(Slip Opinion) OCTOBER TERM, 2020 1 

Syllabus 

NOTE: Where it is feasible, a syllabus (headnote) will be released, as is 

being done in connection with this case, at the time the opinion is issued. 

The syllabus constitutes no part of the opinion of the Court but has been 

prepared by the Reporter of Decisions for the convenience of the reader. 

See United States v. Detroit Timber & Lumber Co., 200 U. S. 321, 337. 

SUPREME COURT OF THE UNITED STATES 

Syllabus 

CIC SERVICES, LLC v. INTERNAL REVENUE 

SERVICE ET AL. 

CERTIORARI TO THE UNITED STATES COURT OF APPEALS FOR 

THE SIXTH CIRCUIT 

No. 19–930. Argued December 1, 2020—Decided May 17, 2021 

Internal Revenue Service (IRS) Notice 2016–66 requires taxpayers and 

“material advisors” like petitioner CIC to report information about certain insurance agreements called micro-captive transactions. The consequences for noncompliance include both civil tax penalties and criminal prosecution. Prior to the Notice’s first reporting deadline, CIC 

filed a complaint challenging the Notice as invalid under the Administrative Procedure Act and asking the District Court to grant injunctive

relief setting the Notice aside. The District Court dismissed the action 

as barred by the Anti-Injunction Act, which generally requires those 

contesting a tax’s validity to pay the tax prior to filing a legal challenge. A divided panel of the Sixth Circuit affirmed. 

Held: A suit to enjoin Notice 2016–66 does not trigger the Anti-Injunction Act even though a violation of the Notice may result in a tax penalty. Pp. 5–16. 

(a) The Anti-Injunction Act, 26 U. S. C. §7421(a), provides that “no 

suit for the purpose of restraining the assessment or collection of any 

tax shall be maintained in any court by any person.” Absent the tax 

penalty, this case would be easy: the Anti-Injunction Act would pose 

no barrier. A suit to enjoin a requirement to report information is not

an action to restrain the “assessment or collection” of a tax, even if the 

information will help the IRS collect future tax revenue. See Direct 

Marketing Assn. v. Brohl, 575 U. S. 1, 9–10. The addition of a tax penalty complicates matters, but it does not ultimately change the answer. 

Under the Anti-Injunction Act, a “suit[’s] purpose” depends on the action’s objective purpose, i.e., the relief the suit requests. Alexander v. 

“Americans United” Inc., 416 U. S. 752, 761. And CIC’s complaint

seeks to set aside the Notice itself, not the tax penalty that may follow 
 

 

 

 

 

2 CIC SERVS., LLC v. IRS 

Syllabus 

the Notice’s breach. The Government insists that no real difference 

exists between a suit to invalidate the Notice and one to preclude the

tax penalty. But three aspects of the regulatory scheme here refute 

the idea that this is a tax action in disguise. First, the Notice imposes 

affirmative reporting obligations, inflicting costs separate and apart 

from the statutory tax penalty. Second, it is hard to characterize CIC’s 

suit as one to enjoin a tax when CIC stands nowhere near the cusp of

tax liability; to owe any tax, CIC would have to first violate the Notice,

the IRS would then have to find noncompliance, and the IRS would 

then have to exercise its discretion to levy a tax penalty. Third, the 

presence of criminal penalties forces CIC to bring an action in just this

form, with the requested relief framed in just this manner. The Government’s proposed alternative procedure—having a party like CIC 

disobey the Notice and pay the resulting tax penalty before bringing a

suit for a refund—would risk criminal punishment. All of these facts, 

taken together, show that CIC’s suit targets the Notice, not the downstream tax penalty. Thus, the Anti-Injunction Act imposes no bar. Pp.

5–13. 

(b) Allowing CIC’s suit to proceed will not open the floodgates to preenforcement tax litigation. When taxpayers challenge ordinary taxes,

assessed on earning income, or selling stock, or entering into a business transaction, the underlying activity is legal, and the sole target

for an injunction is the command to pay a tax. In that scenario, the 

Anti-Injunction Act will always bar pre-enforcement review. And the 

analysis is the same for a challenge to a so-called regulatory tax—that 

is, a tax designed mainly to influence private conduct, rather than to

raise revenue. The Anti-Injunction Act draws no distinction between 

regulatory and revenue-raising tax laws, Bob Jones Univ. v. Simon, 

416 U. S. 725, 743, and the Anti-Injunction Act kicks in even if a plaintiff’s true objection is to a regulatory tax’s regulatory effect. By contrast, CIC’s suit targets neither a regulatory tax nor a revenue-raising

one; CIC’s action challenges a reporting mandate separate from any 

tax. Because the IRS chose to address its concern about micro-captive 

agreements by imposing a reporting requirement rather than a tax,

suits to enjoin that requirement fall outside the Anti-Injunction Act’s

domain. Pp. 13–15. 

925 F. 3d 247, reversed and remanded. 

KAGAN, J., delivered the opinion for a unanimous Court. SOTOMAYOR, 

J., and KAVANAUGH, J., filed concurring opinions. 
 

 

 

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Opinion of the Court 

NOTICE: This opinion is subject to formal revision before publication in the 

preliminary print of the United States Reports. Readers are requested to 

notify the Reporter of Decisions, Supreme Court of the United States, Washington, D. C. 20543, of any typographical or other formal errors, in order that 

corrections may be made before the preliminary print goes to press. 

