Tax Court Warns Counsel in Advance of Trial in Syndicated Conservation Easement Case (10/31/25)

In Cottonpatch Timber Company, LLC v. Commissioner (T.C. No. 26103-22, here, at #54 Order dtd 10/29/25), TN here, Judge Gustafson sent warnings to counsel in a syndicated conservation easement case in advance of the trial setting currently for December 15, 2025. Specifically, he cautioned:

As to valuation, the Tax Court has criticized overvaluation of conservation easements in Mill Road, at *48-53, and in a number of recent opinions in other cases. Petitioner’s counsel should be able, in due course, to explain why its position this case is materially different from the strongly criticized positions in those cases, since a position that ignores those opinions and reflects the gross fallacies in those previous positions might be frivolous, see sec. 6673(a)(2), and trial time spent in disregard of those opinions would likely be a waste.

The Mill Road opinion is here.

In addition, Judge Gustafson closed with this cautionary advice:

          The judge stated to counsel that he is considering the possibility of issuing, at the conclusion of the trial in this case, a bench opinion pursuant to Rule 152. The parties should keep that possibility in mind as they prepare their pretrial memoranda, since in that event there would be no post-trial briefing.

These cautions to counsel echo Judge Buch’s Order with attached extensive bench opinion in a conservation easement shelter. Tax Court Rejects a Bullshit Tax Shelter False Valuation Claim with Warning of Sanctions for Taxpayers, their Counsel, and Expert Witness Proffering the Bullshit (Federal Tax Procedure Blog 7/16/25; 9/10/25), here. I think Tax Court judges are getting less tolerant, rightfully so, considering the massive waste of time for trials to claim grossly inflated valuations for conservation easements.

Tax Court in Reviewed Opinion Holds TEFRA Litigation Time Limits Jurisdictional (10/25/25)

I am late to post on North Wall Holdings, LLC v. Commissioner, 165 T.C. ___, No. 9 (10/21/25) (reviewed opinion, T.C. Case No. 27773-21, here, at # 50 and  GS here). North Wall is the latest on the tax saga starting with Boechler, P.C. v. Commissioner, 596 U.S. 199 (2022), holding that the time limit for instituting CDP Tax Court proceedings is not jurisdictional, meaning that equitable tolling for late filing may apply. In recent Supreme Court jurisprudence, many time limits have been held to be not jurisdictional. The key tax exception is United States v. Brockamp, 519 U.S. 347 (1997), holding that the refund time limits are jurisdictional.

Notwithstanding the general trend, the Tax Court has held § 6213(a)'s time limits for petitions for redeterminations of deficiencies are jurisdictional. Hallmark Research Collective v. Commissioner, 159 T.C. 126 (2022) (unanimous reviewed opinion). Three Courts of Appeals have now held the § 6213(a) time limits are not jurisdictional, thus permitting equitable tolling. See 6th Circuit Joins 2nd and 3rd Circuits in Holding § 6213(a)’s 90--day Petition-Filing Deadline is Not Jurisdictional (8/25/25; 9/8/25), here.

In North Wall, the opinion for the Court finds the TEFRA time limits jurisdictional. The opinion’s detailed discussion of the TEFRA interrelated time frames is quite excellent. I highly recommend. For purposes of this blog entry, the headnotes are sufficient:

          R mailed a Notice of Final Partnership Administrative Adjustment (FPAA) to the tax matters partner (TMP) of PS, a limited liability company treated as a partnership for federal income tax purposes and subject to the TEFRA unified audit and litigation procedures. P, a notice partner, filed a Petition for readjustment of partnership items 168 days after R mailed the FPAA to the TMP. R moved to dismiss P’s Petition for lack of jurisdiction. P objects.

          A TMP may file a petition for readjustment within 90 days of R’s mailing of an FPAA to the TMP. I.R.C. § 6226(a). A partner or group of partners entitled to notice may file a petition within 60 days after the close of the 90- day TMP petition period. I.R.C. § 6226(b)(1); see also I.R.C. § 6231(a)(8) (defining “notice partner”), (11) (defining “5-percent group”).

