Privilege and Non-Disclosure Archives

Privilege and Non-Disclosure

AI platforms and privilege: Tax departments should be wary about what they share

by Susan E. Ryba and Matthew J. Blaney | Mar 23, 2026 | Court Procedure Matters, Privilege and Non-Disclosure, Significant Court Decision, Trial Courts

Today’s artificial intelligence (AI) platforms have shown impressive capabilities that keep evolving. As those capabilities improve, tax departments may be inclined to leverage AI’s analytical power. While this technology has led to incredible efficiencies, we’ve been warning in-house tax departments about which platforms they use and what information they share to avoid waiving privilege or creating documents that cannot be protected.

The US District Court for the Southern District of New York recently held that a criminal defendant’s communications with a publicly open AI platform were not protected by attorney-client privilege nor the work product doctrine. United States v. Heppner, No. 1:25-cr-00503-JSR (S.D.N.Y. Feb. 17, 2026).

In Heppner, the defendant transmitted confidential information to a public AI system and generated various documents that incorporated the information. The district court concluded that the documents created were not protected by attorney-client privilege nor the work product doctrine. The AI platform was a public and open system that did not provide confidentiality, the documents created by the AI platform were not prepared by or at the direction of counsel (in fact, counsel had no idea the client was using AI), and documents (regardless if created by AI or other means) can never be cloaked with privilege simply because they are later sent to a lawyer.

Practice point:

While the facts of Heppner are probably distinguishable from how tax departments typically use AI platforms, the case serves as a reminder for tax professionals to have good hygiene when using them. All in-house tax professionals should exercise caution when inputting confidential information into AI platforms and, where possible, rely on closed, internal AI systems that are only accessible by relevant persons within their corporation. Even then, Heppner makes clear that AI platforms are not lawyers, and disclosures of privileged information to such platforms risk waiving that privilege.

Given this risk, tax professionals should use great caution when using AI for sensitive legal issues. At a minimum:

Do not input any sensitive, confidential, or privileged information into publicly open AI systems.

Remember that AI is not a lawyer, so asking AI legal questions is not the same as asking a lawyer for legal advice.

For tax issues that are likely to result in a contentious audit or litigation, work with in-house or outside counsel to establish best practices on AI use to maximize attorney-client privilege and work product protection.

Supreme Court Punts on Attorney-Client Privilege Question

by Kevin Spencer, Sarah M. Raben and McDermott Will & Schulte | Feb 2, 2023 | Appellate Courts, Court Procedure Matters, IRS Audits, Privilege and Non-Disclosure, Trial Courts

In a surprising move, the Supreme Court of the United States (SCOTUS) dismissed a dispute involving the proper test to apply when determining whether an unnamed law firm’s mixed bag of communications involving both legal advice and discussions of tax preparation was privilege. The dismissal came less than two weeks after oral arguments, with SCOTUS stating that “[t]he writ of certiorari is dismissed as improvidently granted” (commonly known as a “DIG,” which infrequently happens when SCOTUS determines there is no conflict warranting review, one or both parties have changed their position, or no consensus can be reached by the Justices and dismissal is preferable to fractured opinions with no controlling rationale).

BACKGROUND

The law firm and an unnamed company were each served with subpoenas for documents and communication related to a criminal investigation. Both produced some documents but withheld others on the grounds of attorney-client privilege and the work-product doctrine. The government moved to compel production, which the district court granted in part, explaining that the documents were not protected by any privilege, and they were discoverable under the crime-fraud exception. The company and law firm continued to withhold the documents, and the government filed motions to hold them in contempt. The district court ruled that certain dual-purpose communications were not privileged because the “primary purpose” of the documents was to obtain tax advice, not legal advice. On appeal to the US Court of Appeals for the Ninth Circuit, the law firm and the company argued that the court should have relied on a broader, “because of” test, not the “primary purpose” test. The Ninth Circuit disagreed and concluded that the “primary purpose” test governs, and the primary purpose of the communications was tax advice. SCOTUS granted certiorari in October 2022.

SUPREME COURT

In its brief, the law firm asked SCOTUS to adopt a more expansive “significant purpose” test, which was applied by the US Court of Appeals for the District of Columbia Circuit in In re Kellogg Brown & Root, Inc. The law firm argued that the test applied in Kellogg “appropriately protects attorney-client dual purpose communications” and that the test “asks a single question that arises directly from the long-established test for attorney-client privilege: whether a client is seeking or obtaining confidential legal advice from his or her lawyer.”

