Lesson From The Tax Court: Form Trumps Substance On Phantom S Corp Income

This past June, the Supreme Court issued an opinion in Moore v. United States, 144 S.Ct. 1680 (June 20, 2024).  There, the taxpayers were shareholders of an American-controlled foreign corporation called KisanKraft and were being taxed on a portion of the corporation’s income that had been earned long ago and far away but never actually passed on to them substantively.  The unhappy taxpayers protested that Congress could not constitutionally tax them on income they had not realized through actual receipt.  To them it was phantom income.  Form could not, constitutionally, trump substance.

In explaining why the taxpayers were wrong, Justice Kavanaugh reviewed how Congress has historically chosen to make the owners of certain business entities responsible for paying tax on the entity’s income, regardless of what the entity actually does with that income.  He also reviewed how courts have routinely upheld that Congressional choice.

Today’s lesson is an example of that routine application of Congressional choice.  It also carries a cautionary lesson for taxpayers: choose your business partners carefully!  You do not want to go into business with Gru and Dru.  In James J. Maggard and Szu-Yi Chang v. Commissioner, T.C. Memo. 2024-77 (Aug. 7, 2021) (Judge Holmes), Mr. Maggard was a 40% shareholder of an S Corporation controlled by two other shareholders who, over the course of several years “made unauthorized distributions to themselves in excess of their proportionate ownership shares.” Op. at 1.  Judge Holmes translates this into plain English: they looted the corporation.  While the looting gave the taxpayer an argument to avoid taxation, it was not a winning argument.

Sad details below the fold.

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Lesson From The Tax Court: The Shrinking §469 Exception For Active Participation

Section 469 generally denies taxpayers the ability to use net losses from passive activities to offset income from active activities.  Renting real property is a passive activity.  But there are some exceptions when it comes to renting real estate.  Two are relevant for today’s lesson.  First, taxpayers who are real estate professionals can deduct such losses.  Second, individual taxpayers who actively participate in a rental activity can use up to $25k of net losses to offset other income ... if they are not too rich!

Today we learn how difficult it can be for taxpayers employed in a full-time job to claim they are a real estate professional.  We also learn how second exception is shrinking.  In Timothy L. Foradis and Jessica L. Moore v. Commissioner, T.C. Summ. Op. 2024-13 (July 11, 2024) (Judge Leyden), the married taxpayers attempted to deduct some $22k in net rental losses on their 2020 return.  But they were too rich!  That exception closes when taxpayers have AGI of over $150,000.  This couple had total wage income of just over $161k.  So they were forced to try and sell Mr. Foradis as a real estate professional.  It did not go well.

Details below the fold.

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Lesson From The Tax Court: Finding Safe Harbors From The §72(t) Early Distribution Penalty

Congress wants taxpayers to save for retirement.  To encourage such savings, Congress authorizes a smorgasbord of tax-advantaged retirement plans that taxpayers can use.  Authority for such plans are scattered in different statutes, such as §401, §403, and §408.  Again, the purpose of these provisions is to allow taxpayers to save for retirement.  Congress give other ways for taxpayers to defer taxation on savings for other purposes, such as post-secondary education.  See e.g. §529.

To reinforce the focus on using these accounts for retirement and not for other purposes, Congress imposes a 10% penalty—er—I mean “addition to tax” when taxpayers take distributions from qualified retirement plans too soon before retirement.  §72(t).  Yeah, §72(t) is titled “10-percent additional tax on early distributions from qualified retirement plans.”  But as I explain in the Coda at end of this post, its operative language is indistinguishable from §72(q) which is titled as a “10-percent penalty....”  So let’s just call it what it is:  a penalty for early distributions.

How soon is too soon?  Age 59½.  §72(t)(2)(A).  Any distribution made before age 59½ is deemed to be an early distribution and subject to the 10% penalty.  I have no idea who came up with 59½ as the magic line.  I welcome comments from knowledgeable readers on whether it had anything to do with budget scoring.  I think of this as the general rule, applicable to all types of retirement accounts: early distributions pay the penalty.

Over the years Congress has created rules allowing early distributions to be made without penalty, but only if they are taken for certain purposes.  I think of these rules as exceptions—safe harbors—to the general rule of 59½.

These safe harbors can be complex and we learn today that you need to be very careful when trying to navigate into one of them.  In Edward George Shilkas v. Commissioner, T.C. Summ. Op. 2024-10 (June 20, 2024) (Judge Panuthos), the taxpayer took an early distribution that may have escaped penalty if taken from the right type of account.  But the taxpayer took it from the wrong type of account.  In Caren Kohl v. Commissioner, T.C. Summ. Op. 2024-4 (Apr. 25, 2024) (Judge Siegel), the taxpayer took a distribution that may have escaped penalty if taken in the right year.  She took it in 2018 for a purpose that Congress later decided should not be subject to the 10% penalty, but the later-created safe harbor was not available in 2018. 

Details below the fold. 

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Lesson From The Tax Court: Proving Last Known Address

Many statutes require the IRS to send taxpayers notices.  What confuses my students (and many taxpayers) is that the statutes rarely require that the taxpayer actually receive a particular notice; they just require the IRS to properly send the notice.  And the IRS will always meet the statutory requirement if the IRS sends the notice in question to the taxpayer’s “last known address.”  As you can guess from the scare quotes, that phrase is a term of art.

Today we learn a lesson about that term of art.  It’s a lesson that has a wide application because the IRS sends out lots of notices and people move all the time.  Where they lived last year is not always where they live this year.  If they have multiple addresses, it may not be clear which one counts as their “last known address.”  If the IRS goofs up sending a notice, that generally means the notice is invalid ... if the Court is convinced about the goof.

Normally, it’s up to the taxpayer to persuade a court that the IRS goofed up.  The law presumes that the IRS does not goof up.  That presumption means the courts will find a notice was properly sent unless the taxpayer convinces the court otherwise.  That means even if the court has doubts about what was the proper last known address, the IRS still wins if the taxpayer cannot meet their burden of persuasion.

Sometimes, however, the burden shifts to the IRS.  That is the lesson we learn in Keith M. Philips v. Commissioner, T.C. Memo. 2024-44 (Apr. 16, 2024) (Judge Greaves).  There the IRS sent Mr. Phillips an Notice of Deficiency (NOD) but Mr. Phillips was able to shift the burden of persuasion so that doubts about whether the IRS properly sent the NOD to his last known address were resolved in his favor, not the IRS’s.  Thus, the NOD was invalid because the IRS could not convince the Judge Greaves that it sent the NOD to his last known address.  This well written opinion was a pleasure to read.  We can learn a good lesson here.

Details below the fold.

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Lesson From The Tax Court: When Is An Excise Tax Really A Penalty?

“The power to tax involves the power to destroy.” Justice John Marshall in McCulloch v. Maryland, 17 U.S. 316, 431 (1819).

“Sometimes a tax is...just a tax.” — Sigmund Freud’s Tax Advisor.

Today’s lesson is about how to tell when an excise tax is really a penalty.  The answer I learn is: “why do you want to know?”  I hope to explain why that answer makes the most sense.

In Clair R. Couturier Jr. v. Commissioner, T.C. Memo. 2024-6 (Jan. 17, 2024) (Judge Lauber), the IRS sent the taxpayer a Notice of Deficiency for over $8 million.  The basis for the proposed deficiency was that Mr. Couturier had made an excess contribution of over $25 million to his IRA, thus triggering the excise tax imposed by §4973 on excess IRA contributions.

In Tax Court, Mr. Courturier—well represented by Taylor, Nelson and Amitrano—argued that the §4973 “tax” was really a “penalty.”  If true, that meant that the IRS needed to have followed the supervisory approval procedures for penalties in §6751(b), which it had not.  The IRS argued that it did not have to follow the §6751(b) supervisory approval procedures before sending out the NOD because the tax was ... just a tax!

Judge Lauber’s opinion explains why the §4973 excise tax was not a penalty for purposes of the §6751(b) supervisory approval requirements.  Keith Fogg has a really good post on this issue here, where he suggests a potential tension between what he describes as the Tax Court’s textual analysis (focusing on the labels) and what he describes as the Supreme Court’s functional analysis about a similar excise tax in U.S. v. Reorganized CF & I Fabricators of Utah, Inc., 518 U.S. 213 (1996), a bankruptcy case.

I see the matter a bit differently than Keith.  Different statutes (e.g., bankruptcy statutes, statutes imposing interest) treat penalties differently than they treat taxes.  The lesson I learn is that looking to see whether an excise tax operates in some abstract sense as a penalty is not the strongest analysis.  Instead, the better analysis is to see whether treating it as a penalty is more appropriate under the relevant statutory scheme than treating it as a tax.  In other words, why do you want to know?

Details, and a fuller explanation, await those intrepid readers who continue below the fold.

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Lesson From The Tax Court: The Interplay Of SSDI Benefits And The §104(a)(1) Exclusion

When Congress giveth a tax benefit with one hand, it sometimes taketh the other hand and slaps the taxpayer silly, eliminating the benefit the taxpayer thought they had.  Today's lesson is an example of that phenomenon.  It’s kind of like a bad joke, an appropriate lesson for April 1st.