          The text, context, and relevant historical treatment of the TEFRA petition period establish that the period within which to file a petition is a jurisdictional limit. The text places the petition period within the jurisdictional grant. I.R.C. § 6226(b)(1), (f). In the context of the broader TEFRA provisions, allowing equitable tolling would render [*2] the TEFRA statutory scheme unworkable. Historically, courts have treated the TEFRA petition deadlines as jurisdictional, and Congress has amended TEFRA to specifically account for the effect of the petition deadlines’ being jurisdictional.

          Even setting aside the jurisdictional question, the complex TEFRA statutory scheme indicates that Congress did not intend for the equitable tolling doctrine to apply to untimely TEFRA petitions.

          Held: P’s Petition was untimely.

          Held, further, equitable tolling does not apply to hold open the prescribed periods set forth in I.R.C. § 6226(a) or (b) for filing a TEFRA petition.

Interest in DOJ Tax Reunion/Wake for DOJ Tax Alumni (10/17/25)

I am trying to assess interest among DOJ Tax Alumni for a Reunion/Wake for the Tax Division. Since some DOJ Tax Alumni read this blog, I offer this link to the blog post on the DOJ Tax Alumni Blog I maintain: Fillable On-Line Form to Assess Interest in DOJ Tax Alumni Reunion/Wake (10/7/25), here.

Tax Court Rejects Various Hail Mary Claim, Including APA Claims, to Get Out of Penalty Free (10/8/25)

In Computer Sciences Corp. v. Commissioner, 165 T.C. ___, No. 8 (2025), TC Case No. 4823-21, here, at entry 305 dated 10/6/25*, GS here**, and TN here, the Court (Judge Lauber) issued yet another § 6751(b), here, written supervisor approval opinion where, as in other cases, the taxpayer seeks to avoid an IRS penalty because of a supposed IRS footfault in the penalty assertion process. In addition to the usual § 6751(b) hail mary claims for a get out of penalty free escape, the taxpayer raises Administrative Procedure Act (“APA”) Claims which, I presume, are the reason the opinion was designated for T.C. reporting (as opposed to T.C. Memo or simply an Order).

For persons wanting a preliminary look at the underlying issues of what the case is all about, go to the docket entries linked above at entry 42 Order dated 7/24/23.

I report here on the APA claims, and will then cover its reference to the § 6751(b) regulations adopted in final in December 2024.

I start my discussion with a quote from Bryan Camp’s iconic post The APA Is Not A Hammer (Procedurally Taxing Blog 6/24/22), here, which opens:

Kristin Hickman loves the APA. To channel Jed Rakoff, it’s her Stradivarius, her Colt 45, her Louisville Slugger, her Cuisinart, and her True Love. It’s her Hammer, her righteous Mjölnir.

And when you have a hammer, everything looks like a nail. Including ALL Treasury regulations.

Although Computer Sciences is not directly attacking regulations, the same comment is appropriate here. With the modern claims about the APA, everything begins to look like a nail, so taxpayers unleash the APA to attack IRS action regardless of how far-fetched the attack is.

In Computer Sciences, I introduce the Court’s holdings from the opening relevant headnotes that, while not technically part of the opinion, for present purposes fairly summarize the opinion (after each holding, I provide brief comment for context):

Eighth Circuit Applies First Sec. Bank Limitation to § 482 Intangibles Allocation Despite the Commensurate with Income Standard Enacted in 1986 (10/2/25)

I recently wrote on the 3M case pending in the 8^th Circuit involving the issue of whether the commensurate with income standard in § 482 enacted in 1986 permits the IRS to use § 482 to allocate royalty income to 3M for intangibles it transferred to a Brazilian affiliate in excess of the amount of royalty income permitted by Brazilian law. The full text of the commensurate with income standard  enacted in 1986 is: “In the case of any transfer (or license) of intangible property (within the meaning of section 367(d)(4)), the income with respect to such transfer or license shall be commensurate with the income attributable to the intangible.” See Loper Bright’s Motivated Mistreatment of Statutory Ambiguity and Best Interpretations (Federal Tax Procedure Blog 8/28/25), here.