SUPREME COURT OF THE UNITED STATES 

No. 19–930 

CIC SERVICES, LLC, PETITIONER v. INTERNAL 

REVENUE SERVICE, ET AL. 

ON WRIT OF CERTIORARI TO THE UNITED STATES COURT OF 

APPEALS FOR THE SIXTH CIRCUIT 

[May 17, 2021] 

JUSTICE KAGAN delivered the opinion of the Court. 

The Anti-Injunction Act, 26 U. S. C. §7421(a), bars any 

“suit for the purpose of restraining the assessment or collection of any tax.” The question here is whether the Act

prohibits a suit seeking to set aside an informationreporting requirement that is backed by both civil tax penalties and criminal penalties. We hold that the Act does not 

preclude the suit. 

I 

Americans have never had much enthusiasm for paying 

taxes. The Nation’s first income taxes—adopted to finance

the Civil War—met with considerable (one might even say

“taxing”) legal resistance. See Hickman & Kerska, Restoring the Lost Anti-Injunction Act, 103 Va. L. Rev. 1683, 

1723–1725 (2017). Some taxpayers, alleging the taxes illegal, sought to enjoin collection efforts. And some courts 

granted the requested relief. See, e.g., Roback v. Taylor, 20 

F. Cas. 852, 854 (No. 11,877) (CC SD Ohio 1866); Bank for 

Savings v. Collector, 3 Wall. 495 (1866). Those rulings disrupted the flow of revenue to the Federal Government. As 

one late-19th century treatise writer described the problem, 
 

 

2 CIC SERVS., LLC v. IRS 

Opinion of the Court 

“improvident employment of the writ of injunction” threatened to “seriously embarrass” tax-dependent “operations of 

the government.” T. Cooley, Law of Taxation 536–537 (2d 

ed. 1886).

Congress responded by enacting the Anti-Injunction Act.

See Act of Mar. 2, 1867, §10, 14 Stat. 475. In its current 

form (differing little from the original), the Act provides:

“[N]o suit for the purpose of restraining the assessment or 

collection of any tax shall be maintained in any court by any 

person.” 26 U. S. C. §7421(a). The Act, we have stated, 

“protects the [Federal] Government’s ability to collect a consistent stream of revenue, by barring litigation to enjoin or 

otherwise obstruct the collection of taxes.” National Federation of Independent Business v. Sebelius, 567 U. S. 519, 

543 (2012) (NFIB). Because of the Act, a person can typically challenge a federal tax only after he pays it, by suing 

for a refund. See ibid. 

In an ordinary Anti-Injunction Act case, that short primer on the statute would naturally bring us to a description

of the tax under dispute. But describing the tax implicated 

here will have to wait. For that tax—the thing that raises

the Anti-Injunction Act question—comes into play only at

the back end of a complex information-reporting scheme. 

The reporting scheme itself is where we must begin.

As every taxpayer knows, the Internal Revenue Service

(IRS) has broad power to require the submission of taxrelated information that it believes helpful in assessing and 

collecting taxes. See §6011(a). Those reporting rules may 

apply not just to taxpayers but also to “material advisors”—

individuals or entities that earn income from providing taxpayers with certain kinds of “aid, assistance, or advice.” 

§6111(b)(1)(A); see §6111(a). This case starts with requirements that taxpayers and material advisors provide detailed information about what the Internal Revenue Code 

calls “reportable transaction[s].” §6707A(c)(1). The Code 

describes those transactions simply as ones that “hav[e] a 
Cite as: 593 U. S. ____ (2021) 3 

Opinion of the Court 

potential for tax avoidance or evasion.” Ibid. Rather than 

give further specifics, the Code delegates to the Secretary 

of the Treasury, acting through the IRS, the task of identifying particular transactions with the requisite risk of tax 

abuse. See §§6011, 6707A(c)(1).

Using that authority, the IRS determined that so-called 

micro-captive transactions must be reported because of 

their potential for tax evasion. A micro-captive transaction 

is typically an insurance agreement between a parent company and a “captive” insurer under its control. The Code 

provides the parties to such an agreement with tax advantages. The insured party can deduct its premium payments as business expenses. See §162(a). And the insurer 

can exclude up to $2.2 million of those premiums from its

own taxable income, under a tax break for small insurance 

companies. See §831(b). The result is that the money does 

not get taxed at all. That much, for better or worse, is a 

congressional choice. But no tax benefit should accrue if 

the money is not really for insurance—if the insurance contract is a sham, which the affiliated companies have entered into only to escape tax liability. And according to the 

IRS, some micro-captive transactions are of that kind. So 

the IRS issued Notice 2016–66 identifying certain microcaptive agreements as reportable transactions. See 2016– 

47 Cum. Bull. 745. That Notice compels taxpayers and material advisors associated with such an agreement to

(among other things) “describe the transaction in sufficient

detail for the IRS to be able to understand [its] tax structure.” Id., at 748. With that information, the IRS can check 

for facts—like coverage for an “implausible risk” or premiums that “significantly exceed” prevailing rates—suggesting that the taxpayer is not entitled to the tax benefit it 

claims. Id., at 745–746. 

