First ChatGPT Plus Weekly Recommendations for Blogging (10/23/26)

I thought that I would provide in regular blog entries the ChatGPT Plus weekly recommendations that I discuss in Starting Regular Use of AI to Assist in Writing Federal Tax Procedure Blog Entries (Federal Tax Procedure Blog 10/20/26), here. (I use ChatGPT Plus, but will regularly shorthand that the ChatGPT.) Today was the first installment. I will regularly provide links to the ChatGPT responses which for this week’s installment are here, but perhaps for a few weeks will copy and paste the responses. I note in red my action, if any, with the recommendations. 

Federal Tax Procedure Case Watch

October 23, 2026 | Review period: October 16–23, 2026

My leading recommendation is a follow-up on United States v. Sagoo. A new Fifth Circuit order bears directly on your earlier discussion of FBAR penalties, the Seventh Amendment, and SEC v. Jarkesy. I also found an interesting administrative-law issue in a new Tax Court opinion you have already discussed, plus two developments worth considering outside the strict new-opinion category.

1. Highest priority: United States v. Sagoo — FBAR penalties and jury-trial rights

No. 25-11271 (5th Cir. Oct. 22, 2026) — order vacating and remanding.

The Fifth Circuit has ordered further consideration of a district court decision holding that the IRS violated a taxpayer's Seventh Amendment rights by administratively assessing approximately $1 million in FBAR penalties without a prior jury trial.

The remand follows the Supreme Court's June 4, 2026 decision in FCC v. AT&T, Inc., 608 U.S. ___ (2026). That decision distinguished SEC v. Jarkesy, 603 U.S. 109 (2024), and upheld an administrative penalty procedure under which the government must obtain a judicial determination in a de novo proceeding before compelling payment.

The Fifth Circuit's October 22 action is a remand order, not a precedential merits opinion resolving the FBAR issue. I have verified the reported disposition but have not independently obtained the order's full text.

Why this is particularly appropriate for your blog

You discussed the district court decision in your September 24, 2025 entry, updated June 7, 2026. Indeed, you anticipated the essential issue. After examining FCC v. AT&T, you concluded that the decision appeared to support the government's position because the FBAR assessment procedure, like the FCC procedure, permits a subsequent de novo judicial determination with a jury.

That makes the Fifth Circuit's action an opportunity to revisit your prediction.

The most interesting question is whether an IRS assessment has legal consequences that distinguish it from the FCC forfeiture order considered by the Supreme Court.

For example, does the government's administrative assessment of an FBAR penalty constitute an adjudication of liability, or is it merely a preliminary step toward a judicial determination? The distinction may depend on the legal consequences of the assessment before a court enters judgment.

Suggested title:

Fifth Circuit Remands FBAR Jury Trial Case in Light of FCC v. AT&T—Did the Supreme Court Already Resolve the Issue? (10/23/26)

Recommendation: High priority. I would consider a short update to your existing entry, with a separate post if the remand presents additional issues worth developing.

Sources: Fifth Circuit appeal docket; Supreme Court opinion in FCC v. AT&T.

JAT Action: I amended the prior blog on Sagoo to note the remand. District Court Holds the FBAR Willful Penalty Requires Opportunity for Pre-Assessment Jury Trial (Federal Tax Procedure Blog 9/24/25; 10/23/26), here.

2. Potential follow-up: Del Monte, LLC v. Commissioner — Golsen and invalid Treasury regulations

T.C. Memo. 2026-107 (Oct. 19, 2026), Judge Urda.

You already discussed this decision in your October 19 entry concerning two syndicated conservation easement cases. I would not recommend another general discussion of their inflated valuations.

However, Del Monte presents a potentially interesting administrative-law issue.

The Tax Court applied the conservation-easement extinguishment-proceeds regulation, Treas. Reg. § 1.170A-14(g)(6), because the Sixth Circuit upheld it in Oakbrook Land Holdings, LLC v. Commissioner, 28 F.4th 700 (6th Cir. 2022).

The Tax Court had previously held the regulation procedurally invalid in Valley Park Ranch, LLC v. Commissioner, 162 T.C. 110 (2024).

Thus, under Golsen v. Commissioner, 54 T.C. 742 (1970), the Tax Court applied a regulation notwithstanding its own contrary conclusion about the regulation's validity.

The interesting question is institutional rather than substantive.

What exactly should the Tax Court do when its own interpretation of federal administrative law conflicts with controlling appellate precedent?

That question is not new, of course. But Loper Bright makes it worth reconsidering.

A useful discussion might distinguish the Tax Court's obligation to follow appellate precedent from its independent obligation to determine the best interpretation of the statute and APA.

A further question is whether the Tax Court's own reasoning about the regulation's invalidity retains any meaningful significance when Golsen requires a contrary result.

Suggested title:

Tax Court Applies a Treasury Regulation It Has Held Invalid—Golsen, Loper Bright, and Judicial Independence (10/23/26)

Recommendation: Moderate priority. Because you have already covered the decision, I would pursue this only if a closer reading of the opinion reveals something genuinely new about Golsen or regulatory validity.

Source: Your October 19 blog entry.