In 3M Company v. Commissioner, ___ F.4th ___ (8th Cir. 10/1/25), here, the Court held that the IRS could not use § 482's commensurate with income standard to tax a related party affiliate's (3M's)  income on the transfer of intangibles in excess of legal limits permitted by law applying to the party receiving and exploiting the intangibles transferred to it.

I think it might be helpful to illustrate the issue in a simple examples. I start with an example where no legal prohibition is involved: Suppose intangible property in an open market would have commanded a royalty of 10% in an unrelated party transaction (which I will call the fair market value (“FMV”) royalty). But, in a related party transaction, the U.S. party transferring intangibles to the foreign affiliate charged the foreign affiliate a royalty of 5%. The foreign affiliate earns extra income over what it would have earned if it paid the FMV 10% royalty. This example is a classic instance where the commensurate with income standard enacted in 1986 applies to permit the IRS to tax the U.S. affiliate on an additional 5% royalty.

The next example is the same, except the law where the foreign affiliate earns the extra income limits royalty payments to 5%. The foreign affiliate earns extra income by paying 5% rather than the 10% , FMV royalty. The 5% royalty rate is not commensurate with the income. The question in 3M is whether the IRS can apply the FMV commensurate with income royalty rate despite the local law prohibition?

In Commissioner v. First Sec. Bank of Utah, N.A., 405 U.S. 394 (1972), the Court held that pre-amendment § 482 did not permit an allocation where the recipient was not lawfully entitled to receive the income. In 3M, the taxpayer argued and the Eighth Circuit held that the commensurate with income standard did not apply because Brazilian law limited the royalty the 3M affiliate could pay 3M. The IRS argued that the 1986 commensurate with income amendment to § 482 permitted the allocation. I repeat the text of the commensurate with income standard: “ In the case of any transfer (or license) of intangible property (within the meaning of section 367(d)(4)), the income with respect to such transfer or license shall be commensurate with the income attributable to the intangible.” (Emphasis supplied.)

District Court Holds the FBAR Willful Penalty Requires Opportunity for Pre-Assessment Jury Trial (9/24/25; 10/1/25)

I have updated this blog in paragaph 5 below with an analogous case, HDH Group, involving the § 6700 penalty that has similar features to the FBAR willful penalty involved in the main case discussed, Sagoo. I have also updated this blog in paragraph 6 below to provide a link to a good discussion of these cases.

I have written before on SEC v. Jarkesy, 603 U.S. 109 (2024), Preliminary Print here, in§ which the Court held that the Constitution’s Seventh Amendment guaranteeing a jury trial in some cases applied to processes where the Government (SEC there) imposed civil fraud-type penalties (there securities fraud). That is a high-level summary of a fairly complex Supreme Court opinion. Thus, for example, the Tax Court recently held that Jarkesy did not require a right to jury trial before the IRS determined a civil fraud penalty in a partnership equivalent of a notice of deficiency, permitting the partnership to contest in the Tax Court where no jury trial is permitted. Silver Moss Properties, LLC v. Commissioner, 165 T.C. ___, No. 3 (2025) (Reviewed Opinion) (T.C. Dkt. No. 10646-21, here, at Entry # 109, GS here), discussed in Tax Court Rejects SCE’s Hail Mary Jarkesy Pass (Federal Tax Procedure Blog 8/21/25), here.

In United States v. Sagoo (N.D. Tex No. 24-CV-01159-0 Memo Opinion & Order dtd 9/23/25), CL here and GS here, the Court dismissed the Government’s FBAR willful penalty collection suit because the Government assessed the FBAR penalty without affording the penalized party (Sagoo) a pre-assessment jury trial on liability. The opinion is relatively short (8 pages) and rather cryptic in its legal analysis (pp. 4-7). So, I will leave it to readers of this blog to read and consider the legal analysis for whatever it is worth.