Specifically, the one hand is found in §104(a)(1).  It promises taxpayers they can exclude from gross income those “amounts received under workmen’s compensation acts as compensation for personal injuries or sickness.”

The other hand comes in §86(d).  In Donald Ecret and Kristen Ecret v. Commissioner, T.C. Memo. 2024-23 (Feb. 14) (Judge Lauber), the taxpayers got slapped by that statute with the result that most or all of otherwise excludable workers compensation payments became taxable income.  In today's case Ms. Ecret received workers compensation from the state of New York after becoming medically disabled.  When she became entitled to Social Security Disability payments, she actually received only a fraction of the benefits she was entitled to receive because of a federal statute that requires the Social Security Administration (SSA) to offset the entitlements by sate workers compensation received.  Judge Lauber give a very well-written lesson on why the taxpayer must report even the unpaid federal benefits as gross income: it’s because of §86(d).  So, yes, technically the state benefits were still excluded under §104(a)(1).  But the practical effect of the SSA offset was to reduce the exclusion by forcing the taxpayer to include in income those unpaid SSDI benefits, withheld from the taxpayer because of the offset.  In effect, §86(d) transmogrifies the excludable state benefits into taxable Social Security benefits. Thanks Congress!

Details below the fold.

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Lesson From The Tax Court: Taxpayer Excused From Providing Sewage-Soaked Receipts

Section 162 permits taxpayers to deduct all the “ordinary and necessary expenses” they incur in carrying on their trade or business.  Generally, we know that taxpayers who claim §162 deductions must substantiate them.  Generally, we know that means taxpayer must provide receipts. Cohan v. Commissioner, 39 F.2d 540 (2d Cir. 1930) Of course, taxpayers must do more than just substantiate an expense; they must be sure to tie that expenses to their business, as we learned in Lesson From The Tax Court: Receipts Are Not Enough, TaxProf Blog (Sept. 21, 2020). 

Today we learn of an interesting exception to the receipt requirement.  In H. DeForest Boegart v. Commissioner, T.C. Summ. Op. 2024-4 (Mar. 4, 2024) (Judge Panuthos), the taxpayer took the stand and, through his dramatic testimony, explained how a clogged sewer line had backed up into his basement and soaked all of his paper receipts with ... well ... sewage.  While he offered to provide the soggy mess to the Court, Judge Panuthos permitted the taxpayer to substantiate the expenses solely through oral testimony, writing “we don’t need no stinking receipts."

The messy details are below the fold.

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Lesson From The Tax Court: Choose Your Return Preparer Carefully

In Stephanie Murrin v. Commissioner, T.C. Memo. 2024-10 (Jan. 26, 2024), Judge Urda decided that the fraudulent acts of a return preparer starting in 1993, made an honest taxpayer liable for some $65,000 in deficiencies resulting from the 30-year old fraud of someone else, plus some $15k in §6662 penalties.  That is, the return preparer’s fraud opened up the unlimited period in §6501(c)(1) for the IRS to assess the deficiency against the taxpayer.  In doing so Judge Urda adhered to the Tax Court’s precedential opinion of Allen v. Commissioner, 128 T.C. 37 (2007).  It is no small irony to me that Allen was written by Judge Kroupa, who was later convicted of tax evasion.

Let me emphasize that there was no hint in the facts of today's case that the taxpayer knew or should have known of the return preparer’s fraud.  That is, the government made no attempt to impute the return preparer’s fraud to the taxpayer.  The government made no attempt to prove the taxpayer had any fraudulent intent to evade her tax obligations.  Yet here we are, over 30 years later with the government seeking to collect tax and penalties when the normal statute of limitations is three years.

Pull up your jaw.  Unless and until the Tax Court’s recent re-interpretation of the §6501(c) fraud exception to the general three year SOL for assessment gets changed, taxpayers and their representatives must deal with the results.

Sad details below the fold.

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Lesson From The Tax Court: For Whom The SOL Tolls

A recent Tax Court precedential decision raises a really interesting question about the application of §7451’s tolling provision to seemingly late-filed Tax Court Petitions.  In Madiodio Sall v. Commissioner, 161 T.C. 13 (Nov. 30, 2023) (Judge Buch), the deadline for the taxpayer to file his Petition fell on Thanksgiving Day.  We all know that means that the deadline got kicked to the next day, Friday.  Thanks §7503!  But the taxpayer did not file on Friday.  Nope.  The taxpayer did not even put his Petition in the mail until the following Monday.  For reasons I’ll get into below, Judge Buch ruled that §7451’s tolling provision applied to extend the filing deadline for two weeks after Friday. 

So for this taxpayer, the Statute of Limitations (SOL) for filing a timely Tax Court Petition was tolled.  But this taxpayer was attempting to file by hard-copy.  Another recent Tax Court precedential  opinion—also by Judge Buch—suggests that the question of for whom the SOL tolls may have a different answer if the taxpayer attempts to file electronically, as all taxpayers may choose to do so, and as many are required now to do.

Details below the fold.

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A Year Of Lessons From The Tax Court (2023)

Here is a chronological listing of all the Lessons From The Tax Court I posted in 2023, with links to the Lesson, the primary case discussed, and its author.  I have also listed the primary Code sections mentioned or discussed in the Lesson.  At the end of the chronological listing, you will find a table listing the posts by which Tax Court Judge authored the Court's opinion.

January 23: The Meaning Of 'Business Premises' In §119, Cory H. Smith v. Commissioner, T.C. Memo. 2023-12 (Jan. 12, 2023) (Judge Toro) — §119

January 30: Corporations In The Bardo, XC Foundation v. Commissioner, T.C. Memo. 2023-2 (Jan. 5, 2023) (Judge Lauber) — §7428, Rule 60(a), California Revenue and Taxation Code (RTC) §23301 - §23311, §4941, §7428, §4941

February 6: The Tax Court Is Not Your Advocate, Robert B. Lucas v. Commissioner, T.C. Memo. 2023-9 (Jan. 17, 2023) (Judge Urda) — §72(t), §213

February 13: Mortgage Interest Deductions When The Payor Is Not The Borrower, Hrach Shilgevorkyan v. Commissioner, T. C. Memo. 2023-12 (Jan. 23, 2023) (Judge Ashford) — §163, §280A(d)(1), Treas. Reg. 1.121-2(b)(2)

 

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Lesson From The Tax Court: Taxpayers Behaving Badly 2023

[Author's note: This will be my last new post until January. Next Monday, December 18, my annual Year Of Lessons From The Tax Court will appear in this space. It is a chronological listing of all the Lessons I posted in 2023, with links to each Lesson, the primary case discussed, and the judge who wrote the opinion. You can find last year's edition here.

I will be spending my days (except for Christmas Day) grading exams.  Grades are due Monday, January 2nd and then I resume teaching on January 8th, so you will see my next post on Monday January 22nd, when I will have some news to share.] 

Once again my last new post of the year presents cases where something in the facts made me just shake my head (SMH in texting parlance).  You can find the previous lists here (for 2018), here (for 2019), here (for 2020), here (for 2021) and here (for 2022).

This year I have six to share with you.  I present them in chronological order.  I invite you to consider which of theme may be examples of just an empty head and which are examples of something worse.  In addition, I once again have found a worthy recipient for the Norm Peterson award. 

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Lesson From The Tax Court Repost: Ipse Dixit Cannot Fix It

[Author's Note: I am preparing exams and so take a break this week from writing a new Lesson.  I offer a reposting of a Lesson from 2019 that I really liked, but one that did not get a lot of views when originally posted.  I hope you enjoy it!]

Mitchel Skolnick and Leslie Skolnick, et al. v. Commissioner, T.C. Memo. 2019-64 (June 3, 2019) (Judge Lauber), teaches an important lesson about the proper use of expert witnesses.  In Skolnick, the Tax Court rejected the taxpayer’s expert witness valuation of of 153 horses at two points in time 7 years apart because the expert did not adequately disclose the facts and methodology used to value each horse.  Judge Lauber held that the taxpayer could not fix the value of the horses through expert’s ipse dixit.

The form of the lesson is also instructive.  The opinion merely grants an interstitial motion, called a motion in limine, to exclude the expert’s report from the evidentiary record at trial, held in April 2019.  The 68-page final decision was issued in December 2019 (you can read it here) and the taxpayers lost, as you might expect. They then took an appeal to the Third Circuit...and lost again. Skolnick v. Commissioner, 62 F.4th 95 (3rd Cir. 2023).

One might ask why the Court would take the time to issue an opinion on just one aspect of a case after the bother of a trial.  Why did not the Court just issue an opinion on the merits of the dispute?  After all, if the expert’s opinion is worthless enough to exclude from evidence, it is unlikely to really be helpful in deciding the merits of the case. 

I give my thoughts on both lessons below the fold, although I won’t blame you if you prefer to just watch this classic Monty Python sketch “The Argument Clinic.” Ipse Dixit is the form of argument that predominates in the sketch and is part of what makes it funny.  In real life, however, taxpayer representatives who do not heed today’s lesson will not be laughing.

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Lesson From The Tax Court: Taxpayers Cannot Invoke The 'Augusta Rule' With Unplayable Lie

In the past few years there have apparently been a lot of excited Tik Tok posts about how closely held businesses can use the “Augusta Rule” to get a double tax benefit: a deduction for the business under §162 and tax free income to the business owner under §280A(g).

