CIC Servs., LLC v. IRS, 593 U.S. 209

IRS Notice 2016–66 required taxpayers and "material advisors" to report certain "micro-captive" insurance transactions the IRS viewed as prone to tax abuse.
The Notice imposes affirmative, potentially substantial compliance costs and is backed by civil monetary penalties that the Code deems "taxes," plus separate criminal penalties for willful noncompliance.
CIC Services, a material advisor, filed a pre-enforcement APA challenge asking a court to set aside and enjoin enforcement of the Notice before any violation or penalty.
The Government moved to dismiss under the Anti‑Injunction Act (AIA), arguing CIC must pay any tax penalty first and sue for a refund; the District Court dismissed and the Sixth Circuit affirmed.
The Supreme Court reversed, holding the AIA does not bar CIC’s suit because the complaint targets the standalone reporting requirement (an independent regulatory duty), not the downstream tax‑collection process.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether the Anti‑Injunction Act bars a pre‑enforcement APA suit seeking to set aside IRS Notice 2016–66	CIC: suit challenges the Notice itself and seeks to set aside an independent reporting obligation, not to restrain tax assessment/collection	Govt: invalidating or enjoining enforcement of the Notice would prevent assessment/collection of the tax penalties that enforce it; AIA therefore bars the suit	Court: AIA does not bar the suit — the complaint and requested relief target the reporting rule, not the collection of a tax, for three reasons (independent compliance costs, attenuated chain to tax, and presence of criminal penalties)
Whether allowing CIC’s pre‑enforcement suit will broadly undermine the AIA by enabling pre‑enforcement tax challenges	CIC: ruling is narrow—applies where the suit targets an independent non‑tax regulatory obligation backed by tax penalties; ordinary tax challenges remain barred	Govt: decision will enable plaintiffs to bypass AIA by pleading non‑tax objections to measures that functionally impose taxes	Court: rejects floodgates concern; distinguishes suits attacking actual tax provisions (still barred) from suits attacking independent regulatory duties that happen to be backed by tax sanctions

Direct Marketing Assn. v. Brohl, 575 U.S. 1 (2015) (suits challenging reporting obligations are not necessarily suits to restrain tax assessment or collection)
Alexander v. "Americans United" Inc., 416 U.S. 752 (1974) (a suit’s purpose is determined by its objective aim and the relief requested)
Bob Jones Univ. v. Simon, 416 U.S. 725 (1974) (AIA bars pre‑enforcement suits that necessarily preclude tax assessment or collection)
Natl. Fed'n of Indep. Business v. Sebelius, 567 U.S. 519 (2012) (AIA protects government’s ability to collect revenue)
Cheek v. United States, 498 U.S. 192 (1991) (good‑faith belief about tax law validity does not negate willfulness for criminal tax violations)
Bailey v. George, 259 U.S. 16 (1922) (AIA can bar pre‑enforcement challenges to measures that function as taxes)