Software Failures Can be Reasonable Cause for IRS Penalties – Houston Tax Attorneys


What one expects as data or information a business would commonly capture and maintain has changed dramatically over time. Readers who are older will appreciate this. The truth is that businesses tracked financial ins and outs and a few other items in the 1980s and leading up to the early 2000s.

It was the addition of the PC, Windows, and applications like spreadsheets in the early 1990s that allowed businesses to start tracking information in masse. Prior to this creating and maintaining data was hard. It was expensive. And it was largely a manual input process. And it was boring.

Armed with new tools, corporate accounting departments and then operation departments got to work on accumulating data. The data accumulation compounded over years—and then decades. The decades after the adoption of PCs saw the growth of software to manage and use the data that was created and stored. Software went from helpful to required. And we are not talking any software. We are talking about several discrete specialized software that produces varying outputs–all of which require specialized skills to know how to use it and how to evaluate whether its outputs are correct.

It is this backdrop that poses the question as to what happens when the software does not work? What happens when that software fails to perform as expected? Does reliance on faulty software provide reasonable cause to abate penalties for unfiled information returns? The recent case of Dealers Auto Auction of Southwest LLC v. Commissioner, T.C. Memo. 2025-38, provides an opportunity to consider these questions.

Facts & Procedural History

The taxpayer in this case was a business that operates an automobile auction house in Phoenix, Arizona. In the normal course of business, the business regularly received cash payments exceeding $10,000. This triggered Form 8300 reporting requirements under the tax code.

This tax dispute wasn’t the business’ first experience with Form 8300 compliance issues. In 2014, the business had failed to file some Information Reporting Returns resulting in the IRS Sections 6721 and 6722 penalties in the amount of $21,200.

In response to these earlier failures, the business purchased AuctionMaster software from Integrated Auction Solutions (“IAS”). This softare included modules for specialized reporting, including Form 8300 preparation. According to promotional materials, the software “has been setup [sic], tested in audits and approved for use by the IRS.”

For 2016, the software generated 116 Forms 8300 for the business, but the IRS determined that the business should have filed an additional 266 Forms 8300. The IRS assessed penalties totaling $118,140 for these failures. The business did not realize its noncompliance until the IRS examination began. After learning of the failures, the company implemented corrective actions, clarified its filing obligations with the IRS, and implemented new internal controls.

In November 2019, the IRS sent the business a Notice of Federal Tax Lien Filing. The business requested a Collection Due Process hearing, challenging its underlying liability and seeking reasonable cause abatement of the penalties. For the CDP hearing, the Appeals Officer rejected the reasonable cause argument and the business filed its petition with the U.S. Tax Court for review.

Section 6050I Information Return Requirements

To understand this case, we have to start with the information return requirements.

Section 6050I of the tax code sets out information reporting requirements for large cash transactions. This requires any person who, in connection with their trade or business, receives more than $10,000 in cash in a single transaction (or two or more related transactions) to file an information return with the IRS.

The purpose behind this requirement is to help the government track large cash transactions that might otherwise escape detection. Cash transactions, by their nature, leave less of a paper trail than electronic payments or checks, making them potentially more susceptible to use in money laundering, tax evasion, or other financial crimes.

The information return filed with the IRS must identify the person from whom the cash was received, the amount received, the date and nature of the transaction, and other information as required by regulations. This information return is submitted on Form 8300.

Additionally, under Section 6050I(e), the business receiving the cash must furnish a written statement to each identified person containing specific information reported to the IRS. This statement must be furnished on or before January 31 of the year following the calendar year in which the cash was received.

What Are the Penalties for Form 8300 Filing Failures?

As with anything that is a “requirement” for tax purposes, there are penalties for failing to satisfy the requirement.

As it did in this case, the IRS can impose penalties for failures to file required information returns under Sections 6721 and 6722. These penalties apply to various information returns, including Forms 8300 required under Section 6050I.

Section 6721 imposes a penalty of $250 for each Form 8300 a business fails to file, not to exceed $3 million for any calendar year. This amount is subject to inflation adjustments. If a business corrects the failure within 30 days, the penalty is reduced to $50 per failure.

Similarly, Section 6722 imposes a $250 penalty for each payee statement a business fails to furnish, also capped at $3 million annually and subject to inflation adjustments. The penalty is likewise reduced to $50 per failure if corrected within 30 days.

In this case, the business had penalties assessed for $68,640 for 264 Forms 8300 that were more than 30 days late, $100 for 2 Forms 8300 less than 30 days late, $16,380 for 63 delinquent dealer notifications, and $33,020 for 127 delinquent “Runner” notifications, totaling $118,140.

When Does Reasonable Cause Apply to Information Return Penalties?