In Kunjlata J. Jadhav and Jalandar Y. Jadhav v. Commissioner, T.C. Memo. 2023-140 (Nov. 21, 2023) (Judge Vasquez), the taxpayers get lured by the promise of tax free income under the August Rule into making what turned out to be an unplayable lie on their tax returns.  They did not get a mulligan.  They did get penalties.  The problem was these taxpayers were unable to show that the rental payments their S Corp made to them and their sons were “ordinary and necessary” under §162.  That requirement is not usually a difficult one to meet but when you are trying to play the system, it can be tricky to get through the rough and avoid the hazards to make the hole.

Details below the fold.

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Lesson From The Tax Court: A Lesson In Pathfinding

I cannot say it enough: the IRS is not an entity.  It’s a vast organization with various offices that perform various functions.  And one key idea is that taxpayers may have multiple paths to get to a successful result.  If one office cannot help you perhaps a different one can.  At the IRS that often means if you cannot get good results in Exam or Collection you might get them in Appeals.  And sometimes you can get to Tax Court from Appeals.  But sometimes not.  It's path dependent as we learn today.

In Rita Renee Pilate v. Commissioner, T.C. Memo. 2023-136 (Nov. 9, 2023) (Judge Gustafson), the IRS was seeking to collect a tax liability.  The taxpayer was able to obtain a CDP hearing.  That path put her in front of the Office of Appeals.  She said she wanted to make an Offer In Compromise (OIC).  But she did not submit one to Appeals as part of the CDP hearing.  She did not choose that path.  After Appeals closed her CDP hearing, Ms. Pilate timely petitioned the Tax Court for review.  She also now submitted an OIC but, since her CDP case had closed, that submission put her on a different path.  The OIC was accepted but a dispute later arose on whether she complied with its terms and Appeals issued a letter defaulting her.  Since her CDP petition was still before the Tax Court, she asked the Court to review the Appeals decision to default her OIC.  The Tax Court said it could not make that review, because an OIC outside of CDP is not on the correct path for judicial review.

Details below the fold.

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Lesson From The Tax Court: Merely Winning Does Not Entitle Taxpayer To Attorneys Fees

Section 7430(a) permits a court to award “reasonable administrative costs” and “reasonable litigation costs” (the largest being attorneys fees) to a taxpayer who is a “prevailing party” in a dispute with the IRS.  I use all those scare quotes to emphasize that these are all terms of art.  And the scariest, or artiest, one is perhaps “prevailing party.”

Today’s lesson teaches us that a taxpayer is not going to be a prevailing party just because they win a remand in the Court of Appeals and then win in Tax Court on the remand.  The case is Champions Retreat Golf Founders, LLC v. Commissioner, T.C. Memo. 2023-143 (Nov. 8, 2023) (Judge Pugh).  It is the coda on the taxpayer’s 13 year slog to claim a $10.8 million charitable deduction for a conservation easement on a golf course.  The Tax Court initially found that the easement was not a qualified charitable contribution.  It got reversed by the Eleventh Circuit.

The parties then battled over the proper valuation of the donation and, again, the taxpayer won, although Judge Pugh cut down the contribution amount by about $3 million. See Lesson From The Tax Court: Fake It Till You Make It, TaxProf Blog (Oct. 24, 2022) (“The lesson is kind of like the old joke that you don’t have to outrun the bear: a taxpayer’s valuation does not have to be the best possible; it just has to be better than the IRS’ valuation.”).

Now the taxpayer is back, asking for the Court to make the government pay its litigation costs per §7430 because it claims to be a prevailing party.  Well, without the scare quotes, that may seem intuitively right.  After all, the taxpayer won in the Circuit Court and then in Tax Court on remand!

But the lesson we learn is that even a winning taxpayer is not entitled to litigation costs when the government’s losing position was “substantially justified.”  Again with the scare quotes!  That’s because, dear readers, this term is yet another term of art.  We learn today that the term is a facts and circumstances determination.  While winning is an important factor, winning isn’t everything.  Details below the fold. 

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Lesson From The Tax Court: §6662 Is Sometimes Multiple Penalties For Supervisory Approval Purposes But Sometimes Not

This week we learn a lesson about the interplay between the supervisory approval requirement in §6751(b) and the §6662 penalty regime.  While §6662(a) seems to impose a single penalty for accuracy-related error, we learn that if the IRS is either careful or lucky, it can cure one defective §6662 approval by later asserting in Tax Court a seemingly different §6662 penalty and getting the proper supervisory approval for that second bite at the penalty apple.

In Stephen R. Kelley and Isabelle Kelley v. Commissioner, T.C. Memo. 2023-126 (Oct. 23, 2023) (Judge Copeland), the NOD asserted a §6662(a) penalty for substantial understatement.  But the IRS employee had not obtained the appropriate supervisory approval before the NOD went out.  So when the case got to Tax Court, the IRS conceded the substantial understatement penalty and the IRS Chief Counsel attorney asserted a §6662(a) penalty for negligence or disregard of rules or regulations.  The taxpayers argued that the penalty imposed by §6662(a) is singular and so the failure to obtain supervisory approval for the NOD precluded any later assertion of penalties under §6662(a).

The Tax Court rejected the taxpayer’s argument and held that the §6662(a) penalty for substantial understatement was different than the §6662(a) penalty for negligence or disregard.

This decision seems in tension with a prior precedential Tax Court opinion, Jesus R. Oropeza v. Commissioner, 155 T.C. 132 (2020), where the Tax Court seemingly held that it would treat §6662 as imposing a single penalty for §6751(b) purposes.  I blogged that in Lesson From The Tax Court: §6662 Penalties Treated As One For Supervisory Approval Requirement, TaxProf Blog (Oct. 19, 2020).

Judge Copeland does not mention Oropeza in her otherwise very comprehensive 19 page opinion, much less seek to distinguish it.  I think the cases are reconcilable but it makes for an awkward lesson: sometimes §6662 imposes a singular penalty and sometimes it imposes multiple penalties for supervisory approval purposes.  This awkwardness seems unavoidable under any interpretation of §6751(b).  It comes from the ambiguity of §6662 and not the nonsensical text of §6751(b).

Details, as always, below the fold.

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Lesson From The Tax Court: The Rules For Penalty Approval Depend On Geography

Tax law is supposed to be uniform.  The thousands of pages of statutes and regulations are supposed to be applied to taxpayers living in Texas in the same way as taxpayers living in California.  The IRS is a single federal agency charged with applying the law uniformly.  And the Tax Court is a single national trial court that can and does travel to every corner of the United States to resolve most disputes that arise between taxpayers and the IRS.

But tax law is not uniform.  One reason is because there are 11 geographic Circuit Courts of Appeals (Circuits 1-11 plus the D.C. Circuit) in the federal system.  Their decisions are binding within the geographic boundaries of the Circuit, but are not binding on the other Circuits.  So when one Circuit Court of Appeals disagrees with another on how to interpret a tax statute, the law is not uniform.  Under what is known as the “Golsen rule” the Tax Court will generally follow the law of the Circuit to which a taxpayer would take an appeal.

Today we learn another reason tax law is not uniform: the Tax Court itself.  In Wolfgang Frederick Kraske v. Commissioner, 161 T.C. No. 7 (Oct. 26, 2023) (Judge Gale), the taxpayer was arguing that the IRS could not assert penalties because the penalties were not properly approved under §6751(b).  That argument was a winner under the Tax Court’s interpretation of that statute, but was a loser under the interpretation given by every one of the four Circuit Courts of Appeals to interpret the statute, including the Circuit to which the taxpayer would take an appeal.  This might have been a good case for the Tax Court to change its interpretation and bring uniformity to tax administration.  Sadly, that did not happen.  Instead Judge Gale applied the Golsen rule, which teaches us another good lesson: the Golsen rule is not automatic!

Details, as usual, below the fold.

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Lesson From The Tax Court: What Makes A NOD Invalid?

When the IRS determines a deficiency of tax, it is then “authorized to send notice of such deficiency to the taxpayer.”  §6212(a).  That’s called a Notice of Deficiency (NOD).  The taxpayer generally has 90 days from the date of the NOD to petition the Tax Court to ask for a “redetermination of the deficiency.” §6213(a).

The procedures outlined in §§6212 and 6213 carry several important consequences.  First, the IRS is prohibited from sending a second NOD for the tax year(s) covered by the NOD. §6212(c)(1).  Second, the IRS is prohibited from assessing the proposed deficiency until after the Tax Court has issued a decision and it has become final. §6213(a).  Third, the statute of limitations for the IRS to make an assessment is suspended for the same period during which the IRS is prohibited from assessing, plus 60 days. §6503(a).

None of those consequences happen if the NOD is invalid.  If a taxpayer convinces the Court that the NOD is not valid, the Tax Court will dismiss the case.  That dismissal hurts the IRS because, almost always, the limitation period for assessment will have expired, barring the IRS from re-doing the NOD.

