attorney-client privilege Archives

attorney-client privilege

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 [...]

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Fifth Circuit Rules that Law Firm Clients’ Identities Are Not Privileged

by Kevin Spencer and Le Chen | Apr 28, 2020 | Appellate Courts, IRS Appeals, Trial Courts, Uncategorized

In Taylor Lohmeyer Law Firm P.L.L.C. v. United States, No. 19-50506, the United States Court of Appeals for the Fifth Circuit held that a Texas-based estate and tax-planning law firm (Firm) could not invoke the attorney-client privilege against an Internal Revenue Service (IRS) summons seeking the identity of its clients.

According to an IRS revenue agent’s declaration submitted in support of the summons, the Firm became a target for IRS investigation following an audit of one of its clients, an individual who had used the Firm’s services to establish and operate various foreign accounts and entities, through which the individual had funneled millions of dollars of unreported income. The IRS issued a John Doe summons to the Firm seeking, amongst other things, the identities of other clients for whom it had established foreign accounts or entities.

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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…)

A 360-Degree View: September and October 2017

by McDermott Will & Emery | Oct 5, 2017 | Uncategorized

Wrapping Up September – and Looking Forward to October

Upcoming Tax Controversy Activities in October:

October 12, 2017: Cate Battin, Kristen Hazel, Britt Haxton, Jane May, Sandra McGill, Diann Smith and Elizabeth Chao are hosting and presenting at the inaugural Tax in the City® event in Seattle, Washington. They will cover topics such as attorney-client privilege and the ethics of social media (CLE/CPE), recent developments around US Tax Reform, and updates on state and local tax issues for Seattle and the surrounding areas.

October 25, 2017: Todd Welty and Lowell Yoder are speaking at the TEI 72nd Annual Conference in Toronto, Ontario, and will present “Repatriation: Strategy, Practice and the Road Ahead.”

November 2, 2017: Laura Gavioli, Kristen Hazel, Michael Louis, Cym Lowell, Damon Lyon, Denise Mudigere, Dave Noren, Kristina Novak, Andrew Roberson, Jay Singer, Mark Thomas and Michael Wilder are speaking at the TEI Global Tax Symposium in Houston, Texas, and covering the following topics: Multilateral Instruments & European Developments, Country by Country Reporting, Repatriation Strategies and the IRS Repatriation Campaign, Disclosures for Global Tax Strategies, and Treasury Center/Currency Issues. (more…)

Tax in the City® New York Event Success

by McDermott Will & Emery | Sep 26, 2017 | Court Procedure Matters, IRS Guidance, Privilege and Non-Disclosure, Tax Reform, Transfer Pricing Resource, Uncategorized

Female tax professionals gathered in McDermott Will & Emery’s New York office for an annual New York rendition of Tax in the City®: A Women’s Tax Roundtable on Thursday, September 14. Featuring a CLE/CPE presentation about Privilege and the Ethics of Social Media by Kristen Hazel and Robin Greenhouse, an update on tax reform by Sandra McGill and an overview of recent state and local tax news by Alysse McLoughlin, the event culminated in a networking reception over cocktails.

Topics covered at the event included:

Best practices for preserving attorney-client privilege and work product protection; strategies to prevent an inadvertent waiver.
Ethics of social media (think before you post).
Tax reform:
- Where are we now (framework to be issued week of September 25 and legislation sometime in October, possibly after budget).
- What could tax reform look like (e.g., reduced tax rate, one-time tax on unrepatriated foreign earnings, move to territorial tax with DRD and corresponding changes to foreign tax credit system, changes to IRS Subpart F, elimination of certain deductions and/or adjustments to the taxation of carried interests).
- What should taxpayers be thinking about (e.g., taking steps to best position your organization to proactively react to tax reform both now and when the reform measures become effective).
Status of certain tax regulations identified in Notice 2017-38 per mandate of EO 13789: Treasury provided recommendations to President Trump on September 18, 2017, and its report should be published sometime this month. We discussed possible change/revocation/deferred effective dates for regulations under Sections 367, 385 and 987 and steps taxpayers are taking today to address these regulations.
Partnership Update:
- New TEFRA rules are effective January 1, 2018: TEFRA partnership agreements should be reviewed; assess whether the agreement should be amended (or other agreements implemented) to address these new rules.
- Grecian Magnesite Mining: Tax Court held that gain derived by foreign person from disposition of its interest in a partnership engaged in US trade or business was treated as the disposition of a capital asset not as the disposition of the partner’s share of the underlying partnership assets and was not subject to US federal income tax as effectively connected income. It is unclear whether this case will be appealed.

State tax apportionment issues: We discussed the difficulty in establishing the proper level of reserves due to both the uncertainty in applying the statutory sourcing methods and the state taxing authorities’ ability to use their discretionary authority to revise the statutory sourcing methods.