Noncompliance with Notice 2016–66 subjects a taxpayer

or material advisor to stiff penalties—at last bringing us to 

the tax involved in this case, as well as to non-tax criminal 
 

 

 

4 CIC SERVS., LLC v. IRS 

Opinion of the Court 

consequences. By statutory provision, all failures to supply 

required information on reportable transactions, including 

the micro-captive transactions specified in the Notice, are 

punishable by civil monetary penalties—$50,000 for advisors and up to that amount (depending on the amount of

tax gain realized) for taxpayers. See §§6707(b), 6707A(b).

In addition, an advisor may incur a daily $10,000 penalty 

for failing to furnish, on request, a list of the people it advised on a reportable transaction. See §§6708(a), 6112(a). 

And critically here, all those penalties are “deemed” to be 

“tax[es]” for purposes of the Code—including the AntiInjunction Act. §6671(a). So, again, the civil penalties for 

violating Notice 2016–66 are tax penalties, and must be 

treated as such. But no sooner do we find the tax appended 

to the Notice’s reporting scheme than we encounter something else. Under the Code, any person who “willfully” 

breaches an IRS reporting requirement is also subject to 

criminal penalties. §7203. Such a violation is a misdemeanor, punishable by fines and up to one year in prison.

And, unsurprisingly, that criminal liability is not “deemed” 

a tax. 

This suit challenges the lawfulness of Notice 2016–66.

The petitioner is CIC Services, a material advisor to taxpayers participating in micro-captive transactions. It 

brought this action before the Notice’s first reporting date, 

rather than after a reporting violation, let alone payment of 

penalty. (As far as we know, CIC has still not committed a 

violation, instead complying with the Notice while pressing

this suit.) CIC’s complaint mainly asserts that the IRS violated the Administrative Procedure Act (APA) by issuing 

the Notice without notice-and-comment procedures. The 

complaint also alleges that the Notice is arbitrary and capricious under the APA because it imposes new reporting

requirements without proven need. So the complaint asks

the court to “set[ ] aside IRS Notice 2016–66”—more specifically, to “enjoin the enforcement of Notice 2016–66 as an 
 

 

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Opinion of the Court 

unlawful IRS rule” and to “declar[e] that Notice 2016–66 is 

unlawful.” Complaint in No. 17–CV–110 (ED Tenn., Mar.

27, 2017), Doc. 1, pp. 2, 16 (Complaint).

But the suit has not yet proceeded to the merits. The 

Government moved to dismiss the action based on the AntiInjunction Act, arguing that CIC’s “requested relief would

prevent the IRS from assessing a tax penalty against material advisors” that disregard the Notice’s reporting requirements. Motion to Dismiss in No. 17–cv–110 (ED Tenn., 

May 30, 2017), Doc. 25–1, p. 9. In the Government’s view, 

the way for CIC to bring its claims is to disobey the Notice

and then sue for a refund of any resulting tax penalty. The 

District Court agreed. It reasoned that CIC’s suit sought

“to restrain the IRS’s assessment or collection” of the tax 

penalty that could be imposed for noncompliance. 2017 WL 

5015510, *4 (ED Tenn., Nov. 2, 2017). The Court of Appeals 

for the Sixth Circuit affirmed in a divided decision. According to the majority, CIC’s suit would “restrain (indeed eliminate)” the tax penalty by “invalidat[ing] the Notice, which

is [that tax’s] entire basis.” 925 F. 3d 247, 255 (2019). 

Judge Nalbandian dissented. “[T]his is not,” he wrote, “a 

dispute over taxes”: “[A] suit to enjoin the enforcement of a 

reporting requirement is not” one to restrain a tax’s collection. Id., at 259–260. Under the majority’s view, the dissent also objected, CIC could challenge the reporting

scheme only by “violat[ing] the law” and risking “criminal

prosecution.” Id., at 263. The Sixth Circuit denied a petition for rehearing en banc, over a dissent from seven judges.

We granted certiorari, 590 U. S. ___ (2020), and now reverse. 

II 

A 

The issue here, most concretely stated, is whether the 

Anti-Injunction Act bars CIC’s suit complaining that Notice 

2016–66’s reporting requirements violate the APA. Once 
 

 

 

6 CIC SERVS., LLC v. IRS 

Opinion of the Court 

again, the Anti-Injunction Act provides, with exceptions not 

relevant here, that “no suit for the purpose of restraining

the assessment or collection of any tax shall be maintained 

in any court by any person.” §7421(a). If CIC’s suit is not 

for that purpose, it can go forward. If the suit is for that 

purpose, it must be dismissed. In that event, CIC could contest the legality of the reporting rules only by violating 

them and suing for a refund of a later tax penalty. 

If that downstream tax penalty did not exist, this case

would be a cinch: The Anti-Injunction Act would not apply 

and the suit could proceed. A reporting requirement is not 

a tax; and a suit brought to set aside such a rule is not one 

to enjoin a tax’s assessment or collection. That is so even if 

the reporting rule will help the IRS bring in future tax revenue—here, by identifying sham insurance transactions.