So what makes an NOD invalid?  It is not what many taxpayers think.  Taxpayers may think that an indecipherable NOD is invalid.  Or taxpayers might think that if the process leading to the NOD was defective, then the NOD is invalid.  Today we learn that is not the case.  The lesson comes from Michael J. Watson and Tracy L. Watson, et al. v. Commissioner, Docket No. 12220-21 plus five others (Aug. 31, 2023) (Judge Weiler). Note that this is an unpublished order, so the link takes you to the Docket Sheet and you have to scroll down to find the Order.

But even though this is just an unpublished order, I think it’s worth attention because it is very well written and can teach us something about how the Tax Court evaluates the validity of an NOD.

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Lesson From The Tax Court: The Limits Of Collection Due Process

One lesson I teach my students is that taxpayers are generally best off resolving issues with the IRS before seeking judicial help. Another lesson is that taxpayers have multiple opportunities to work with the IRS in the collection process.  So just because one opportunity fails does not mean the taxpayer is out of options.

Today we see a great example of both lessons in Eric Wilfred Olson v. Commissioner, T.C. Memo. 2023-123 (Oct.10, 2023) (Judge Weiler).  There, the taxpayer attempted to use the Collection Due Process (CDP) opportunity to stave off enforced collection of some $77,000 of tax liabilities.  He was also trying to get spousal relief for his wife.  The Tax Court gave him no relief because he had failed to properly try and resolve these issues at the administrative level.  However, just because CDP relief was not available did not mean the taxpayer was out of options to obtain the relief he appears to have sought.

The case also shows the limits of CDP’s delay benefit.  While delay is certainly a common benefit of the CDP process, that benefit was limited in this case for two reasons.  First, this was a tax lien CDP case, which mean the IRS had already established the priority of the tax lien by filing a Notice of Federal Tax Lien (NFTL) before the CDP process started. §6320(a).  So the CDP process in such cases does not affect the IRS ability to use its lien powers.  Second, the taxpayer here filed his Tax Court petition in October 2022 and Judge Weiler issued his decision less than one year later.  That’s awesomely fast for a CDP case.  See Lesson From The Tax Court: The Long And Short Of CDP, TaxProf Blog (Apr. 6, 2020).  No wonder Lew (“Don’t Contact Me”) Taishoff gives Judge Weiler the cognomen “Speedy”!

Details below the fold. 

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Lesson From The Tax Court: The Designated Payment Rule

Payroll taxes present particularly prickly problems.  The problems often arise from a failure to make timely deposits of the correct amounts.  That can happen for lots of reasons, some innocent, some willful.  But once the employer gets too messed up, fixing the problem can be tricky because the IRS will take whatever payments are made and apply those payments in the best interest of the government.  That may not always be in the best interest of the taxpayer.

Today we learn a lesson that will help taxpayers mitigate payroll tax goofs: a voluntary payment allows taxpayers to designate how the IRS should apply the payment.  It's a useful lesson for any kind of tax but especially for payroll taxes.  In Raymond S. Edwards v. Commissioner, T.C. Summ. Op. 2023-29 (Sept. 27, 2023) (Judge Panuthos), the taxpayer got crosswise with the IRS on unpaid payroll taxes and sent in payments that he specifically designated to cover only the taxes owed for five specified quarters, not the accrued interest and penalties, which he wanted to contest.  But the IRS instead applied the payments to interest and penalties.  Judge Panuthos explains why the IRS must honor a taxpayer’s designation of voluntarily remitted taxes.  Not sure this was more than a pyrrhic victory, but it makes for a good lesson.

Details below the fold.

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Lesson From The Tax Court: Equitable Tolling During Government Shutdown?

Like winter, a shutdown is coming.  And last week, the Tax Court issued a really important reviewed decision about equitable tolling of CDP hearings.  The two are connected because the Tax Court lesson may become very useful for taxpayers faced with an inaccessible IRS during periods of government shutdown

For those of us having a hard time keeping track, this Wikipedia entry gives a useful history of federal government shutdowns.  Going in reverse chronological order, it appears that top three were: (1) during the Trump administration—one at the start of 2018 and then also a long 35-day shutdown from the end of 2018 into 2019; (2) during the Obama administration—16 days in 2013; and (3) during the Clinton administration—21 days in in 1995–1996.  We may well be on the way to another one when the 45-day Continuing Resolution passed yesterday expires.

Last week's opinion in Organic Cannabis Foundation v. Commissioner, 161 T.C. No. 4 (Judge Goeke), may help taxpayers who must deal with a closed IRS during the next shutdown.  In that case, fourteen of the sitting Tax Court judges interpreted §6320 to permit equitable tolling of the 30-day period that taxpayers have to request a CDP hearing after the IRS files a Notice of Federal Tax Lien (NFTL).  Three judges thought that interpretation squarely conflicted with the applicable Treasury Regulation and wanted to hear arguments on the validity of the regulation.  The Court’s reasoning applies as much to §6330 CDP hearings as well, making it even more consequential.

What makes this a really useful decision is the idea that a government shutdown might indeed qualify taxpayers for equitable tolling.  Details below the fold.

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Lesson From The Tax Court: Supervisory Approval Of Automated Penalties

Section 6751 requires the IRS to ensure adequate supervisory approval of tax penalties before those penalties are assessed.  But it does not require such approval for any “penalty automatically calculated through electronic means.” §6751(b)(2)(B).

Today we learn a surprisingly nuanced lesson about what constitutes a penalty automatically calculated through electronic means.  In Piper Trucking & Leasing v. Commissioner, 161 T.C. No. 3 (Sept. 14, 2023) (Judge Foley), the IRS assessed penalties against the taxpayer, under §6721, for Piper’s alleged failure to file required information returns.  The initial letter proposing such penalties was automatically generated, based on information received from the Social Security Administration.  But the proposed penalties were the most severe of several alternatives, alternatives that depended on the facts.  Yet no IRS employee was supposed to review the penalty unless and until the taxpayer responded to the initial letter in time.  In this case, the taxpayer made no timely response.  For that reason, the Tax Court held that these penalties fell within the statutory exception and required no human decisionmaker.

This lesson is just another reason why taxpayers need to be sure to respond to all correspondence received from the IRS.  Details below the fold.

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Lesson From The Tax Court: When 'My CPA Did It' Is No Defense To Penalties

Life is complex.  Tax shadows life.  So it is no wonder that Tax law is complex.  And the more complex a taxpayer’s financial life becomes, the more likely they will goof up.  While Congress imposes penalties for errors, it also recognizes the complexity of tax law by allowing taxpayers to avoid most penalties if they can show they had reasonable cause for their errors.  A common defense against penalties is that the taxpayer reasonably relied on the advice of a competent professional.

Sometimes, however, taxpayers think that relying on a professional to prepare the return absolves them of responsibility for any subsequent errors.  Today’s lesson puts the lie to that thought.  Relying on a CPA’s return preparation services is not the same as relying on a CPA’s advice and provides no protection from the various penalties in §6662.

In John R. Johnson, et al. v. Commissioner, T.C. Memo. 2023-116 (Sept. 13, 2023) (Judge Nega), the taxpayer was hit with §6662(b) penalties for substantially understating his income tax liabilities for four years in a row.  That’s a lot of error.  He argued that he had reasonable cause for the errors because he had used a CPA to prepare his returns and he had provided that CPA all the relevant information.  He even put his CPA on the stand.

The failure of that argument provides the lesson.  We learn that to avoid penalties taxpayer must do more than show they relied on a CPA to properly prepare the return, especially when the taxpayer is sophisticated.  Details below the fold. 

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Lesson From The Tax Court: The Boundary Waters Of Equity

Every birthday gives me the opportunity to appreciate the luck I've had in my life.  Last week was my 63rd.  I fondly remembered my summers at  Camp Chippewa, a wonderful summer camp just outside of Bemidji, MN.  One focus of that camp was canoe trips, including trips exploring the Boundary Waters in upper MN and lower Canada.  Those 1-2 week trips were amazing adventures.  Long before cell phones and GPS, we were cut off from any easy access to population centers.  Only if you were careful with your maps would you even know whether you were in the U.S. or in Canada!  And yes, I will connect that up with Today’s Lesson.

These particular reminiscences were sparked by my reading William H. Evenhouse and Nelle L. Evenhouse v. Commissioner, T.C. Memo. 2023-113 (Sept. 7, 2023) (Judge Lauber), because we learn there how the Tax Court interprets §6213 generously to allow certain lucky taxpayers up to 150 days to petition for review of a Notice of Deficiency (NOD).  While the particular taxpayers in this case were not able to get the extra time, the case gives us a good lesson in how the Tax Court decides when a taxpayer gets the 150-day period rather than the usual 90-day period to petition for review of an NOD.  In my mind, it’s a lesson in equity.  That could be very useful if and when taxpayers are able to start arguing for equitable tolling of the usual 90 day period.

Details below the fold.

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Lesson From The Tax Court: Cannot Use CDP To Contest Trust Fund Recovery Penalty

Unpaid employment taxes are a substantial problem for both the government and taxpayers. From the government’s perspective this Treasury website tells us that “employment tax violations represented more than $91 billion of the gross Tax Gap and, after collection efforts, $79 billion of the net Tax Gap in this country.”