JAT Action: I have added the ChatGPT Plus recommendation at the bottom of my prior blog: Tax Court Decides 2 Bullshit SCE Tax Shelter Cases and, in One, Judge Lauber Calls Out Petitioner's Counsel's Theatrics (Federal Tax Procedure Blog 10/19/26; 10/23/26), here. I did not think it worthy of a separate blog entry.

3. Additional candidate: Tax Analysts v. IRS — AI audit selection and FOIA

No. 25-cv-1409 (D.D.C. Oct. 14, 2026), Judge Christopher R. Cooper.

This opinion predates the October 16 review period by two days, but it is worth flagging because of its close fit with your interests.

Tax Analysts requested records describing the IRS's artificial-intelligence models used to select complex partnerships for examination.

The IRS withheld the records under FOIA Exemption 7(E), which protects certain law-enforcement techniques and procedures.

Judge Cooper agreed that disclosure of the IRS's audit-selection methods could enable taxpayers to evade detection. However, he rejected the IRS's insufficiently supported assertion that the entire records could be withheld.

The court required the IRS to provide a supplemental Vaughn index or declaration explaining why nonexempt portions could not reasonably be segregated. The deadline is November 4, 2026.

Why I think this might interest you

The conventional FOIA issue is straightforward. More interesting is the relationship between increasingly sophisticated IRS audit-selection systems and administrative accountability.

Should the IRS be able to keep its algorithms confidential while disclosing meaningful information about how those algorithms operate?

How can taxpayers evaluate whether algorithmic selection procedures are arbitrary or systematically biased when the underlying criteria are protected from disclosure?

And should the answer differ depending on whether the taxpayer seeks information under FOIA or in discovery in litigation challenging an IRS determination?

The opinion does not resolve these broader questions, but it provides a useful starting point.

Suggested title:

District Court Protects IRS AI Audit-Selection Methods from FOIA Disclosure—But How Much Secrecy Is Justified? (10/23/26)

Recommendation: Moderate to high priority, particularly because of your recent interest in the use of AI in tax procedure.

Read the complete October 14 opinion.

JAT Action: I was aware of the Tax Analysts opinion but I did not it is worthy of a new blog entry at this time. Perhaps after it comes back the district court judge might write something worthy of a blog entry.

4. Significant non-opinion development: IRS acquiescence in Siemens Medical

AOD 2026-2, published October 19, 2026, 2026-43 I.R.B. 510.

The IRS has announced acquiescence in the result only in Siemens Medical Solutions USA, Inc. v. Commissioner, 167 T.C. No. 6 (2026).

The Tax Court held that the extraordinary-disposition regulations under § 245A exceeded Treasury's rulemaking authority.

The IRS accepts the result but does not fully endorse the court's reasoning.

This is not a newly issued judicial opinion. Nevertheless, the Action on Decision is significant enough to warrant attention.

The potential blog issue concerns the meaning of acquiescence in result only.

What is the practical effect when the IRS accepts that a regulation is invalid but continues to disagree with the judicial reasoning supporting that conclusion?

The question is especially interesting after Loper Bright, when the scope of Treasury's statutory rulemaking authority must be independently determined by reviewing courts.

There is also an institutional question: Does acquiescence in result only provide useful guidance to taxpayers and IRS personnel when the disagreement concerns the legal principles governing future regulations?

Suggested title:

IRS Acquiesces in Invalidity of Treasury Regulation but Not the Court's Reasoning—What Does That Mean After Loper Bright? (10/23/26)

Recommendation: Moderate to high priority. This may be more intellectually rewarding than another conservation-easement valuation opinion.

Read AOD 2026-2 in the Internal Revenue Bulletin.

JAT Action: I don’t immediately think this is worthy of a blog entry. I’ll continue to consider it.

Decisions already covered

I also checked your recent blog entries to avoid recommending matters you have already addressed.

Your October 19 post covers Watson Lake Investments, T.C. Memo. 2026-106, and Del Monte, T.C. Memo. 2026-107. Your October 22 post covers Lontrac Enterprises, T.C. Memo. 2026-108.

Your Lontrac discussion is especially interesting because you move beyond the valuation dispute to consider evidentiary equipoise, burdens of proof, adverse inferences, and the meaning of Golsen's requirement that appellate precedent be squarely in point.

I have therefore not treated those cases as subjects requiring new general summaries.

Overall recommendation

For this review period, I found one especially promising new appellate development, Sagoo, and one newly issued Tax Court opinion, Del Monte, that may support a narrower follow-up. I also identified two worthwhile matters outside the strict October 16–23 new-opinion category.

My order of preference for further work is:

1.   United States v. Sagoo — Update your existing FBAR jury-trial discussion.

2.   Siemens Medical — Explore the IRS's acquiescence and its implications for Treasury rulemaking authority.

3.   Tax Analysts v. IRS — Examine AI audit selection, FOIA, and administrative accountability.

4.   Del Monte — Consider a focused discussion of Golsen and conflicting conclusions about regulatory validity.

I would not recommend writing about all four merely because they are recent. The strongest potential posts are those in which the new development permits you to say something about the law that the deciding court or existing commentary has not adequately explored.