See supra, at 3. We said as much in Direct Marketing Assn. 

v. Brohl, 575 U. S. 1 (2015).1 In that case, out-of-state retailers wanted to invalidate a Colorado law requiring them

to report to the State’s Department of Revenue any sale to

a state resident on which they had not collected tax. We 

allowed the suit to proceed, explaining that a suit about reporting requirements is not about the “assessment” or “collection” of taxes. Id., at 9–10. “Information gathering,” we

stated, is “a phase of tax administration procedure that occurs before assessment [or] collection.” Id., at 8. And it did 

not matter that the reporting requirements would “facilitate collection of taxes”—there, by identifying residents 

who owed sales taxes. Id., at 12. The statute’s limit on injunctions, we said, is “not keyed to all activities that may

improve a State’s ability to assess and collect taxes.” Id., at 

—————— 1 Direct Marketing construed the Tax Injunction Act—a statute, “modeled on the Anti-Injunction Act,” that limits injunctive relief against state 

tax collection. 575 U. S., at 8. This Court has “assume[d] that words 

used in both Acts,” such as “assessment” and “collection,” are “generally 

used in the same way.” Ibid. 
 

Cite as: 593 U. S. ____ (2021) 7 

Opinion of the Court 

11. It is instead “keyed to the acts of assessment [and] collection themselves.” Id., at 12. That means a suit directed 

at ordinary reporting duties can go forward, unimpeded by 

the Anti-Injunction Act. On this much, even the Government agrees. See Brief for Respondents 27.

The complication here is that Notice 2016–66’s reporting

obligations (unlike those in Direct Marketing) are backed 

up by a statutory tax penalty. As earlier described, the 

Code provides that a taxpayer who violates a demand for 

information about a reportable transaction—including 

those specified in the Notice—is subject to civil monetary

penalties. See supra, at 3–4. And the Code “deem[s]” those

civil penalties to be “tax[es]” as the Anti-Injunction Act uses

that term. §6671(a); see NFIB, 567 U. S., at 544 (“Congress

can, of course,” direct that a penalty “be treated as a tax for 

purposes of the Anti-Injunction Act”). The question thus

becomes whether that added tax penalty changes the analysis. Does its presence—as a sanction for flouting the Notice—mean that CIC’s suit is, as the Anti-Injunction Act 

provides, “for the purpose of restraining the assessment or 

collection of any tax”?

In considering a “suit[’s] purpose,” we inquire not into a

taxpayer’s subjective motive, but into the action’s objective 

aim—essentially, the relief the suit requests. The parties

agree on that interpretation, as both consistent with the

Act’s ordinary meaning and necessary for the Act’s administration. See Brief for Respondents 40; Reply Brief 4; Tr.

of Oral Arg. 15, 34. The purpose of a measure is “the end

or aim to which [it] is directed.” N. Webster, An American 

Dictionary of the English Language (rev. ed. 1844); see 

Webster’s Third New International Dictionary 1847 (1976). 

And in this context, that aim is not best assessed by probing 

an individual taxpayer’s innermost reasons for suing.

Down that path lies too much potential for circumventing

the Act. Instead, this Court has looked to the face of the 

taxpayer’s complaint. See, e.g., Bob Jones Univ. v. Simon, 
 

 

8 CIC SERVS., LLC v. IRS 

Opinion of the Court 

416 U. S. 725, 738 (1974). We have asked about what the 

Government here calls “the substance of the suit”—the 

claims brought and injuries alleged—to determine the 

suit’s object. Brief for Respondents 40. And most especially, we have looked to the “relief requested”—the thing

sought to be enjoined. Alexander v. “Americans United” 

Inc., 416 U. S. 752, 761 (1974); see Bob Jones, 416 U. S., at 

732 (“[A] suit seeking [injunctive] relief ” against a tax “falls

squarely within the literal scope of the Act”). The AntiInjunction Act kicks in when the target of a requested injunction is a tax obligation—or stated in the Act’s language,

when that injunction runs against the “collection or assessment of [a] tax.”

It is in characterizing the purpose of CIC’s suit that the

parties’ disagreement emerges. Recall that CIC’s complaint

avers that Notice 2016–66 violates the APA. See supra, at 

4–5. And the complaint describes the relief requested as

“setting aside IRS Notice 2016–66,” “enjoin[ing] the enforcement of Notice 2016–66 as an unlawful IRS rule,” and 

“declaring that Notice 2016–66 is unlawful.” Complaint 2,

16. According to CIC, all of that reveals the suit’s aim as 

invalidating the Notice and thereby eliminating its onerous 

reporting requirements—not as blocking the downstream

tax penalty that may sanction the Notice’s breach. See Reply Brief 6. By contrast, the Government contends that the

suit’s purpose is to stop the collection of the tax itself. See 

Brief for Respondents 12. In making that claim, the Government picks up on the word “enforcement” in CIC’s request for relief: Because the Notice is enforced through tax 

penalties, the Government claims, “enjoin[ing] the [Notice’s] enforcement,” as CIC wants, means preventing the 

IRS from collecting taxes. Id., at 23, 37–38. And even putting aside that word, the Government insists that there is

no real difference between a suit to invalidate the Notice 

and one to preclude the tax penalty. See id., at 38; Tr. of 

Oral Arg. 54–56. Avoiding the burdens of compliance with 
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Opinion of the Court 

the Notice and avoiding the tax that sanctions noncompliance, the Government asserts, are “two sides of the same 

coin.” Brief for Respondents 37. The Government thus suggests that by framing this suit as an attack on the Notice, 

CIC is trying to “eva[de] the Anti-Injunction Act through 

artful pleading.” Id., at 38. 