From the taxpayer’s perspective, dealing with payroll taxes is a real pain.  It’s all too easy to get the tax accounting and quarterly reporting misaligned with the IRS, and resolving those disputes takes time and energy.  Especially when the IRS believes taxes are not being paid, the IRS may start to look at assessing a personal liability against the owners and operators of the business under §6672, the Trust Fund Recovery Penalty (TFRP).

Today we learn that once the IRS assesses a TFRP liability against a taxpayer, that taxpayer will not be able to contest their liability during a later Collection Due Process (CDP) hearing.  In Mark P. Hafner v. Commissioner, T.C. Sum. Op. 2023-27 (Aug. 29, 2023) (Judge Weiler), the taxpayer got hit with a proposed TFRP penalty and contested it in the Office of Appeals.  He lost and the TFRP was assessed against him.  In a later CDP hearing the taxpayer again tried to contest his liability, but both the Office of Appeals and the Tax Court refused to even hear his arguments.  He was not able to use CDP to get pre-payment judicial review of his liability.  Details below the fold.

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Lesson From The Tax Court: Tax Protesting—A Hobby That Eats

Everyone should have a hobby.  Generally, hobbies are good for you, as this Utah State University Mental Health Education post explains.  But some hobbies become cancerous, becoming all-consuming.  Those hobbies are not good for you.  As Benjamin Franklin reportedly put it: beware the hobby that eats.

Protesting your taxes is a hobby that eats.  Bob Wood once wrote this great blog post about stupid tax protest arguments. The legal term for “stupid” is, of course, “frivolous.” Bob rightly says it’s one of the worst names you can be called in the tax world.  I really love his line: “In IRS lingo, it’s about as bad as you can get, just shy of the other “f” word, fraudulent.”

That is why I call tax protestors “hobbyists.”  They simply advance stupid reasons for not paying taxes, to the point where their hobby consumes them and others, at great cost.  That’s the lesson we learn in  Lawrence James Saccato v. Commissioner, T.C. Memo. 2023-96 (July 25, 2023) (Judge Lauber), where the taxpayer failed to file returns for some 14 years.  When caught, he persisted in protesting that he was exempt from income tax because, among other stupid reasons, he was “ a citizen of the State of Oregon” and not a “federal citizen.”  The Court’s reaction was to impose a §6673 penalty on top of a deficiency topping $200k.  His hobby was eating him up.

The sad details are below the fold.  

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Lesson From The Tax Court: Tax Consequence For Discharge Of Non-Recourse Debt

One of the hard concepts to teach students is the different tax treatments for recourse loans and non-recourse loans.  It gets especially confusing when the sale of underwater property includes a Discharge of Indebtedness (DOI) as part of the sale.  In Michael G. Parker and Julie A. Parker v. Commissioner, T.C. Memo. 2023-104 (Aug. 10, 2023) (Judge Nega), we learn that discharge of non-recourse debt as a result of a property sale cannot generate DOI income (and thus cannot qualify for exclusion under §108) but must instead be used in calculating gain from the sale.

In today’s case the taxpayer’s S Corporation sold some underwater property and the deal included a discharge of part of the unpaid debt.  They argued that they were insolvent at the time of the deal and thus attempted to exclude the DOI from income under the insolvency exclusion allowed by §108(a)(1)(B).  But because the cancelled debt was non-recourse, the taxpayers could not use §108.  Instead, the amount discharged had to be included in the calculation of gain and thus §108 could not apply.  It’s a basic, yet complex, lesson.  Details below the fold.

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Lesson From The Tax Court: Gotta Get Physical For Casualty Loss Deduction

Individuals generally cannot deduct casualty losses, at least through the end of 2025.  §165(h)(5). But Congress continues to permit individual taxpayers to deduct casualty losses if they are attributable to a federally declared disaster. Id. 

And we are having more and more disasters.  Call it climate change, call it a banana, the brutal fact is that “the number of natural disasters per year has increased significantly in recent years.” That quote is from this June 2023 Forbes Advisor article, which goes in to great detail explaining that conclusion.  And there has been a corresponding increase in FEMA disaster declarations over time as well.  See Congressional Research Services “Stafford Act Declarations 1953-2016: Trends, Analyses, and Implications for Congress,” (Aug. 28, 2017). 

So today’s lesson is still useful even if Congress never restores the general casualty loss deduction.  In Thomas K. Richey and Maureen P. Cleary v. Commissioner, T.C. Memo. 2023-43 (Mar. 28, 2023) (Judge Holmes), we learn the basic, but vital, lesson that that a taxpayer must prove that some identifiable event caused actual physical damage to their property.  Just because there is a storm and you then spend money on your property does not prove the storm caused damage to your property.  In today’s case the taxpayers reported casualty losses of some $820,000 for damages to their vacation home and boat.  But they were unable to prove the claimed losses arose from a casualty event.  Details below the fold.

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Lesson From The Tax Court: An Object Lesson On Adequate Business Records

[Author’s Note: this past week I joined the 77.5% of Americans who been infected with COVID.  So tired .... zzzzz ** what?  So this week’s lesson may reflect my COVID-fogged brain.  If you find more errors than usual, I humbly apologize and promise to do better next week.]

Some of my Lessons From Tax Court address substantive tax rules.  Some are about practice and procedure.  Today we have an object lesson: when a taxpayer has a bona fide business but fails to keep adequate records of their business activity, bad things happen.

We all know that taxpayer’s need good records to substantiate claimed deductions. See e.g. Lesson From The Tax Court: Receipts Are Not Enough, TaxProf Blog (Sept. 21, 2020).

This week we also learn that: (1) the failure to keep records allows the IRS to use the bank deposits method to determine income and (2) the same failure also gives the IRS a slam-dunk basis to impose §6662(a) accuracy-related penalties.

The case is Greg A. Ninke and Jane M. Ninke v. Commissioner, T.C. Memo. 2023-88 (July 19, 2023) (Judge Halpern).  Again, nothing really new here.  But it's a useful object lesson. Details below the fold.

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Lesson From The Tax Court: Size Does Not Matter

In Janet R. Braen et al. v. Commissioner, T.C. Memo. 2023-85 (July 11, 2023) (Judge Urda), we learn that there is no charitable deduction for a bargain sale done to settle a lawsuit, even though it was a huge bargain sale.  There, the taxpayers claimed a $5.2 million charitable contribution deduction from a bargain sale they had made with a New York town called Ramapo.  Judge Urda needs every one of 39 pages to explain the complex facts and apply them.  But the basic Lesson I see in the case is this: even a big bargain sale to a charity requires donative intent.  Without a donative intent, there is no §170 deduction, no matter how big the bargain.  Intent is determined by objective facts surrounding the transaction.  Here, those facts showed that the taxpayers’ intent was not to be charitable; their intent was to settle a lawsuit they had filed against the town.  By settling they avoided the risk of a more adverse outcome had the lawsuit proceeded, and they regained their right to develop the land they did not sell.  I confess this is not quite the way Judge Urda sees the case.  So see what you think.  Details below the fold. 

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Lesson From The Tax Court: Creating Your Best Administrative Record

When the Tax Court reviews an IRS Collection Due Process (CDP) decision about collection, it always uses an abuse of discretion standard of review.  That is, it does not simply substitute its judgment for that of the Office of Appeals Settlement Officer (SO), but instead looks to see whether the SO committed an error of law or made a decision that was whacko.

However, in conducting its abuse-of-discretion review, the Tax Court does not always use the same information set.  It depends on where the taxpayer would take an appeal.  If the taxpayer would take an appeal to the 1st, 8th, or 9th Circuits, the Tax Court will base its review solely on the administrative record provided by the IRS.  No new information will be allowed.  However, for appeals to any other Circuit, the Tax Court will also consider any additional information the parties bring up at trial.

Today’s case involves the administrative record review and teaches us what the practitioner can do during the CDP hearing to maximize chances in Tax Court if a petition becomes necessary.  In Duane Whittaker and Candace Whittaker v. Commissioner, T.C. Memo. 2023-59 (May 15, 2023) (Judge Holmes), the taxpayers used their 2019 CDP hearing to submit an OIC.  They not only provided detailed information but they also offered to provide additional substantiation if asked.  Then COVID happened.  In 2020 the taxpayers sent in additional information to show how their financial situation had deteriorated.  Again, they offered to substantiate their claims if asked.  They were not asked.  That turned out to be key because it resulted in information gaps which, if filled, might have led the SO to a different conclusion.

It was these gaps in the administrative record that caused the Tax Court to find an abuse of discretion and remand the case back to Appeals to fill in the gaps.  The Tax Court faulted the IRS for the gaps because the IRS had not asked for more information.  Details below the fold.

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Lesson From The Tax Court: Freedom, Taxes, And Hobbies

We have great freedoms in this country.  Freedom to express ourselves.  Freedom to fish.  Freedom to write blog posts.  Freedom to pursue any lawful activity to make money.  Truly ours is a great civilization well worth tomorrow's celebration.

But.

To riff on a well worn aphorism: with great freedom comes great responsibility.  In particular, as the Sainted Justice Holmes told us: “Taxes are what we pay for civilized society.... The constitutional right...to earn one's livelihood by any lawful calling certainly is consistent, as we all know, with the calling being taxed.” Compania General de Tabacos v. Collectorv, 275 U.S. 87, 100 (1927).