We invite all tax professionals who identify as female to join Tax in the City®’s official LinkedIn group to continue the conversation and share tax developments in between events and meetings! Click here to join.

Established in 2014 by McDermott Will & Emery LLP, Tax in the City® is a discussion and networking group for women in tax that fosters collaboration and mentorship and facilitates in-person connections and roundtable events around the country. This New York edition of [...]

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The IRS Is Struck Down Again in Privilege Dispute

by McDermott Will & Emery and McDermott Will & Emery | Aug 11, 2017 | Court Procedure Matters, IRS Guidance, Privilege and Non-Disclosure, Trial Courts, Uncategorized

Courts continue to strike down the Internal Revenue Service (IRS) as it continues to test the bounds of the attorney-client privilege and work product doctrine through the issuance of improper summonses. In the last several years, the IRS has filed numerous summons enforcement proceedings related to the production of documents generally protected by the attorney-client privilege, tax-practitioner privilege, and/or work product doctrine. These summonses include overt requests for “tax advice” and “tax analysis,” which several courts have refused to enforce. For example, see Schaeffler v. United States, 806 F.3d 34 (2d Cir. 2015).

Once again, in United States v. Micro Cap KY Insurance Co., Inc. (Eastern District of Kentucky), a federal district court rejected the IRS’s arguments and refused to enforce an inappropriate summons. The opinion is available here. The IRS filed this enforcement proceeding seeking to compel the production of confidential communications between taxpayers and the lawyers that assisted them in forming a captive insurance company. After conducting an in camera review (where the judge privately reviewed the documents without admitting them in the record), the judge found the taxpayers had properly invoked privilege since each document “predominately involve[d] legal advice within the retention of [] counsel.”

The court also rejected the government’s argument that the attorney-client privilege was waived by raising a reasonable cause and reliance on counsel defense to penalties in the taxpayers’ case filed in Tax Court. Because the government’s argument was untimely, it was waived and rejected outright. The court, however, proceeded to explain how the argument also failed on its merits. (more…)

John Doe Intervenes in Virtual Currency Summons Enforcement Case

by Robin L. Greenhouse | Jul 21, 2017 | Court Procedure Matters, IRS Audits, IRS Guidance, Uncategorized

The Internal Revenue Service (IRS) has broad authority under Internal Revenue Code (IRC) Section 7602 to issue administrative summonses to taxpayers and third parties to gather information to ascertain the correctness of any return. If the IRS does not know the identity of the parties whose records are covered by the summons, the IRS may issue a “John Doe” summons only upon receipt of a court order. The court will issue the order if the IRS has satisfied the three criteria provided in IRC Section 7609(f):

The summons relates to the investigation of a particular person or ascertainable group or class of persons,
There is a reasonable basis for believing that such person or group or class of persons may fail or may have failed to comply with any provision of any internal revenue law, and
The information sought to be obtained from the examination of the records (and the identity of the person or persons with respect to whose liability the summons is issued) is not readily available from other sources.

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The Interplay Between Tax Planning and IP Planning

by Jennifer M. Mikulina and Kristen E. Hazel | Nov 4, 2016 | IRS Appeals, IRS Audits, Uncategorized

On November 3, 2016, we presented at the Chicago Tax Club’s symposium regarding tax planning and intellectual property (IP) planning within a multinational corporation. The presentation covered various areas, including the importance of coordination between IP and tax groups when engaging in IP planning, the differences in the IP arena and the tax arena with respect to IP matters that can impact tax planning positions, and tax planning with IP holding companies. From a tax controversy perspective, we discussed being prepared for an Internal Revenue Service (IRS) audit with respect to IP planning, with a focus on contemporaneous documentation to support the taxpayer’s position, having audit ready files (including adhering to document retention policies), reviewing IRS audit materials (e.g., International Practice Units) to understand what the IRS may ask for during the audit, and being cognizant of the various privileges (e.g., attorney-client, tax practitioner and work product) and recent positions taken by the IRS with respect to whether certain advice provided by accountants is privileged.

Facebook Battles IRS In Summons Enforcement Case

by Jean A. Pawlow and Kevin Spencer | Aug 12, 2016 | Court Procedure Matters, IRS Audits, Privilege and Non-Disclosure, Transfer Pricing Resource, Trial Courts, Uncategorized

Facebook is in a protracted battle with the IRS related to its off-shoring of IP to an Irish affiliate. Read more here. The IRS issued an administrative summons for the documents, and Facebook has refused to comply with the summons. The IRS is asking the court to enforce the summons and force Facebook to turn over the requested documents. The court agreed that on its face, the summons was issued for a legitimate purpose. Facebook will now have to tell the court why it refuses to turn over the documents. Review the court order here. Assumedly, Facebook is asserting that it is not required to disclose the requested materials based upon a claim of privilege. The case demonstrates that the IRS is aggressively seeking documents and information from taxpayers and their representatives in cases involving international tax issues.

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