To begin with, we agree with CIC’s reading of its complaint. The complaint contests the legality of Notice 2016–

66, not of the statutory tax penalty that serves as one way 

to enforce it. CIC alleges that the Notice is procedurally

and substantively flawed; it brings no legal claim against 

the separate statutory tax. And CIC’s complaint asks for

injunctive relief from the Notice’s reporting rules, not from 

any impending or eventual tax obligation. Contra the Government’s view, a request in an APA action to “enjoin the

enforcement” of an IRS reporting rule is most naturally understood as a request to “set aside” that rule (as the complaint elsewhere says), not to block the application of a penalty that might be imposed for some yet-to-happen 

violation. 5 U. S. C. §706; Complaint 2, 9, 16. Indeed, CIC’s 

complaint barely mentions that penalty. The complaint,

and particularly its request for relief, sets out this suit’s

purpose as enjoining the Notice.

And we reject the Government’s argument that an injunction against the Notice is the same as one against the tax

penalty—just “two sides of the same coin.” Brief for Respondents 37. If that view were right, of course, no amount

of artful pleading would avail: CIC’s suit targeting the Notice would then in fact target the tax, and the AntiInjunction Act would apply. But the Government’s take is 

wrong. Three aspects of the regulatory scheme here, taken 

in combination, refute the idea that this is a tax action in 

disguise. They show that in addressing Notice 2016–66, 

this suit (and any resulting injunction) addresses something other than the tax penalty helping to back it up. 
 

 

 

10 CIC SERVS., LLC v. IRS 

Opinion of the Court 

First, the Notice imposes affirmative reporting obligations, inflicting costs separate and apart from the statutory

tax penalty. As described earlier, the Notice levies no tax. 

Rather, it compels taxpayers and their material advisors to

collect and submit detailed information about micro-captive

transactions and their participants. See supra, at 3. And 

obeying that mandate is likely to involve significant time 

and expense. Here, for example, CIC estimates that it will 

have to spend “hundreds of hours of labor and in excess of 

$60,000 per year” to comply with the Notice. See Complaint

¶40. Costs of that kind may well exceed, or even dwarf, the 

tax penalties for a violation. So in bringing this suit, CIC 

challenges a regulatory mandate that (1) is not a tax and 

(2) entails compliance costs whose amount is not tied to, 

and often goes beyond, any tax. Simply stated, this suit attempts to get out from under the (non-tax) burdens of a 

(non-tax) reporting obligation. Of course, if the suit succeeds, CIC will never have to worry about the tax penalty; 

once the reporting duty disappears, the sanction becomes 

irrelevant. But that is the suit’s after-effect, not its substance. The suit still targets the reporting mandates—the 

independently onerous reporting mandates—of the Notice

itself. 

Second and relatedly, the Notice’s reporting rule and the

statutory tax penalty are several steps removed from each

other. Consider what has to happen before CIC owes taxes 

to the IRS. To start, CIC has to withhold required information about a micro-captive transaction that the Notice 

covers. (And note, for whatever it is worth, that CIC disclaims any intent to do so while the Notice remains the law.

See Brief for Petitioner 29.) Next, the IRS must determine 

(often no small matter) that a violation of the Notice has in

fact occurred. And finally, the IRS must make the—entirely discretionary—decision to impose a tax penalty. See 

§6707A(d). If and only if all those things occur does tax li-
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Opinion of the Court 

ability attach. That threefold contingency matters in assessing whether the Anti-Injunction Act applies. Even the 

Government concedes that when there is “too attenuated a 

chain of connection” between an upstream duty and a

“downstream tax,” a court should not view a suit challenging the duty as aiming to “restrain the assessment or collection of a tax.” Tr. of Oral Arg. 38–39.2 That principle

favors CIC here. CIC stands nowhere near the cusp of tax 

liability: Between the upstream Notice and the downstream 

tax, the river runs long. So it is again hard to characterize 

this suit’s purpose as enjoining a tax.

Third, violation of the Notice is punishable not only by a

tax, but by separate criminal penalties. As noted above, 

any “[w]illful failure” to comply with the Notice’s reporting 

rules can lead to as much as a year in prison. §7203; see 

supra, at 3–4. That fact clinches the case for treating a suit

brought to set aside the Notice as different from one

brought to restrain its back-up tax. For the existence of 

criminal penalties explains why an entity like CIC must

bring an action in just this form, framing its requested relief in just this way. Recall what the Government would 

—————— 2The Government’s own example proves our point. Environmental 

Protection Agency (EPA) regulations governing the resale of diesel fuel

are enforced in part through a penalty that Congress has deemed a tax,

in just the way it has the penalty here. See §§6720A(a), 6671(a). The 

Government concedes that “a court might well conclude” that a suit to

enjoin the enforcement of the EPA regulations is “not one ‘for the purpose

of restraining’ tax assessment or collection, even if ” a ruling for the 

plaintiff would “have an eventual downstream impact on the IRS’s collection of the [tax] penalty.” Brief for Respondents 44. But that example 

is no different from this case, save that here the IRS, not the EPA, administers the regulatory mandate. And that one variance should not 

matter. As explained above, an IRS reporting requirement absent a tax

penalty no more triggers the Anti-Injunction Act than an EPA rule does. 