The government argued that courts consistently emphasize the need to construe the attorney-client privilege narrowly and that the primary or predominant purpose test “thus molds the scope of the privilege to its purpose of encouraging effective legal advice, while avoiding sweeping in communications predominantly about a nonlegal matter.”

During oral argument, the Justices seemed skeptical of a need to change the test and expressed some confusion as to how any privilege analysis would change from a practice perspective. Justice Kagan invoked the saying “if it ain’t broke, don’t fix it.” Shortly thereafter, SCOTUS issued the DIG.

Practice Point: More [...]

Continue Reading

Stats Show Active Tax Whistleblower Caseload

by Kevin Spencer and Le Chen | Jan 7, 2020 | IRS Guidance, Privilege and Non-Disclosure, Uncategorized

On January 6, 2020, the IRS Whistleblower Office released its annual report to Congress. The Office reported that it collected $616.8 million in fiscal year 2019 as a result of information provided by whistleblowers, out of which $120.3 million was paid out as whistleblower awards, for net collections of $496.5 million. This is a decrease from the $1.13 billion in net collections in fiscal year 2018 (which has been described as an outlier year), but an increase from the $156.6 million in net collections in fiscal year 2017. A total of 3,640 whistleblowers filed claims in fiscal year 2019, including 282 whistleblowers from outside of the United States.

Practice Point: Whistleblower actions are a good reminder to make sure that your privileged and confidential tax information remains in the hands and minds of only those employees and officers who have a need to know. A disgruntled or terminated employee may take the opportunity to play the “whistleblower lottery,” removing sensitive and privileged material and handing it over to the IRS. With the start of the new year, it’s a worthwhile investment of time and resources to make sure your sensitive tax strategies and information are stored and protected.

Big Change for Witness Privilege in House Investigations

by Llewelyn Engel and McDermott Will & Emery | Feb 15, 2019 | Court Procedure Matters, Privilege and Non-Disclosure, Uncategorized

On Jan. 25, 2019, U.S. House of Representatives Rules Committee Chairman James P. McGovern, D-Mass., issued regulations governing staff deposition authority in the 116th Congress, pursuant to his authority under H. Res. 6. In passing H. Res. 6, the newly empowered House Democratic majority drastically increased House committees’ investigative power by allowing committee staff to conduct depositions without members present — a stark departure from precedent. This change was a dramatic first step in the House Democratic majority’s efforts to ramp up oversight of both the executive branch and the private sector.

Access the full article.

Kovel Protections Upheld | Government Loses Aggressive Arguments for Waiver of Privilege for Controversy Advice

by McDermott Will & Emery | Nov 12, 2018 | Court Procedure Matters, IRS Guidance, Privilege and Non-Disclosure, Trial Courts, Uncategorized

On October 27, the US District Court for the District of Minnesota issued an opinion in United States v. Adams, No. 0:17-cr-00064-DWF-KMM (D. Minn. Oct. 27, 2018), addressing attorney-client privilege issues relevant to accountants working alongside tax attorneys. The court adopted a narrow, nuanced view of the waiver that applies when the taxpayer discloses an accountant’s work to the Internal Revenue Service (IRS) by filing an amended return.

In Adams, the taxpayer is facing a 17 count superseding indictment in which the government alleges he spearheaded a scheme to defraud investors in two companies and to embezzle corporate funds for his personal benefit. In late 2017, the government added three counts of tax evasion to the indictment, alleging that amended returns the taxpayer filed in late 2011 for the 2008, 2009 and 2010 tax years were willfully false under IRC § 7206(1).

The addition of the tax evasion charges is significant for the government’s arguments for waiver of privilege and work-product protection. It appears that the taxpayer filed the amended returns at issue in late 2011 under advice of counsel, working with the taxpayer’s accountant under a Kovel arrangement. (We have previously discussed the scope of Kovel protections here.) In our experience, filing of amended returns in advance of a criminal investigation or trial is one potential strategy to demonstrate good faith and lack of criminal intent and, if combined with payment, amended returns may have the added benefit of reducing the tax loss at issue in a criminal case. Of course, every case is different, but it appears this may have been the strategy at work in Adams. (more…)

OVDP Ending September 28: Now Is the Time to Disclose

by McDermott Will & Emery | Aug 23, 2018 | IRS Audits, IRS Guidance, Privilege and Non-Disclosure, Uncategorized

Earlier this year, the Internal Revenue Service (IRS) announced the ending of the 2014 Offshore Voluntary Disclosure Program (OVDP), its formal amnesty program for taxpayers with previously undisclosed interests in foreign assets and financial accounts. The program deadline is September 28, 2018, and all submissions must be substantially completed by that deadline. Partial or “placeholder” submissions will not qualify. All requests for preclearance into the program must be submitted by Friday, August 24, 2018.

