Clarifying Willfulness under the IEEPA: Knowledge of Unlawful Conduct without Specific Regulatory Awareness

Introduction

United States v. Jalal Hajavi, decided May 30, 2025 by the Eleventh Circuit Court of Appeals, addressed two central questions under the International Emergency Economic Powers Act (“IEEPA”):

1. What mens rea must the government prove to establish a “willful” IEEPA violation?
2. Was there sufficient evidence that the defendant knew his conduct—exporting U.S. heavy construction equipment to a United Arab Emirates (“UAE”) intermediary for onward shipment to Iran—was unlawful?

The appeal arose after a jury convicted Mr. Jalal Hajavi, an Iranian-born U.S. permanent resident and owner of JSH Heavy Equipment, LLC, on one count of conspiracy and two counts of substantive IEEPA violations, plus one count of smuggling. He challenged the district court’s jury instructions on mens rea and argued insufficient proof of his knowledge that shipments to the UAE would reach embargoed Iran.

Summary of the Judgment

The Eleventh Circuit unanimously affirmed. It held that:

• The district court did not err in refusing Hajavi’s proposed instruction requiring proof that he was “specifically aware” of 31 C.F.R. §§ 560.204 and 560.206 by number or text. Under United States v. Singer, 963 F.3d 1144 (11th Cir. 2020), willfulness under IEEPA requires knowledge of facts making the conduct unlawful, not necessarily familiarity with particular regulation citations.
• The jury instructions given—that the defendant acted “willfully,” i.e., “voluntarily and intentionally in violation of a known legal duty” and “knew that his conduct was unlawful”—adequately and accurately stated the law.
• Circumstantial and direct evidence (warnings by regulators, misleading billing practices, use of hawala payment, pattern of shipments to UAE free-trade‐zone intermediaries known as reexport points) permitted a reasonable jury to conclude beyond a reasonable doubt that Hajavi knew his equipment would be reexported to Iran in violation of IEEPA and its implementing Iranian Transactions and Sanctions Regulations (“ITSR”).

Analysis

1. Precedents Cited

The court’s reasoning rested principally on these key precedents:

• United States v. Singer, 963 F.3d 1144 (11th Cir. 2020): Established that willfulness under IEEPA requires proof that a defendant “knew the facts that made his conduct a violation of the law,” but does not demand the defendant have read or be expressly aware of the regulation’s section numbers or exact language. Evidence of “affirmative efforts” to warn the defendant or facts permitting inference of knowledge suffices.
• Ratzlaf v. United States, 510 U.S. 135 (1994): Emphasized that “willfulness” in complex regulatory contexts means knowing one’s conduct is unlawful; it is not triggered by mere negligence or ignorance of the law.
• Adames, 878 F.2d 1374 (11th Cir. 1989): Defined “willfully” as “voluntarily and intentionally in violation of a known legal duty.”
• Sotis, 89 F.4th 862 (11th Cir. 2023): Reinforced Singer’s mens rea standard for IEEPA-related prosecutions.
• En banc conspiracy decisions (e.g., United States v. Chandler, 388 F.3d 796 (11th Cir. 2004)): Established that conspiracy may be proved through circumstantial evidence and reasonable inferences.

2. Legal Reasoning

The court’s analysis unfolded in two stages:

1. Jury Instructions on Willfulness: Hajavi wanted an instruction that he must have been “specifically aware of” the ITSR by citation (31 C.F.R. §§ 560.204 & 560.206). The court declined, noting (i) under Singer, knowledge of statutory/regulatory facts may be proved circumstantially without requiring the defendant to recall or reference exact regulation numbers; (ii) the district court’s instruction—that the defendant acted “willfully” by violating a “known legal duty” and “knew his conduct was unlawful”—accurately tracked Eleventh Circuit law.
2. Sufficiency of Evidence: Viewing the record in the light most favorable to the government, the court identified multiple threads from which a rational jury could infer Hajavi’s knowledge:
   • 2009 administrative subpoena warning of export prohibitions.
   • August 2014 in-person meeting with a Commerce/Bureau of Industry and Security agent expressly informing him that shipments to UAE intermediaries destined for Iran required an OFAC license and that transshipment violations carried “ramifications.”
   • Repeated use of UAE free‐trade-zone general trading companies known as “transshipment diversion points” for embargoed goods.
   • False invoices and layered sales (JSH to trading company → trading company to Maghsoudi), and hawala payment transfers designed to conceal Iran’s involvement.

3. Impact on Future Cases

United States v. Hajavi reinforces and clarifies the mens rea requirements for IEEPA prosecutions in several ways:

• Defendants need not be shown to have memorized or read every relevant regulation number or paragraph. Prosecutors may rely on evidence of system­wide warnings, industry outreach visits, internal subpoenas, and circumstantial patterns of conduct to establish knowledge of unlawfulness.
• District courts may craft jury instructions that emphasize “knowledge that conduct is unlawful” rather than tying the defense to rote recall of regulatory citations.
• The decision underscores the Eleventh Circuit’s continued adherence to Singer and Ratzlaf: In complex export-control contexts, willfulness pivots on knowing facts that render the conduct illegal, not mere ignorance or reading of regulatory texts.
• In conspiracy contexts, it affirms that circumstantial proof of common purpose and “secretive” billing or payment practices can sustain convictions.

Complex Concepts Simplified

To aid understanding, below are explanations of key terms and doctrines:

• IEEPA (50 U.S.C. §§ 1701–07): Grants the President authority to regulate trade during declared national emergencies. Violations by “willful” conduct are criminal.
• ITSR (31 C.F.R. Part 560): Implements U.S. sanctions on Iran, prohibiting exports, re-exports, and any dealings that facilitate such transactions without an OFAC license.
• Willfulness: Requires voluntary and intentional violation of a known legal duty—that is, knowing one’s conduct is illegal, not merely negligent or mistaken.
• Transshipment/Third-Country Reexport: Routing U.S. goods through an intermediary country (e.g., UAE) before sending them to the embargoed destination (Iran). This practice is prohibited if done with knowledge of the final prohibited destination.
• Hawala System: An informal remittance network used to move money without formal banking channels—often employed to obscure the origin or destination of funds.
• Jury Instructions: Directions delivered by the judge explaining the law and elements the jury must find beyond a reasonable doubt before returning a guilty verdict.

Conclusion

United States v. Jalal Hajavi underscores a practical approach to mens rea under the IEEPA. A conviction for “willful” violations does not hinge on proof that a defendant has read or recited regulatory citations; it requires proof that the defendant knew the facts making his conduct illegal. The Eleventh Circuit confirms that clear warnings from regulators, pattern evidence of suspicious trade practices, and covert invoicing/payment schemes suffice to show knowledge. Going forward, this decision guides both prosecutors and defense counsel in framing evidence and jury charges in complex export-control and sanctions cases.