See Direct Marketing Assn. v. Brohl, 575 U. S. 1, 11–12 (2015); supra, at 

6–7. So adding an identical tax penalty to each of those regulatory 

schemes should affect the Anti-Injunction Act analysis in the same

way—which is to say, not at all. 
 

 

 

12 CIC SERVS., LLC v. IRS 

Opinion of the Court 

have such a party do: disobey the Notice, pay a resulting

tax penalty, and then bring a refund suit. See Brief for Respondents 16–17; supra, at 5. That approach—not the AntiInjunction Act’s familiar pay-now-sue-later procedure, but 

one with lawbreaking at the start—subjects the party to 

criminal punishment.3 And that is not the kind of thing an

ordinary person risks, even to contest the most burdensome 

regulation. So the criminal penalties here practically necessitate a pre-enforcement, rather than a refund, suit—if 

there is to be a suit at all. And so too, those penalties necessitate a suit aimed at eliminating the Notice, rather than 

the statutory tax penalty. Only an injunction against the

Notice gives the taxpayer or advisor what it wants: relief 

from the obligation to report transactions. An injunction

against the tax penalty would not do so. Because such an 

injunction would leave both the reporting duty and the

criminal penalty untouched, the taxpayer or advisor would

still have to accede to the Notice’s demands on pain of

prison time. Small wonder that CIC’s complaint asks for

an injunction against the Notice, not one against the tax

penalty helping to enforce it. Contrary to the Government’s

assertion, those injunctions are not two sides of one coin.

For all these reasons, the purpose of CIC’s suit is not to 

—————— 3The Government suggests that criminal liability would not attach to 

a taxpayer or advisor who refuses to comply with the Notice out of a “good

faith” objection to its validity. Brief for Respondents 46. It is easy to see 

why the Government wishes that were true: In none of our AntiInjunction Act cases has postponing a taxpayer’s suit until after payment 

exposed him to criminal penalties—because in no other case has that approach required a taxpayer to break a law in the first instance. But this 

Court’s precedent precludes the Government’s effort to erase the criminal penalties from this case. We have held in no uncertain terms that “a 

defendant’s views about the validity” of a tax provision—even if held “in

good faith”—do not “negate[ ] willfulness or provide[ ] a defense to criminal prosecution.” Cheek v. United States, 498 U. S. 192, 204, 206 (1991).

So in failing to report transactions as the Notice requires, an advisor like

CIC would risk criminal punishment. 
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Opinion of the Court 

“restrain[ ] the assessment or collection of [a] tax.” 

§7421(a). The complaint, and particularly the relief sought,

targets the Notice’s reporting rule, asking that it be set 

aside as a violation of the APA. And nothing in that request

smacks of artful pleading. To the contrary. That the Notice 

imposes an affirmative duty independent of the tax, entailing its own substantial costs; that the Notice and tax may 

remain forever divorced, depending on both CIC’s and the 

IRS’s choices; that not only the tax but also criminal penalties backstop the Notice—these facts, when combined, readily explain why CIC’s suit targets the upstream reporting

mandate, not the downstream tax. And because that is the 

suit’s aim, the Anti-Injunction Act imposes no bar. 

B 

The Government worries that a ruling for CIC will enfeeble the Anti-Injunction Act. If CIC can bring this suit now, 

the Government claims, a wave of pre-enforcement actions 

will follow. Canny plaintiffs will assert non-tax reasons (including objections to regulatory demands) for contesting the

imposition of taxes. See Brief for Respondents 32, 38. And 

in that way, taxpayers will obtain just what the AntiInjunction Act is meant to foreclose—orders “preemptively

shield[ing]” their activities or transactions from “tax consequences.” Id., at 13. More and more, the Government 

warns, tax litigation will shift from refund actions to preenforcement suits. And the IRS’s ability to assess and collect taxes will decline in proportion. 

The Government, however, much overstates the possible

consequences of today’s ruling. As we have explained, this

suit falls outside the Anti-Injunction Act because the injunction it requests does not run against a tax at all. See 

supra, at 9–13. The suit contests, and seeks relief from, a 

separate legal mandate; the tax appears on the scene—as

criminal penalties do too—only to sanction that mandate’s

violation. Or as Judge Nalbandian put the point below: 
 

14 CIC SERVS., LLC v. IRS 

Opinion of the Court 

“[T]his is not a dispute over taxes.” 925 F. 3d, at 259; see 

supra, at 5. By contrast, the kind of case the Government 

invokes in making its floodgates claim is a conflict over 

taxes, whether on earning income, or selling stock, or entering into a business transaction. In such a case, the legal

rule at issue is a tax provision. The tax does not backstop 

the violation of another law that independently prohibits or 

commands an action. Instead, the tax imposes a cost on

perfectly legal behavior. So there is no target for an injunction other than the command to pay the tax; there is no nontax legal obligation to restrain. Given that fact, the AntiInjunction Act bars pre-enforcement review, prohibiting a 

taxpayer from bringing (as the Government fears) a 

“preemptive[ ]” suit to foreclose tax liability. Brief for Respondents 13. And it does so always—whatever the taxpayer’s subjective reason for contesting the tax at issue. If 

the dispute is about a tax rule—as it is in the run-of-themine suits the Government raises—the sole recourse is to 

pay the tax and seek a refund. 