JAT Comments:

1. I say that the legal analysis is “rather cryptic.” Of course, as the Sagoo Court develops its legal analysis, the law is straightforward and easily applied to the simple relevant facts. If that were true, then calling the legal analysis rather cryptic is not suggesting a criticism. I question, though, where the legal analysis is as straightforward as the Sagoo presents it. For example, in Silver Moss Properties, LLC, discussing the same issue for the civil fraud penalty where the facts are also cryptic (one page), the Court’s legal discussion (pp. 7-16) covers 9 pages. This suggests that the legal analysis may not be as straightforward as the Sagoo Court presents it, even though Silver Moss Properties, LLC involved the civil fraud rather than the FBAR willful penalty involved in Sagoo.

Tax Court Holds that Partners Unwilling to Settle on Terms Offered Partners Willing to Settle TEFRA Litigation Cannot Intervene if Untimely and No Acceptable Reason for Untimely Intervention (9/19/25)

In Blomquist Holdings, LLC v. Commissioner, 165 T.C. ___, No. 6 (9/1725), TC here at # 364 [Full TC cite and link to come when available], GS here, and TN here, the Tax Matters Partner and some (but not all) wished to participate in one of the IRS settlement initiatives for docketed syndication easement (“SCE”) cases. The particular settlement initiative required all LLC partners to agree to the settlement, meaning that the IRS could assess the settlement tax, penalty, and resulting interest consequences without much further ado. (LLC owners are not technically partners but a treated as partners for most substantive tax purposes and under the TEFRA audit procedures.) For those who are not familiar with the IRS settlement initiatives for SCE cases, an excellent introduction may be found at Hale E. Sheppard, Settling Syndicated Conservation Easement Cases With the IRS, 186 Tax Notes Federal 851 (2/3/26), here. Mr. Sheppard is an excellent tax litigator and is counsel in a number of the SCE cases in the Tax Court, but was not counsel in Blomquist (where the indicated counsel for the petitioner are from the international firm Dentons, here, which has a substantial US presence; those counsel are identified in the Blomquist opinion and may be further identified by searching on the Dentons’ site here).

This opinion in Blomquist rejects an attempt by some but not all partners to avoid the settlement agreement under the procedures in the statute and Tax Court rules for them to do so. In most litigation contexts, this attempt is called a motion to intervene, but the statute and Tax Court rules deal with the partnership version for an unwilling partner specifically. (I use the term unwilling partners; the opinions in the cases use other terms such as nonparticipating partners; the statutory provision is § 6226(c)(2); the Tax Court Rule is 248(b)(4).) The Tax Court (Judge Paris) does an excellent job of going through the rules to show why a timely request to participate in the proceedings is generally required and a late request will be permitted only in circumstances where the tardy request is justifiable. Blomquist holds that the partners trying to avoid the settlement (the unwilling partners) had not shown that the late request was justifiable. (Note that the Blomquist litigation (but not the T.C. opinion) is discussed in Hale Sheppard’s article linked above at pp. 855-856 and p. 857).

Based on Blomquist and other SCE cases where, post-Blomquist, Orders have been entered, I infer the following:

1. Based on recent litigated outcomes, the settlement offer is very good. Which is, of course, why the partners willing to accept the offer appear to have made a good decision, far better than they can hope to achieve in full trial of the matter (which would also require further wasted litigation costs and wasted time from the participants (even with the private attorneys being more than happy to waste time at their exorbitant billing rates), including judges, staff and witnesses). That, however, is just my inference from the cases I have read. In any event, it is clear that there were partners wanting to settle who were motivated, I infer, by the tax outcome (tax and penalties, with interest consequences as well) which is far better than had they litigated.