Congress has recognized that penalties are not always appropriate. For most civil tax penalties, Congress has provided a reasonable cause defense that can be used to avoid the imposition of penalties. Congress made this a discretionary provision that the IRS can apply or not apply.

As relevant for this article, businesses can avoid these penalties if they can demonstrate that the failure to file or furnish was due to reasonable cause and not willful neglect. Under Treasury Regulation § 301.6724-1(a)(2), a taxpayer has reasonable cause when either:

  1. There are significant mitigating factors with respect to the failure, or
  2. The failure arose from events beyond the filer’s control.

Additionally, the filer must also establish that it acted in a responsible manner both before and after the failure occurred.

Significant mitigating factors generally refer to first-time offenses, including situations where the filer was never previously required to file that particular type of return or has an established history of compliance. The business in this case could not claim these mitigating factors because it had previously filed these forms and had prior compliance failures.

Events beyond the filer’s control can include unavailability of business records, economic hardship related to filing on magnetic media, certain actions by the IRS, actions of an agent, or actions of the payee or another person providing necessary information.

The regulation does not specifically address software failures, but the IRS’s Internal Revenue Manual (its policy manual) acknowledges that failures related to software and hardware can constitute events beyond a filer’s control for purposes of the reasonable cause defense.

Can Software Malfunctions Provide Reasonable Cause?

The central issue in this case was whether reliance on allegedly malfunctioning software could constitute reasonable cause for failing to file information returns. This raises an important question for businesses that increasingly depend on specialized software for tax advice and compliance.

The tax court distinguished this situation from cases involving accuracy-related penalties, where it has generally held that “software does not constitute professional advice” for reasonable cause purposes. This is the so-called “turbo tax” defense that the court has rejected. The court noted that reliance on software is not available as a reasonable cause defense when the taxpayer fails to input correct information, citing Bunney v. Commissioner.

However, the tax court suggested that a software malfunction could potentially qualify as a failure beyond the filer’s control when the filer used the software correctly. The court acknowledged that Treasury Regulation § 301.6724-1(c)(1) does not preclude finding that a software malfunction could constitute reasonable cause.

The tax court also rejected the IRS’s argument that the duty to file information returns is non-delegable under United States v. Boyle–which is the leading court case that sets out the reasonable cause defense. The court noted that Boyle does not preclude the application of reasonable cause when a filer is misadvised about the need to file a return. The business here wasn’t arguing that it delegated its filing obligation to the software, but rather that the software failed to notify it that returns needed to be filed.

Why Was There No Reasonable Cause Here?

Despite the court’s openness to the possibility that software failures could constitute reasonable cause, the court concluded that the business here did not qualify for reasonable cause for two key reasons.

First, the business failed to establish that the software actually malfunctioned. The record was unclear about how the software allegedly failed. The instructions suggested the software prepared Forms 8300 for printing, but the business claimed the software filed the forms automatically. The court could not determine whether the supposed failure was a failure to create the required forms or a failure to file them. Communications between the busienss and IAS (the software maker) mentioned “improved” features in a software update, but nothing in the record established that the software was failing to perform as intended.

Second, the business failed to demonstrate responsible behavior before and after the failure. The court noted that the business did not establish that it was correctly using the software or that data was being entered correctly. The record provided no insight into the business’s installation, training, or use of the software.

Moreover, the business did not establish that it took reasonable steps to foster compliance. The significant drop in the number of Forms 8300 generated by the software in 2016 (116) compared to the required filings in 2014 (at least 212) should have alerted the company that something was wrong. The court noted that the business offered no explanation for why this reduction would have appeared reasonable.

The Takeaway

This case shows that while software failures may potentially constitute reasonable cause for penalty abatement, businesses must do more than simply blame the software when things go wrong. To establish reasonable cause based on software failures, businesses must document how the software was supposed to work, how it actually worked, and what steps they took to ensure compliance despite the failure. This puts the focus on gathering information after the tax compliance problem is discovered to document the “why” for the compliance problem that had already occurred. Creating and keeping these post-event records should be the focus.

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The tax code provides specific rules for when taxpayers can claim deductions for losses. These are rules enacted by Congress.

There are other so-called “judicial doctrines” that allow the courts to override the rules set by Congress. There are several of these that frequently come up in tax disputes, such as the economic substance doctrine (which was codified into law), the step transaction doctrine, etc. We have covered many of these doctrines in prior articles. We have not addressed the public policy doctrine.

The “public policy doctrine” allows courts to deny tax deductions that would otherwise be perfectly legal under the tax code when allowing such deductions would “frustrate” public policy.

The U.S. Tax Court recently applied this doctrine in Hampton v. Commissioner, T.C. Memo. 2025-32, to disallow a tax loss when the government seized assets of a business for the wrongdoing of the owner. This gets into issues of separation of powers, and how far the courts can go in overriding the rules set by Congress.