Three recent cases on Hobby Loss rules teach us about the responsibility of paying taxes to support our freedoms: you cannot lower your taxes by deducting the costs of your personal hobby.  The basic lesson is the importance of record-keeping.  That means more than keeping proper records.  It means properly using the records in a business-like manner.  In contrast, having “meticulous” records may just rescue a taxpayer who erroneously mashes up their hobby with a legitimate business activity on the same Schedule.

Two of the three cases present garden variety fact patterns where taxpayers attempt to disguise personal expenditures as business expenses.  In Donald E. Swanson v. Commissioner, T.C. Memo. 2023-81 (June 29, 2023) (Judge Pugh), the taxpayer was an emergency room doctor and amateur musician who created a vanity website for his music.  In Joseph William Sherman v. Commissionerv, T.C. Memo. 2023-63 (May 17, 2023) (Judge Jones), the retired taxpayer was an avid fisherman who also sometimes hired himself out as a guide, generating some hobby income to reduce his hobby expenses.

The third case is twisty.  In Leslyn Jo Carson & Craig Carson v. Commissioner, Dkt. No. 23086-21S (May 18, 2023) (Judge Morrison), the taxpayers mashed up a hobby activity (kids doing rodeos) with a business activity (ranching).  What triggered the audit was that the ranch was owned by the taxpayer’ wife's mom and they had an agreement that all ranching income would be allocated to Mom and all ranching expenses would be paid for and deducted by the taxpayers.  So the taxpayers essentially reported massive ranching expenses against modest hobby income.  However, these taxpayers' great recordkeeping overcame their poor reporting, winning a no-harm-no-foul ruling from the Tax Court. 

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Lesson From The Tax Court: How To Calculate Insolvency For The §108 Exclusion

While not as certain as death and taxes, small businesses failures are highly probable events.  This webpage from the Bureau of Labor Statistics goes into the gnarly. 

When a small business fails, that often means it cannot repay loans.  A lender will often write off the loan as a bad debt, discharging the borrower from the obligation to repay.  That discharge is taxable income to the borrower, unless they qualify for an exclusion.  Today’s lesson involves the insolvency exclusion in §108(a).  To qualify for that, one has to be (duh) insolvent!  Insolvency is tested at the time of the discharge.  Section 108(d)(3) defines insolvency as "the excess of liabilities over the fair market value of assets."  But nothing in the statutes or regulations defines the term "liabilities."

Katrina E. White v. Commissioner, T.C. Memo. 2023-77 (June 21, 2023) (Judge Paris), teaches a lesson about what types of obligations count as liabilities in determining insolvency for §108(a) purposes.  We learn that a liability which is legally enforceable, and due and owing at the time of the discharge, counts even if the lender takes no action to actually collect or enforce the debt.  Details below the fold.

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Lesson From The Tax Court: The Administrative Record Rule In Whistleblower Cases

Law is a slow-moving conversation.  I tell my students that one law year is seven human years, kinda like one human year is seven dog years.  So it was only a couple of years ago, in 2006, that Congress created the current whistleblower award program in the Tax Reform and Health Care Act of 2006, 120 Stat. 2922, 2959.  The provisions are codified in §7623.  Since then, the Tax Court has been in a slow-moving conversation with the D.C. Circuit and Treasury to develop the law.

Today we see how the Tax Court engages with Treasury regulations to apply something called the administrative record rule to the specifics of the IRS whistleblower program.  In Jeremy Berenblatt v. Commissioner, 160 T.C. No. 14, (May 24, 2023) (Judge Copeland), the unhappy whistleblower wanted the Tax Court to force the IRS to disclose information that the IRS said was outside the administrative record.  Judge Copeland’s excellent and nuanced opinion explains what constitutes the administrative record and the limited circumstances where a litigant can make the IRS add to the administrative record.  It’s complicated.  But we can find at least two lessons worth noting.  First, the IRS enjoys a very strong presumption that what it provides as the administrative record is complete.  Second, the Treasury regulations defining what constitutes the administrative record also enjoy a strong presumption of completeness.  Even a litigant as well represented as Mr. Berenblatt could not overcome those presumptions.  That is because a litigant must show more than some set of documents were available to the IRS; they must show that the documents or materials were considered, either directly or indirectly by the IRS office making the decision.  Details below the fold.

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Lesson From The Tax Court: The IRS's Substantial Justification Defense To §7430 Fee Awards

Getting an award under §7430 is hard, even if the taxpayer totally wins.  The major stumbling block is a statutory escape hatch called substantial justification.  If the IRS’ shows that its position was substantially justified at the relevant time, the taxpayer is not entitled to fees and costs even if the taxpayer wins on the merits.  But the relevant time may be different depending on whether the taxpayer is seeking recovery of administrative costs or litigation costs.  In Josefa Castillo v. Commissioner, 160 T.C. No. 15 (June 5, 2023) (Judge Kerrigan), we learn that the IRS must be able to show substantial justification at two different points in the process.  There, the Court found the IRS was substantially justified at the litigation stage.  But the IRS may not have been substantially justified at the administrative stage.  That may be why the IRS conceded a §7430 award as to administrative costs, even while successfully resisting an award of litigation costs.  The ultimate result reflects well on the taxpayer’s representative, Professor Elizabeth A. Maresca and her team at the Fordham Low Income Taxpayer Clinic.

This case involves the time period in §6330(d)(1) for taxpayers to seek Tax Court review of an adverse Collection Due Process (CDP) decision.  For decades the IRS and Tax Court believed that 30-day period was a jurisdictional requirement.  The Tax Court simply did not have the power to hear a late-filed petition.  The Supreme Court, however, held otherwise in Boechler v. Commissioner, 596 U.S. ___ (2022).  Today’s lesson concerns the consequences of the Boechler decision on the recovery of costs and attorneys fees under §7430.  It’s a surprisingly nuanced lesson.

Alert readers should note that this is a potentially important lesson for deficiency petitions.  That is because the IRS and Tax Court have a similar long-standing belief that the 90-day period in §6213 for NOD petitions is jurisdictional.  And that position, too, may be soon be rejected, at least by the Third Circuit.  The case to watch for is Culp v. Commissioner.  In this recent oral argument before the Third Circuit, the taxpayer was fortunate to have the terrific advocacy skills of Oliver Roberts and Professor Keith Fogg.  While one never knows until the opinion issues, one gets a sense that the Circuit Court panel was quite sympathetic to the argument that §6213 is not jurisdictional.  The panel even went to the extraordinary length of asking Professor Fogg to give additional oral argument!  For more on the Culp case, see Carl Smith’s post here over at Procedurally Taxing.  But for the lesson on how substantial justification works, the details are below the fold.

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Lesson From The Tax Court: Substantiating Gambling Losses On Per-Casino Basis

The old saying “you win some, you lose some” is not true for most recreational gamblers.  For them, the saying is more like “you win some, you lose more.”  But proving that proves a problem.  In Jacob Bright v. Commissioner, Docket No. 10095-22 (May 4, 2023), Judge Buch teaches us how taxpayers can use their player cards to substantiate their wagering losses.  There, Mr. Bright reported some $241,000 of wagering gains on his 2019 return, and an equal amount of losses.  However, he apparently did not follow best practices—as very nicely explained in this article—of keeping daily contemporaneous records.  When audited, the IRS accepted his self-reported income (natch!) but disallowed all the losses for lack of substantiation (double natch!).

In Tax Court, Judge Buch allowed Mr. Bright to introduce reports of his player card activity, from each of the three Casinos he gambled at in 2019.  That created a sufficient basis for the Court to use the Cohan rule, albeit differently for each Casino.  The Court used this method to estimate $191,000 of losses.  In taking this approach for calculating wagering losses, Judge Buch gives us a new idea of “per session” netting worth considering, not only for proving up wagering losses, but also for calculating wagering gains.  I would call it a “per establishment” approach.  It makes a good bit of sense.  Details below the fold.

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Lesson From The Tax Court: On Time Is Late

In law, even more than in comedy, timing can be critical.  In comedy you just lose a laugh.  In law, you lose a case.  In Roy A. Nutt and Bonnie W. Nutt v. Commissioner, 160 T.C. No. 10 (May 2, 2023) (Judge Buch), we learn why a petition seemingly submitted on time will be rejected as late.  There, the Nutts electronically submitted their Petition to the Tax Court on the last day they could file.  Now we all know you really don't want to ever do that.  But sometimes it just happens.  And the last day to file is just as timely as the first day to file.  The Nutts submitted their Petition at 11:05 p.m.  So they seemed to be on time.

The problem was that they were filing from Alabama (Central Time) and the Tax Court’s Clerk’s office is in Washington D.C. (Eastern Time).  Thus, even though they submitted on time, Judge Buch holds that their Petition was filed late, because 11:05 p.m. in Alabama was five minutes after midnight in Washington D.C.  Thus, sticking to its increasingly archaic view that the timing rules for filing a Petition are jurisdictional, the Tax Court dismissed the Petition.