Do Mixed Questions of Fact and Law Have Component Facts and Law for § 7491(a) Purposes? (9/11/25)

I address today what may seem to be a fairly mundane issue, but in some contexts might be important. Readers may already be familiar with § 7491(a), here, titled “Burden shifts where taxpayer produces credible evidence.” The “burden” referred to is the burden of proof and specifically the burden of persuasion. The burden of persuasion is not technically relevant until the end of trial when it determines which party loses in the event the trier of fact is in factual equipoise as to some key fact. From a practical perspective, it is important to keep in mind the conventional trial wisdom that triers of fact are rarely in equipoise, so that ultimately the assignment of the burden of persuasion is meaningless in most cases. Setting that aside and accepting the possibility that the burden of persuasion may be outcome-determinative in some cases, parties will often want to know before the beginning of trial which party has the burden of persuasion so that it can prove its case accordingly.

That is what happened in FBA St. Clair Property C, LLC v. Commissioner (T.C. Case 14406-23, here, at docket # 176 9/11/25), where the petitioner in a syndicated conservation easement case filed a motion in limine for the Court to hold that the conditions in § 7491(a) assigned the burden of persuasion to the IRS. The Court denied the motion, reasoning (Slip Op. 3-4):

          Section 7491(a) states that if a taxpayer produces credible evidence with respect to one or more factual issues relevant to the taxpayer’s tax liability, the burden of proof may shift to the Commissioner as to that issue or issues, as long as the taxpayer complies with certain additional requirements. Section 7491(a) only applies if the issue is factual and not “a mixed question of fact and law” which is “primarily a legal question.” Williams v. Commissioner, 120 F.App’x 289, 293 (10th Cir. 2005) (denying that § 7491(a) applies to the issue of whether a payment was a gift for purposes of § 102(a) or instead a bonus), aff’g T.C. Memo. 2003-97. Here, the issue is whether the transaction was a contribution or gift for purposes of Section 170(c), and we hold that this issue is a mixed question of fact and law, and so Section 7491(a) does not shift the burden to the Commissioner. 

Loper Bright’s Motivated Mistreatment of Statutory Ambiguity and Best Interpretations (8/28/25)

On August 26, 2025, I gave a talk to a Houston tax group, the Wednesday Tax Forum. The paper I circulated was a high-level summary of a longer article that I have submitted for publication in the ABA Tax Lawyer in Spring 2024; the submitted article addresses the tax implications of Loper Bright Enterprises v. Raimondo, 603 U.S. 369, 377-378 (2024), see Preliminary Print here. I link that summary here so that readers may download if they wish. Note that the linked summary is redlined to show changes that I made shortly after giving the talk. I will not attempt to further summarize the arguments.

I address in this blog entry the overarching claim that I make. The domain of Chevron was a state of ambiguity where the court was not able to determine whether the agency interpretation or an opposing interpretation was the best interpretation. I call that state interpretive equipoise to relate it to the more familiar concept of factual equipoise where a factfinder is unable to determine whether a critical fact exists or not. In a state of factual equipoise, the factfinder resolves the issue by holding against the party bearing the burden of persuasion on that fact. In a state of interpretive equipoise, the court cannot find that either the agency interpretation or the opposing interpretation is the best interpretation. Chevron resolved the case in that state of interpretive equipoise, effectively placing on the opponent of the agency interpretation a burden to persuade the court that its opposing interpretation was “best.”

Why did Chevron tilt in favor of the agency interpretation in a state of interpretive equipoise? First consider the alternatives. Would it be acceptable for courts to decide in equipoise by flipping a coin, consulting a ouija board or soothsayer, or some other unprincipled way of resolving the ambiguity? Of course, that would not be acceptable. Still, courts must resolve interpretive issues in equipoise in some way. Chevron offered that way. I will address below why that is a principled resolution based on the APA, but I ask first what Loper Bright offered in lieu of Chevron to resolve cases of interpretive equipoise?