Facts & Procedural History

The taxpayer in this case was a stock broker. He operated as an S corporation, and was 100% owner of the S corporation.

In 2009, the taxpayer worked out an arrangement with his high school friend who had been appointed as the deputy treasurer of the State of Ohio. The arrangement involved the deputy treasurer directing trading business from the State of Ohio to the taxpayer, with the taxpayer sharing portions of his commissions with the deputy treasurer and two associates. The payments were aledged to have been disguised as legal fees or business loans. The taxpayer received approximately $3.2 million in commissions from these trades and paid about $524,000 to the conspirators.

In 2013, the taxpayer pleaded guilty to charges of bribery, fraud, and money laundering. In 2014, he was sentenced to 45 months in prison and ordered to forfeit approximately $2.2 million. In 2016, while he was incarcerated, the U.S. Marshals Service seized $1,182,543.71 in funds from seven bank accounts held in the name of either the taxpayer or his S corporation.

On its 2016 Form 1120S, the S corporation claimed a deduction of $855,882 for the forfeiture of its seized accounts. As the S corporation’s sole shareholder, the taxpayer reported this loss on his individual tax return. The IRS audited the tax return and disallowed the deduction for the tax loss. The taxpayer filed a petition with the tax court for review.

About the Public Policy Doctrine

The public policy doctrine is a judicial doctrine the courts have cited for denying tax deductions that would “frustrate sharply defined national or state policies proscribing particular types of conduct, evidenced by some governmental declaration thereof.” This principle was articulated by the Supreme Court in Tank Truck Rentals, Inc. v. Commissioner, 356 U.S. 30, 33-34 (1958).

This is not a rule created by Congress through legislation. Instead, it was developed by judges who decided that some tax deductions, though technically allowed by the tax code, should nevertheless be denied on public policy grounds. This represents a significant judicial encroachment on what would normally be the legislative domain of determining which deductions are allowable.

The doctrine is particularly applicable to tax penalties imposed by the government–in addition to income tax due resulting from the denial of tax deductions. As the Supreme Court explained, the “[d]eduction of fines and penalties uniformly has been held to frustrate state policy in severe and direct fashion by reducing the ‘sting’ of the penalty prescribed by the state legislature.” The underlying rationale is that allowing a tax deduction for a government-imposed penalty would effectively reduce the financial impact of that penalty, thereby undermining its deterrent effect.

How Does the Public Policy Doctrine Override Section 165?

Section 165(a) of the tax code allows a deduction for “any loss sustained during the taxable year and not compensated for by insurance or otherwise.” For individual taxpayers, the deduction is limited to losses incurred in a trade or business, in transactions entered into for profit, or in certain cases of casualty or theft. Notably, the text of Section 165 contains no exception for losses resulting from criminal forfeitures or other penalties.

In 1969, Congress partially codified the public policy doctrine by amending Section 162 of the tax code (which is the general provision that allows for business tax deductions) to explicitly disallow deductions for fines and penalties paid to a government for violation of law. However, Congress did not make similar amendments to Section 165 (which is the provision for deducting tax losses). This raises the question: Did Congress intend to limit the public policy doctrine to Section 162 deductions, leaving Section 165 free from such judicial restrictions?

The courts have not followed this distinction. The courts have applied the public policy doctrine to Section 165 deductions. For example, the Federal Circuit did so in Nacchio v. United States, 824 F.3d 1370, 1374 (Fed. Cir. 2016). In that case, the court explicitly stated that “§165 is subject to a ‘frustration of public policy’ doctrine.”

When Can Courts Override the Plain Language of the Tax Code?

How far courts are willing to go and should they be allowed to go in applying the public policy doctrine–even when doing so requires overriding the plain language of the tax code?

Under a strict reading of Section 165 and the S corporation flow-through rules under Section 1366, the taxpayer here would appear to be entitled to deduct his share of the S corporation’s loss from the asset forfeiture (there was an assignment issue for assigning income thath the court didn’t get to, which may also have been a problem had the court gotten to that issue–but that is beyond the scope of this article).

Section 165 allows deductions for “any loss” with certain limitations that don’t explicitly exclude criminal forfeitures. Section 1366(a) provides that an S corporation shareholder “shall take into account” his pro rata share of the corporation’s income or loss. Nothing in the text of either provision suggests an exception for losses resulting from criminal activity.

Yet the tax court determined that the public policy doctrine overrode these statutory provisions. The court held that even if the S corporation was entitled to claim a deduction (a question the court did not decide), the taxpayer as an individual was barred by the public policy doctrine from reporting his 100% passthrough share of the S corporation’s resulting loss on his individual return.