That is just as true when the tax in question is a so-called

regulatory tax—that is, a tax designed mainly to influence 

private conduct, rather than to raise revenue. This Court 

has long since “abandoned the view that bright-line distinctions exist between regulatory and revenue-raising taxes.” 

Bob Jones, 416 U. S., at 743, n. 17; see id., at 741, n. 12; 

Sonzinsky v. United States, 300 U. S. 506, 513 (1937) 

(“Every tax is in some measure regulatory”). And for just

as long, we have rejected the view that regulatory tax cases 

have a special pass from the Anti-Injunction Act. A century

ago, the Court in Bailey v. George, 259 U. S. 16 (1922), held 

that the Act barred a pre-enforcement suit challenging a

tax intended to discourage the (then lawful) use of child labor. Some 50 years later, the Court in Bob Jones and Americans United similarly held that the Act barred preenforcement suits challenging IRS decisions to revoke the 
 

 

Cite as: 593 U. S. ____ (2021) 15 

Opinion of the Court 

tax-exempt status of entities that had engaged in, respectively, discriminatory conduct and lobbying activity—conduct that was legal but disfavored for tax purposes. See 416 

U. S., at 735; 416 U. S., at 755. In doing so, the Court made 

clear that the plaintiffs’ reasons for suing did not matter: It

was, for example, irrelevant that Bob Jones University objected to the IRS’s “attempt to regulate the admissions policies of private universities.” 416 U. S., at 739. Nor did it 

matter that the tax ruling was in truth an effort to change 

those policies. Regardless of those facts, the suits sought to 

prevent the levying of taxes, and so could not go forward.

The Anti-Injunction Act, we said then and say again now, 

draws no distinction between regulatory and revenueraising tax rules. It applies whenever a suit calls for enjoining the IRS’s assessment and collection of taxes—of 

whatever kind. 

What sets this suit apart is that it no more targets a regulatory tax than a revenue-raising one. One last time: 

CIC’s action challenges, in both its substantive allegations 

and its request for an injunction, a regulatory mandate—a 

reporting requirement—separate from any tax. Or said 

otherwise, the suit targets not a regulatory tax, but instead 

a regulation that is not a tax. Here, the tax functions, 

alongside criminal penalties, only as a sanction for noncompliance with the reporting obligation. Had Congress, or the 

IRS acting through a delegation, imposed a tax on microcaptive transactions themselves—and had CIC then 

brought a pre-enforcement suit to prevent the IRS from applying that tax—the Anti-Injunction Act would have kicked

in. Then, CIC would have had to pay the tax and seek a 

refund. But Congress and the IRS chose a different path.

They imposed a non-tax, reporting obligation to address

their concerns about micro-captive agreements. And by

that choice, they took suits to enjoin their regulatory response outside the Anti-Injunction Act’s domain. 
 

16 CIC SERVS., LLC v. IRS 

Opinion of the Court 

III 

CIC’s suit aims to enjoin a standalone reporting requirement, whose violation may result in both tax penalties and 

criminal punishment. That is not a suit “for the purpose of 

restraining the [IRS’s] assessment or collection” of a tax,

and so does not trigger the Anti-Injunction Act. We reverse 

the judgment below and remand the case for further proceedings consistent with this opinion. 

It is so ordered. 
_________________ 

_________________ 

Cite as: 593 U. S. ____ (2021) 1 

SOTOMAYOR, J., concurring 

SUPREME COURT OF THE UNITED STATES 

No. 19–930 

CIC SERVICES, LLC, PETITIONER v. INTERNAL 

REVENUE SERVICE, ET AL. 

ON WRIT OF CERTIORARI TO THE UNITED STATES COURT OF 

APPEALS FOR THE SIXTH CIRCUIT 

[May 17, 2021] 

JUSTICE SOTOMAYOR, concurring. 

I concur because I agree that CIC Services, a material advisor to taxpayers engaged in micro-captive transactions,

does not bring this suit “for the purpose of restraining the

assessment or collection of any tax,” 26 U. S. C. §7421(a), 

but rather for the purpose of avoiding the regulatory burdens imposed by Notice 2016–66 (Notice). The three factors 

identified by the majority, taken in combination, show that 

this suit falls outside the ambit of the Anti-Injunction Act 

(AIA): The Notice imposes substantial compliance costs

that are unconnected to (and possibly far greater than) CIC 

Services’ potential tax liability; the causal chain connecting 

the Notice’s reporting requirement to any tax is attenuated; 

and the Notice is enforced by criminal as well as tax penalties. See ante, at 9–13. 

I write separately to highlight that the answer might be 

different if CIC Services were a taxpayer instead of a tax 

advisor. Taxpayers who are subject to reporting requirements backed by tax penalties face a choice: (1) provide information about their own finances to the Internal Revenue 

Service (IRS), which may in turn use that information to

calculate the taxpayers’ liability more accurately, or (2) refuse to provide such information and pay a noncompliance 

penalty, which Congress has deemed a tax. For a given taxpayer, then, a tax on noncompliance may operate as a rough 
 

2 CIC SERVS., LLC v. IRS 

SOTOMAYOR, J., concurring 

substitute for the tax liability she has evaded by withholding required information. Moreover, compared with their

tax advisors, taxpayers may incur less expense in collecting

and reporting their own financial information. Such information, after all, is about those taxpayers’ own activities

and is likely to be in their possession. Hence, while it will 

often be correct to conclude that a tax advisor challenging 

an IRS reporting requirement is not doing so “for the purpose of restraining” a tax on noncompliance, the analysis

may be different when it comes to taxpayers.