A number of other disclosure options will remain available after September 28, 2018, including the popular IRS streamlined compliance procedures. Regardless, taxpayers with potential questions or concerns regarding reporting of their foreign holdings should seek advice immediately in light of upcoming deadlines.

Expect Controversy in the Wake of Tax Reform

by Kevin Spencer and Robin L. Greenhouse | Feb 7, 2018 | IRS Audits, IRS Guidance, Privilege and Non-Disclosure, Tax Reform, Uncategorized

Tax reform is here to stay (at least for the foreseeable future). The Internal Revenue Service (IRS) may receive additional funds to implement the new tax law. With lowered tax rates, accelerated expensing and forced repatriation of foreign earnings comes an increased risk of an IRS audit. This brave new tax world has left so many questions that tax advisors’ phones have been ringing off the hooks! But as the end of the 2017 year and first quarter of 2018 dust settles, be mindful of the IRS audit to come. (more…)

Maintaining Confidentiality While Navigating Cross-Border Transactions

by McDermott Will & Emery and McDermott Will & Emery | Dec 14, 2017 | IRS Audits, IRS Guidance, Privilege and Non-Disclosure, Uncategorized

Today, taxing authorities across the globe, including the Internal Revenue Service (IRS), are increasing their efforts to gather and share sensitive taxpayer information, often aggressively seeking copies of tax advice, opinions and analysis prepared by counsel and other advisors. In some situations, tax advisors specifically draft their advice to be shared with third parties, but frequently the IRS seeks advice that was always intended to be confidential client communications—for example, drafts and emails containing unfinished analysis and unguarded commentary. Sharing this latter type of advice could be problematic for taxpayers because such advice could be used as a road map for examiners during an audit and may mislead the IRS regarding the strength or weakness of a taxpayer’s reporting positions.

Last month, we spoke to tax executives at Tax Executives Institute forums in Houston and Chicago about the IRS’s increased use of treaty requests to obtain US taxpayers’ documents and information from international tax authorities. (more…)

Tax Court Says IRS’s “Drift-Net” Argument to Expand Privilege Waiver Must Be Anchored in Principles

by Jeffrey M. Glassman, Kevin Spencer, Robin L. Greenhouse and Roger J. Jones | Nov 3, 2017 | Court Procedure Matters, IRS Audits, IRS Guidance, Privilege and Non-Disclosure, Trial Courts, Uncategorized

In Estate of Levine v. Commissioner, the US Tax Court (Tax Court) rejected an Internal Revenue Service (IRS) attempt to expand upon the privilege waiver principles set forth in AD Inv. 2000 Fund LLC v. Commissioner. As background, the Tax Court held in AD Investments that asserting a good-faith and reasonable-cause defense to penalties places a taxpayer’s state of mind at issue and can waive attorney-client privilege. We have previously covered how some courts have narrowly applied AD Investments.

In Estate of Levine, the IRS served a subpoena seeking all documents that an estate’s return preparer and his law firm had in their files for a more-than-ten-year period, beginning several years before the estate return was filed and ending more than four years after a notice of deficiency (i.e., which led to the Tax Court case) was issued. The law firm prepared the estate plan and the estate tax return in issue. The law firm represented the estate during the audit, and after the notice of deficiency was issued, the law firm was engaged to represent the estate in “pending litigation with the IRS.” (more…)

Tax Court Requires Specific Factual Showing of Harm for Whistleblower Anonymity

by McDermott Will & Emery and McDermott Will & Emery | Sep 28, 2017 | Privilege and Non-Disclosure, Trial Courts, Uncategorized

In two recent cases, the United States Tax Court (Tax Court) has explored the bounds of the anonymity protection afforded to potential whistleblowers under the court’s rules and other authorities. Tax Court Rule 345 relates to privacy protections for filings in whistleblower actions. Under paragraph (a), a whistleblower may move the court for permission to proceed anonymously. In order to proceed anonymously, the whistleblower must provide a sufficient, fact-specific basis for anonymity. Specifically, the Tax Court has held that “[a] whistleblower is permitted to proceed anonymously if the whistleblower presents a sufficient showing of harm that outweighs counterbalancing societal interest in knowing the whistleblower’s identity.” (Whistleblower 10949-13W v. Commissioner, T.C. Memo 2014-94, at 5). However, the balance of harm to societal interest may shift as the case progresses, thereby justifying disclosure after anonymity has been granted. See Tax Court Rule 345(b). (more…)

EDITOR IN CHIEF

STAY CONNECTED

TOPICS

ARCHIVES

RECENT POSTS