Loper Bright offers nothing for interpretive equipoise other than the ill-considered notion that courts can always interpret out all ambiguity to derive the single best interpretation. That would be nice if it made logical sense or experiential sense. Courts have the same interpretive skills after Loper Bright that they had under Chevron where they were admonished by Chevron’s famous footnote 9 to use those skills to avoid ambiguity where possible. Nevertheless, in some cases, ambiguity remained. I submit that cases of ambiguity—interpretive equipoise—will remain under Loper Bright. Loper Bright offers no guidance on what a court does where, using its best interpretive skills in de novo review, ambiguity exists.

Traditional Skidmore will not solve the problem of interpretive equipoise. Traditional Skidmore simply requires courts to respect agency interpretations in determining the best interpretations. The phenomenon I address here is where, after using all of those tools of interpretation (including Skidmore), the court cannot determine, as between the agency interpretation and the opposing interpretation, which is the best interpretation. Both interpretations must be in play—that is reasonable within the scope of the statutory ambiguity—but neither is the best interpretation. In that state of play, Loper Bright offers no way to resolve the case.

Of course, I say traditional Skidmore. Skidmore has traditionally been called Skidmore deference even though it was not deference but simply a consideration in reaching the best interpretation. See Really, Skidmore "Deference?" (Federal Tax Procedure Blog 5/31/20; 2/14/21), here. It is possible that, post-Loper Bright, courts may reimagine Skidmore to fill some of the conceptual space on the spectrum between respect and deference, sort of more than respect but less than deference, if that is a possible thing, say deference “light.” I can’t offer anything meaningful on that possibility.

6th Circuit Joins 2nd and 3rd Circuits in Holding § 6213(a)’s 90--day Petition-Filing Deadline is Not Jurisdictional (8/25/25; 9/8/25)

In Oquendo v. Commissioner, ___ F.4th ___ (6th Cir. 8/25/25) (CA6 here, TN here, and GS here), the panel held unanimously that § 6213(a)’s 90-day petition-filing deadline was not jurisdictional and is thus subject to equitable tolling; so finding the panel remanded to the Tax Court to consider Oquendo’s entitlement to equitable tolling. The holding is consistent with prior decisions by the Second Circuit and the Third Circuit. Buller v. Commissioner, ___ F.4th ___ (2d Cir. 8/13/25); and Culp v. Commissioner,  75 F.4th 196 (3rd Cir. 2023), cert. den. ___ U.S. ___, ___ S.Ct. ___, 2024 U.S. LEXIS 2725 (2024). See Second Circuit Allows Possible Equitable Tolling for 90-day Petition for Redetermination of Deficiency (Federal Tax Procedure Blog 8/14/25), here (discussing Buller and Culp). The Supreme Court denied the Commissioner’s petition for cert in Culp; as I said in the blog on Buller, I doubt that the Government would file a petition for cert with two losses and no wins in the Courts of Appeals; now there is three losses and no wins.

JAT Comments: 

1. I suspect that the issue will not go to the Supreme Court before an actual conflict develops in the Courts of Appeals and then, of course, it would be the taxpayer petitioning for cert.

2. More likely, now with three losses, I suspect that the Tax Court will reconsider its position that § 6213(a)’s 90-day petition-filing deadline is jurisdictional. There should be cases in the pipeline that will permit the Tax Court to do that expeditiously if it wants to act expeditiously.

3. Moreover, I suspect that the Tax Court may relax its sparing approach to finding a taxpayer can satisfy the requirements for equitable tolling; if the Tax Court does not, the Courts of Appeals may intervene as these cases are appealed. On the Tax Court’s sparing approach to finding equitable tolling, see the blog cited above, quoting from the Federal Tax Procedure Book Editions.

4. (Added 9/8/25 @ 2:15pm): I note to readers an excellent article on the Buller and Oquendo appellate decisions. Robert S. Horwitz, With Strikes in the Third and Now the Second and Sixth Circuits, Will the Commissioner Admit He Is Out on the Claim that the 90-Day Deadline for Filing a Tax Court Petition Is Jurisdictional? (Tax Litigator 9/8/25), here. (Note that there are references to §6713(a) that should be to §6713(a), but readers can quickly adjust to that and read the excellent article.)