The court’s rationale was that allowing the taxpayer to d…

The court’s rationale was that allowing the taxpayer to deduct the loss would frustrate the sharply defined policy against conspiring to commit offenses against the United States. The taxpayer was the Purported wrongdoer, and the S corporation’s assets were somehow seized as part of a penalty for his wrongdoing. The court did not get into how the denial of a deduction is not a tax penalty, and the code already provides for tax penalties–no doubt which also applied.

Thus, apparently the taxpayer should be double penalized–with a tax penalty (probably more than one) and then again by the loss of his tax deduction. According to the court, allowing the taxpayer a deduction would unquestionably reduce the “sting” of the penalty (which a forfeiture is not a penalty), regardless of what the tax code actually says about such tax deductions.

How Far Can Courts Extend the Public Policy Doctrine?

The tax court emphasized that the public policy doctrine is not constrained by formalistic distinctions between legal entities. This is similar to the rules that apply when a taxpayer transfers assets to a spouse to avoid IRS collections. The court cited Holmes Enterprises, Inc. v. Commissioner, 69 T.C. 114 (1977), where a corporation claimed a deduction for the criminal forfeiture of a car it owned after its sole owner and president was convicted on illegal drug charges.

In Holmes, the tax court concluded that although the corporation was a “separate, taxable entity, distinct from its employee,” the public policy doctrine forbade it from claiming a deduction because it was not a “wholly innocent bystander.” Due to the convicted person’s role as the corporation’s sole owner and president, the corporation “knew of and fully consented to the illegal use of its automobile.”

This reasoning shows how courts have expanded the public policy doctrine to deny deductions not just to convicted individuals, but also to closely related entities, even when those entities themselves haven’t been charged with any crime. This judicial expansion extends the doctrine well beyond what Congress explicitly codified in Section 162(f).

Can a Taxpayer Challenge Judicial Overreach Through a Tax Deduction?

The taxpayer in this case argued that the application of the public policy doctrine should be limited because the United States’ seizure of the S corp’s assets violated due process and was “over-zealous” given that the S corp was not the wrongdoer. However, the tax court found no legal impropriety in the seizure of the S corp’s assets to satisfy the taxpayer’s forfeiture liability.

The court relied on the Sixth Circuit’s decision in United States v. Parenteau, 647 F. App’x 593 (6th Cir. 2016), which held that a corporation wholly owned by an individual convicted of a criminal conspiracy was not a person “other than the defendant” for purposes of forfeiture proceedings. The Sixth Circuit cited relevant factors including that the defendant wholly owned and controlled the corporation, that the corporation did not follow corporate formalities, and that the defendant used the corporation’s property in his criminal scheme.

By analogy, the tax court concluded that the S corporation in this case was not separate from the taxpayer as an individual for purposes of the substitute forfeiture provisions. The taxpayer wholly owned and controlled the S corp, offered minimal evidence that corporate formalities were followed, and the S corp’s sole source of business income was the commissions generated by the taxpayer that were “assigned” to the S corp—the very commissions that led to the criminal indictment, plea, and forfeiture. This is consistent with the court’s prior rulings that apply various judicial doctrines to S corporations.

Is There Any Limit to Judicial Override of Tax Code Provisions?

The tax court also rejected the taxpayer’s argument that the public policy doctrine’s application should be affected by alleged illegality or over-zealousness on the government’s part in seizing the assets. Both the Fourth Circuit and the tax court have previously indicated that the alleged illegality of a criminal forfeiture need not prevent the public policy doctrine from disallowing a deduction for the forfeited property.

In Hackworth v. Commissioner, 155 F. App’x 627, 632 (4th Cir. 2005), the Fourth Circuit stated: “If the taxpayers believe that the forfeiture was invalid, the proper remedy is for them to sue the [relevant government unit] and seek return of the funds [rather than claim a tax deduction].” Similarly, in the tax court’s decision in Hackworth, the court stated: “This Court lacks jurisdiction over [the taxpayers’] collateral attack on the forfeiture.”

This principle further demonstrates the power of the public policy doctrine as a judicial override of tax code provisions. Even if a taxpayer believes that a forfeiture was illegal or improper, courts will not allow them to deduct the loss under Section 165. Instead, they must challenge the forfeiture directly in another forum—a requirement found nowhere in the text of the tax code itself.

The Takeaway

This case shows how the judge-made public policy doctrine can override explicit provisions of the tax code. Despite clear statutory language allowing deductions for business losses and requiring S corporation shareholders to report their share of corporate losses, the tax court denied the taxpayer’s deduction based on a doctrine created by judges, not legislators.

The tax law as written by Congress can be trumped by judicial doctrines when courts determine that public policy would be frustrated by allowing certain deductions. Taxpayers facing criminal forfeitures should understand that the public policy doctrine enables courts to disallow deductions that would otherwise be permitted under a plain reading of the tax code, particularly when there is a direct connection between criminal activity and the forfeited assets.

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