Note this is another precedential opinion issued in a case with unrepresented taxpayers.  Here, the IRS moved to dismiss and briefed the issue, but there was no responding brief to counter the government’s view.  These pro-se taxpayers probably did not know about all the Tax Court precedent applying equitable principles to rescue seemingly late-filed petitions.  I give a close review of those cases in Bryan Camp, Equitable Doctrines and Jurisdictional Time Periods, Part 2, 159 Tax Notes 1581 (June 11, 2018).

To his great credit, Judge Buch has, in a similar case, asked for amicus briefs on the issue.  I hope the Tax Court there comes to a different conclusion.  It’s always a balancing act: weighing the need for taxpayer access to judicial review with the need to obey statutory limits. Perhaps the Tax Court might reconsider how that balance should work for electronically filed documents.  However, as Professor Book puts it in this post over at Procedurally Taxing, after this case taxpayers now have a steeper hill to climb. You will find the sad details below the fold, along with my modest thoughts on how to strike a better balance. 

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Lesson From The Tax Court: Allocating Between Excludable Child Support and Includable Interest

As inflation rises so does interest in interest.  Certainly when my 1-year CD matures next month I will be looking for a rate better than the 2% rate that seemed so great last year!  If I get a 4.5% I will be happy ... but who knows what my dollars will be worth next year?

And that’s how we typically think of interest: it’s all about inflation, the old idea that “dollars tomorrow will be worth less than dollars today.”  But the concept of “interest” is a bit more nuanced than just being compensation for the diminished value of dollars in the future.  It is also a compensation for risk: the risk that the money will not in fact be repaid—think junk bonds.  And interest also compensates for opportunity costs: a lender is giving up the ability to use (consume or invest) that money now.  In short, interest is compensation for multiple consequences of the use or forbearance of money, similar to how rent is compensation for several different sticks of property rights given up by the lessor.

It is for these reasons that interest has always been taxed as a separate item of income, separate and apart from the underlying loan or deferred payment.  We see that lesson again today in Susan D. Rodgers v. Commissioner, T.C. Memo. 2023-56 (May 9, 2023) (Judge Gale), where the taxpayer received periodic payments from the State of Alabama in 2015 that it had collected from her ex-spouse to satisfy a court judgment for child support arrearages, plus interest.  She treated all the payments as excludable child support despite receiving a 1099-INT from Alabama that treated all the payments as interest on the arrearages.

Thus this case also presents a lesson in allocation.  How should a taxpayer decide how much of a given payment represents taxable interest or non-taxable child support?  And on that issue, dear readers, I think the Tax Court may have been misled by the State of Alabama into ignoring federal law to find that all of each payment was interest.  Details below the fold.

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Lesson From The Tax Court: Exclusion Rules For Disability Payments

A tax break is just another way of saying “government subsidy.”  Most folks do not even think about that when they get a medical bill.  They are generally just upset about the size of the co-pay!  But Congress subsidizes medical care by allowing taxpayers to exclude from income everything the health insurance plans pay the medical providers above the co-pay.

The scope of that subsidy, however, depends on who pays for the insurance in the first place.  If the taxpayer pays for the insurance, the exclusion is governed by §104(a)(3).  That provision does not just exclude payments for actual medical services.  It excludes any and all amounts paid on account of physical injury or sickness.  In contrast, if the taxpayer’s employer pays for the insurance, then the exclusion is governed by §105(b) and that is a more restrictive exclusion.  The §105 exclusion is limited to actual reimbursements (or payments) for identified medical care.

The differences between the §104(a)(3) exclusion and the §105(b) exclusion are most apparent when a taxpayer receives disability payments, as we learn in Cynthia L. Hailstone and John Linford v. Commissioner, T.C. Summ. Op. 2023-17 (Apr. 24, 2023) (Judge Leyden).  There, the taxpayer received disability payments and attempted to exclude those from income.  That might have worked under §104(a)(3) if the taxpayers had paid for the insurance, but since the payments at issue came from an employer-paid plan, the exclusion was not permitted, per §105(b).  Details below the fold.

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Lesson From The Tax Court: Better Deals With Appeals

One recurring lesson I teach in Tax Practice and Procedure is that you generally serve your client better by resolving their issues at the lowest level.  That requires helping them be realistic in understanding the range of potential outcomes.  It requires an understanding that IRS offices, such as the Office of Appeals, generally have more discretion than does the Tax Court to resolve problems.  It also requires understanding that when the Tax Court reviews an IRS discretionary action, it will only change that action when it is convinced the IRS decision was bonkers or, in the dry technical terms of the law, the decision was an “abuse of discretion.”  And, no, the Tax Court will not make a taxpayer’s argument for them, as we recently learned in Lesson From The Tax Court: The Tax Court Is Not Your Advocate, TaxProf Blog (Feb. 6, 2023).

Today I present a case where pro se taxpayers learned that lesson the hard way.  In Ronald Powell and Cynthia Powell, T.C. Memo. 2023-48 (Apr. 17, 2023) (Judge Lauber), the taxpayers did not like the Installment Agreement offered them by Appeals.  They thought they could do better in Tax Court.  They thought wrong.  Details below the fold.

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Lesson From The Tax Court: Prepare Once, File Twice

Most of us don’t think about what it means to file our tax return.  We may rely on software or a hired return preparer to transmit our return to the IRS. The returns are either snail-mailed to the applicable Service Center, or they are e-filed to that amorphous “cloud.”  We know it is important to file our returns in order to trigger the 3-year limitation period for assessment in §6501(a).  But once we send them in, we’re done.

But most of us do not claim to live in the U.S. Virgin Islands (USVI).  Taxpayers who do may need to file twice, as we learn in David W. Tice v. Commissioner, 160 T.C. No. 8 (Apr. 10, 2023) (Judge Pugh). a reviewed Tax Court opinion.  In holding that the taxpayer was obligated to file his returns with both the USVI and the IRS, the opinion reverses the Court’s prior approach, which we learned about in Lesson From The Tax Court: Forms Follow Function In Return Filing, TaxProf Blog (Jan. 5, 2018).  Previously, the Court had focused on the passive voice of §6501(a) to decide that filing only once with USVI triggered the three year limitation period when the USVI sent a couple of pages of the return to the IRS.  Today’s opinion reads the active voice of §932(a)(2) as imposing a more robust obligation.  Intervening Treasury Regulations might comfort those who believe they only need file once.  However, more cautious advisors may still want to prepare once and file twice.  See what you think.  Details below the fold.

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Lesson From The Tax Court: The Actual Payment Doctrine

Today is a lesson in timing.  When I teach timing I emphasize to my students that they must analyze income items separately from deduction items.  Today is an example of how the analysis applicable to inclusion can be different from the analysis applicable to deductions.

As to income, we all know about the constructive receipt doctrine.  Even if a taxpayer has not actually received some slug of money, they are deemed to have constructively received it if the money was made available to them in the year and there was no legal restriction on their accessing it.

Today’s lesson teaches that the deduction analysis is different.  To take a deduction the taxpayer must make an actual payment.  There is no such thing as constructive payment.  In Edwin L. Gage and Elain R. Gage v. Commissioner, T.C. Memo. 2023-47 (Apr. 12, 2023) (Judge Holmes), the taxpayers purchased a cashier’s check in December 2012 to settle a lawsuit and gave it to their attorney.  They took a 162 deduction for 2012, even though their attorney did not deliver the cashier's check to to the opposing party until March 2013.  In holding that they could not deduct that payment in 2012, Judge Holmes explains why their commitment to pay and their actual purchase of a cashier’s check did not amount to making an actual payment in 2012.  Details below the fold.

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Lesson From The Tax Court: It Takes More Than Putting In The Hours To Avoid §469 Restrictions

Tax Day approaches.  I know many folks are putting in the hours on preparing tax returns this week ... or else putting in the minutes filing Form 4868.  But we all know—especially when unhappy clients come to us to fix a return messed up by some whack-a-doodle preparer—just putting in hours in filing tax returns does not make one a tax professional.

In Robert L. Drocella and Pamela M. Drocella v. Commissioner, T.C. Summ. Op. 2023-12 (Apr. 3, 2023), Judge Leyden teaches us, and our clients, that simply putting in the hours working on one’s rentals does not make one a real estate professional for §469 purposes.  There the hard-working taxpayers were not allowed to escape §469’s prohibition on taking passive activity losses against active income even though they together put in over 1,500 hours in working their six rental properties.  We learn today there are two other tests to being a real estate professional and these taxpayers failed one of them:  they were unable to show the Court the how the hours they worked their rentals related to the hours they spent earning wages.  Details below the fold.

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Lesson From The Tax Court: Attend Carefully To Your Entity Baskets

Easter approaches.  On that day our church grounds will be overrun with children scampering to collect eggs into the various baskets, bags, and other containers they bring (or we give them if they need).  They do not have to worry about what kind of container they use to collect their eggs.  The candy will taste just as sweet.

You can think of business entities as being like Easter baskets.  They are containers taxpayers use to collect their income.  But unlike the happy children, taxpayers must take care in their choice of container.  That choice can affect the amount of income collected.  And it can leave a sour taste when the basket chosen is not the proper form.  In today’s Lesson, we learn how a taxpayer’s choice of business containers affects their ability to take deductions, and even affects their ability to litigate in Tax Court.

