreparable harm. The district court reasoned that the IRS could still sue for monetary damages once the taxpayers again failed to pay their employment taxes. This is in spite of the fact that the district court conceded that the taxpayers exhibited a pattern of unlawful conduct likely to persist. In other words, the taxpayers would continue to find ways to not pay their taxes.

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A 2017 case is a stark $300,000 reminder that the IRS is not bound by statements made by its employees, such as Revenue Officers. Tommy Weder was a responsible officer of a corporation which failed to pay its payroll taxes, and as a result, he was assessed a trust fund recovery penalty (TFRP) pursuant to IRC Section 6672. After he paid the $300,000, he filed suit in federal district court in Oklahoma requesting a refund. His theory was that the company had paid $300,000 towards the trust fund taxes, and that, therefore, his personal liability was reduced by that amount. In most cases, a taxpayer must pay any tax in full (not just a portion) before he or she can file a suit for a refund. However, under the so-called Flora rule, payroll taxes are divisible taxes, therefore, the taxpayer must only pay the tax due for one employee for one quarter.

The IRS took the position that the payment was not properly designated toward the trust fund, and that it was therefore entitled to, and did, apply the payment towards non-trust fund taxes owed by the company, which of course doesn’t reduce the trust fund recovery penalty. Weder didn’t dispute that there hadn’t been a written designation of tax. The payment had been made through the IRS’ EFTS system, and there was no designation. Weder argued, however, that the Revenue Officer that had been assigned to collection had met with representatives of the company, including its CPA, and that the Revenue Officer had demanded that the payment be made through EFTPS, and represented that the payment would be applied to the trust fund taxes.

The court ruled that absent a WRITTEN designation by the company, the IRS was free to apply the payment in the “best interest” of the government. The Court relied on Rev. Proc. 2002-26, which provides that absent written directions, the IRS “will apply payments to periods in the order of priority that the Service determines will serve the Service’s best interest.” It pointed out that prior to Rev. Proc. 2002-26 being promulgated, the prior IRS guidance was contained in Rev. Rul. 73-2. CB 43. That Revenue ruling only required that taxpayers give “directions.”

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Taxpayers and their accountants sometimes believe that tax evasion, especially criminal tax evasion, is reserved for “the big guys”. While the IRS likes to go after the big fish, even the minnows can get caught in the net. Take the case of Orlando Cardoso. He was a manager of the scallop division at an unnamed seafood processor in New Bedford, Massachusetts.

It appears from the indictment that something fishy was going on. Cardoso was receiving payments from his company’s supplier in 2012 and 2013. He deposited those payments, which came in the form of cash and checks, in his Bank of America account. Perhaps not surprisingly, he didn’t report those payments on his income tax returns.

The reasons why he didn’t report the payments is undisclosed, but any one or a combination of factors could have been at play.

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In a recent tax case, the U.S. Tax Court concluded that the IRS statutory Notice of Deficiency (a.k.a. “90-day letter”) issued more than three years after the tax return was filed was invalid, despite the omission of income from foreign assets. The taxpayer had timely filed his federal income tax returns for the years at issue, but he did not report income earned on a foreign account he held. The years at issue were 2006, 2007, 2008, and 2009. To obtain information related to the account of the taxpayer, and other similarly situated persons, the IRS had served a John Doe summons. The John Doe summons was resolved on November 16, 2010. However, the IRS did not issue a statutory Notice of Deficiency until December 8, 2014.

The taxpayer in this case timely filed his returns, which started the statute of limitations period. Absent circumstances that would toll or fail to initiate the statute of limitations, the IRS does not have an indefinite amount of time to assess tax. The IRS must issue timely Notices of Deficiencies and failure to do so can benefit the taxpayer.

When is a Notice of Deficiency Timely?

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The IRS has issued a notice stating it will begin the process of revoking passports of individuals with “seriously delinquent tax debts.” Seriously delinquent tax debts are those totaling more than $50,000 indexed for inflation. According to the Internal Revenue Manual the threshold is now $51,000. The amount includes not just the tax, but penalties and interest as well. However, the statute refers to “assessed” liabilities, and there are many instances where the IRS doesn’t assess all of the accrued interest and penalties so it is possible to owe the IRS more than $50,000, and still not meet the threshold. Notably, FBAR penalties are not counted towards the threshold.

Revocation of passports is not new. It was authorized by Congress in December of 2015 pursuant to new Internal Revenue Code Section 7345. However, the IRS has not implemented the program until now.

Although most tax attorneys and tax accountants refer to the IRS revoking passports, what actually happens is the IRS sends a certification to the State Department, and the State Department will take action to revoke the passport. The IRS will notify taxpayers in writing at the time of certification using IRS Notice CP 508C. The IRS will send the notice by regular mail to the taxpayer’s last known address. Since they will not be sending it by certified mail, there will be no way to prove that the IRS didn’t send it in cases where the notice is not received.

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