This case provides no occasion for the Court to inquire 

into the full quantity or variety of IRS reporting requirements that are backed by tax penalties, nor to predetermine

whether the AIA would allow hypothetical taxpayers to

challenge those requirements in court. Whether such suits 

may proceed will depend on a context-specific inquiry into 

“the relief the suit requests” and the “aspects of the regulatory scheme” at issue. Ante, at 7, 9. On that understanding, 

I concur. 
 

 

_________________ 

_________________ 

Cite as: 593 U. S. ____ (2021) 1 

KAVANAUGH, J., concurring 

SUPREME COURT OF THE UNITED STATES 

No. 19–930 

CIC SERVICES, LLC, PETITIONER v. INTERNAL 

REVENUE SERVICE, ET AL. 

ON WRIT OF CERTIORARI TO THE UNITED STATES COURT OF 

APPEALS FOR THE SIXTH CIRCUIT 

[May 17, 2021] 

JUSTICE KAVANAUGH, concurring. 

I join the Court’s opinion in full. I write separately to

underscore what remains (and does not remain) of Alexander v. “Americans United” Inc., 416 U. S. 752 (1974), and 

Bob Jones Univ. v. Simon, 416 U. S. 725 (1974), in the wake

of the Court’s decision today.

In Americans United and Bob Jones, this Court adopted

a straightforward and broad rule for determining whether

a pre-enforcement suit is barred by the Anti-Injunction Act.

Under that rule, if a pre-enforcement suit would “necessarily preclude” the assessment or collection of a tax, that

suit is barred by the Act and the taxpayer needs to bring a

refund suit after paying the tax. Bob Jones, 416 U. S., at 

732; see also Americans United, 416 U. S., at 760–761. In 

other words, Americans United and Bob Jones instruct 

courts to look to the effects of a suit. And if a pre-enforcement suit would have the effect of preventing the assessment or collection of a tax, then that suit is barred by the 

Anti-Injunction Act.

Many courts have taken Americans United and Bob Jones 

at their word. And the Sixth Circuit did so here. In this 

case, CIC challenged a regulation that was backed by tax

penalties—more specifically, penalties that the Tax Code

labels as “taxes” for purposes of the Anti-Injunction Act. 
 

2 CIC SERVS., LLC v. IRS 

KAVANAUGH, J., concurring 

See 26 U. S. C. §6671(a). Because invalidating the regulation at issue would “necessarily preclude” the collection of

tax penalties (labeled as “taxes” by the Tax Code) stemming

from an individual’s violation of that regulation, the Sixth

Circuit concluded that CIC’s pre-enforcement suit was

barred by the Anti-Injunction Act under Americans United 

and Bob Jones. That was a reasonable conclusion to reach, 

especially given that CIC’s primary argument here is the

same basic argument that this Court rejected in both Americans United and Bob Jones. Compare Brief for Respondent 

in Alexander v. “Americans United” Inc., O. T. 1973, No. 72– 

1371, p. 25 (It “is clear that the ‘purpose’ of this law suit” 

“is not to restrain the assessment or collection of any tax

but to challenge the constitutionality of an essentially regulatory Act of Congress”), with Brief for Petitioner 17 (“The

purpose of CIC’s suit” “is to avoid the burdens of the reporting requirement—not to avoid or dispute any tax liability”).

The Court today holds, however, that CIC’s pre-enforcement suit is not barred by the Anti-Injunction Act. In so 

holding, the Court in effect carves out a new exception to 

Americans United and Bob Jones for pre-enforcement suits

challenging regulations backed by tax penalties. I agree

with the Court’s decision to narrow Americans United and 

Bob Jones because the broad “effects” rule articulated in 

those decisions is hard to square with the text of the AntiInjunction Act, which bars only a pre-enforcement “suit for

the purpose of restraining the assessment or collection of 

any tax.” §7421(a). Contrary to some sweeping language 

in Americans United and Bob Jones, the Anti-Injunction

Act is best read as directing courts to look at the stated object of a suit rather than the suit’s downstream effects. See 

ante, at 7–8. And for that reason, as the Court explains, the 

text of the Anti-Injunction Act is best read as distinguishing

(i) pre-enforcement suits challenging the regulatory component of a regulatory tax, which remain prohibited because 
Cite as: 593 U. S. ____ (2021) 3 

KAVANAUGH, J., concurring 

the requested relief necessarily runs against the assessment or collection of a tax, from (ii) pre-enforcement suits 

challenging a regulation backed by a tax penalty, which

may proceed because the requested relief runs against an

independent legal obligation. 

In short, as I understand the Court’s opinion today, the

rule going forward is that pre-enforcement suits challenging regulatory taxes or traditional revenue-raising taxes

are still ordinarily barred by the Anti-Injunction Act. But 

pre-enforcement suits challenging regulations backed by 

tax penalties are ordinarily not barred, even though those 

suits, if successful, would necessarily preclude the collection or assessment of what the Tax Code refers to as a tax. 

With those observations, I join the Court’s opinion in full.