In Greatest Common Factor v. Commissioner, T.C. Memo. 2023-39 (Mar. 23, 2023) (Judge Kerrigan), the individual taxpayer chose to collect income through a C corporation and that choice affected the deductibility of the individual’s home office expenses.  In Techtron Holding, Inc. v. Commissioner, T.C. Memo 2023-29 (Mar. 9, 2023) (Judge Vasquez), the individual taxpayers collected income through ever-changing, multiple baskets of various kinds of business entities.  When the IRS audited and found deficiencies in one of the entities, the Tax Court decided it had no jurisdiction over that entity’s petition because the entity no longer existed at the time the petition was filed.  Details below the fold.

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Lesson From The Tax Court: The Whistleblower Who Blew Too Hard

Section 7623(b)(1) says that the IRS must reward whistleblowers when the information they provide causes the IRS to start “any administrative or judicial action” to collect unreported or unpaid taxes.  In such cases, whistleblowers can get an award of up to 30% of the proceeds actually collected from such actions.  Id.  So what happens if the whistleblower's information does not lead to an administrative or judicial action against the particular taxpayer fingered by the whistleblower, but instead prompts the IRS to create a general administrative program to target taxpayers like the one fingered by the whistleblower?

That was the claim in Thomas Shands v. Commissioner, 160 T.C. No. 5 (Mar. 8, 2023) (Judge Greaves).  There, the whistleblower claimed entitlement to 30% of some $1 billion collected from the IRS’s second Offshore Voluntary Disclosure Initiative (OVDI) in 2011.  His theory was that his blowing the whistle on one particularly influential tax evader prompted both the creation of the second OVDI and a rush by taxpayers to voluntarily disclose under the program.

The Tax Court ruled that Mr. Shands’ claim was overblown (pun totally intended).  Both the statute and implementing regulations make it clear that the relevant “administrative or judicial action” is one against particular identified taxpayers.  The creation of a general administrative program such as OVDI was not the kind of action that triggered a mandatory award.  Therefore, under the newly restricted reading of its authority to review whistleblower petitions, the Tax Court held that it lacked jurisdiction to review whether his information really did or did not contribute to OVDI.  The IRS simply had not started a requisite administrative or judicial action.  Details below the fold.

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Lesson From The Tax Court: Another Reason To Keep Good Records

Last week’s Lesson looked at the inherent unreliability of third-party information returns.  Taxpayers need to keep good records to refute those errors.  This week’s Lesson continues that theme: keeping good records can help avoid a bank deposits analysis.  When the IRS is forced to reconstruct income using the bank deposits method, it puts taxpayers in the hard place of having to prove why every bank deposit should not be counted as gross income for that year.

A pair of opinions issued by Judge Buch on the same day gives us a lesson on the unhappy consequences to taxpayers when their poor record-keeping leads the IRS to use a bank deposits method to reconstruct income.  In both Kevin B. Cheam and Julie Lim v. Commissioner, T.C. Memo. 2023-23 (Feb. 27, 2023), and Lundy Nath and Tanya Nath, T.C. Memo. 2023-22 (Feb. 27, 2023), the taxpayers’ failure to keep adequate books and records forced the IRS to conduct a bank deposits analysis, thus putting the burden on the taxpayers to show which bank deposits represented something other than gross income.  In neither case could the taxpayers show the Court nontaxable sources of income for the deposits the IRS asserted were unreported income.  And their record-keeping failures also hurt them in the usual way on the deduction side as well.  Details below the fold.

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Lesson From The Tax Court: The Inherent Unreliability Of Third-Party Reporting

Third-party reporting has long been crucial to tax administration.  Empirically, it helps taxpayers comply with their reporting duties.  Congress first starting requiring information returns in 1917 and keeps expanding the concept to reach new economic situations, such as the rise of the gig economy and on-line marketplaces.

But third-party information returns are inherently unreliable because they report payments, not income.  That is the lesson we learn in Tanisha Trice v. Commissioner, T.C. Memo. 2023-15 (Feb. 13, 2023) (Judge Gustafson).  In this case we learn the lesson with respect to Social Security Disability reporting.  There, the Form SSA-1099 reported payments to Ms. Trice of $15,365.  Judge Gustafson explains why that alone was not enough to support the Notice of Deficiency as to the payments that Ms. Trice denied receiving.  As to those, the IRS was required to produce additional evidence under §6201(d) because Ms. Trice had reasonably objected to that amount and had fully cooperated with the IRS.  Details below the fold.

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Lesson From The Tax Court: Fill Out The Damn Form

The fuss has focused on FBARs.  The FBAR requirements and penalty provisions have been hotly litigated.  Recently the Supreme Court issued an opinion in Bittner v. U.S., deciding that the penalties were not as harsh as the government thought they should be.

But forget FBAR.  Today’s lesson is about a different, yet equally important, foreign account reporting requirement: the one found in 26 U.S.C. §6048 that relates to foreign trusts.  The FBAR stuff is over in 31 U.S.C. §5314.  Completely different title.

And today’s lesson is not about penalties.  It’s about the assessment limitations period.  In Leigh C. Fairbank and Barbara J. Fairbank v. Commissioner, T.C. Memo. 2023-19 (Feb. 23, 2023) (Judge Weiler), we learn that a failure to comply with the §6048 reporting requirement by never filing the proper form---not even during audit---extends the time in which the IRS can assess really old tax deficiencies.  How old?  Try 15 years old.  Regardless of the outcome in Bittner, folks need to learn this lesson!  Details below the fold.

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Lesson From The Tax Court: The New Evidence Rule In Spousal Relief Cases

When a taxpayer requests spousal relief under §6015, the IRS must decide whether to grant it.  If the IRS denies relief, the taxpayer can petition the Tax Court. §6015(e).  In 2019 Congress created a modified administrative record rule for how the Tax Court is supposed to conduct that review.  Taxpayer First Act, 133 Stat. 981, 988.

It’s awkward.  Congress tells the Court to review the IRS decision de novo but, at the same time, tells the Court to do that using only a limited information set consisting of (a) “the administrative record established at the time of the determination” and (b) “any additional newly discovered or previously unavailable evidence.”  §6015(e)(7).

Sydney Ann Chaney Thomas v. Commissioner, 160 T.C. No. 4 (Feb. 13, 2023) (Judge Toro), is a reviewed opinion where a unanimous Tax Court interprets the phrase “newly discovered or previously unavailable evidence” broadly rather than narrowly, thus creating a new evidence rule (pun intended) that robustly protecting its ability to conduct the required de novo review.  Ironically, the decision worked against the taxpayer in this case because it was the IRS that here wanted to introduce new information (the taxpayer’s social media posts).  The taxpayer objected that those posts had been publicly available during the administrative proceeding; therefore they were not newly discovered or previously unavailable.  The Court rejected that argument and admitted the posts as evidence.

Today’s case is also an illustrative contrast to the T.C. opinion I discussed in last week’s post.  That was a case where the taxpayer was proceeding pro se.  And there the Court had no benefit of briefing from both sides.  I think the Court’s opinion showed it.  In today’s case, the taxpayer was (eventually) represented by one of the best tax attorneys I know, Megan Brackney.  Thus the Court had the benefit of a well-presented taxpayer argument.  The Court also had the benefit of a strong amicus brief submitted jointly by the Center for Taxpayer Rights, the Community Tax Law Project, the UC-SF LITC and the Villanova LITC.  That made the Tax Court’s opinion all the more robust, which is what it will need if and when its decision is reviewed in turn by a Court of Appeals.

Spoiler alert.  This post is a little longer than normal.  Sorry, Lew.

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Lesson From The Tax Court: The Limited Review Of Passport Revocation Certifications

Today’s lesson is about §7345, created by Congress in 2015.  The idea behind §7345 is simple.  If you owe taxes and the government threatens to take your passport, you are more likely to pay up.  But its operation is complex.  It requires the IRS to first certify to the State Department that a taxpayer has a “seriously delinquent tax debt.”  Then the State Department is authorized to take certain actions based on that certification.  Section 7345 permits taxpayers to seek Tax Court Review of IRS Certifications.

The Tax Court does not get many passport cases.  According to the Court’s FY 2024 Budget Request, of the 29,000 petitions filed in 2022, only 25 were §7345 petitions.  For those who are interested in learning more about the Court’s budget request, Keith Fogg posted this great review over on Procedurally Taxing.

So when the Tax Court gets a passport case, it often uses it to shape its §7345 jurisprudence by issuing precedential Tax Court opinions.  Today’s case is one of those. Blake M. Adams v. Commissioner, 160 T.C. No. 1 (Jan. 24, 2023) (Judge Toro), teaches two lessons.  First, the Court holds that it will not look behind the IRS certification to redetermine the merits of the tax liabilities that make up the certification.  Second, the Court also decides it lacks authority to determine whether the assessment underlying the Certification was procedurally defective.

Note that this is a case where the taxpayer was unrepresented.  While the Court’s desire to settle important §7345 issues is understandable, I question whether doing so in a pro-se case is desirable. Next week we will see a case where the Court wrote a much stronger opinion after first suggesting that the pro se taxpayer find counsel (who then filed briefed the issue) and also accepting an amicus brief. I offer my thoughts on this below the fold.

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