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OFAC Masterclass 2022

Advanced OFAC training designed for those with targeted OFAC compliance duties in industry and finance in the post screening phase.

A step-by-step methodology for determining whether transactions are prohibited, exempt, licensed or sanctionable under OFAC-administered laws.


OFAC-administered provisions are often ambiguous and open to a range of interpretations. Even in cases where professionals know that a given type of transaction is prohibited, it can be difficult to explain why, in technical terms, the transaction is prohibited. This course provides an analytical framework for determining whether a transaction is prohibited, licensed, exempt or otherwise “sanctionable” under OFAC regulations and programs. The course addresses the four main groups of OFAC-administered sanctions programs in separate sessions so that, in total, the entirety of the OFAC sanctions architecture is covered.

Learning Objectives

Learn the operation of OFAC regulations at the root level

Know when and why a blocking or other OFAC prohibition applies to a certain transaction or business dealing

Know a structured methodology for approaching OFAC issues involving common and irregular provisions

Understand the analytical framework for addressing “secondary sanctions” problems

Learn how to answer “easy” questions from the business in a more disciplined fashion.

Target Audience

Sanctions professionals with targeted OFAC compliance duties in industry and finance in the post-screening phase.

External and in-house attorneys tasked with addressing OFAC-related questions


Instructor-led class using case-based learning

Interactive live online program with breakout sessions in smaller groups

Contains reading assignments and a test.

Reading Assignment

Virtual Class 1 and Reading Assignment

Virtual Class 2 and Reading Assignment

Virtual Class 3 and Reading Assignment

Virtual Class 4



The Course is taken over a period of 6 weeks and is 12 hours total

4 sessions of 2 hours each (one session per week)

45 minute-reading assignments, prior to each class

1 hour exam

System Requirements

OFAC Masterclass is compatible with most operating systems and browsers to make it easy for everyone to participate. The course uses

Goto Training from Citrix

Litmos or other Learning Management System (LMS)

Upcoming Virtual Sessions

2022 Fall Session

  • Oct  6, 2022 – Course becomes available
  • Oct 12, 2022 – 1st Virtual Class (10:00–12:00 ET)
  • Oct 19, 2022 – 2nd Virtual Class (10:00–12:00 ET)
  • Oct 26, 2022 – 3rd Virtual Class (10:00–12:00 ET)
  • Nov   2, 2022 – 4th Virtual Class (10:00–12:00 ET)


ACSS Members


Non-ACSS Members


If you have multiple team members who can benefit from this program or wish to talk about enterprise packages, please contact for pricing and more information:

How it is structured?

Virtual Class 1: Fundamentals of the OFAC-administered Sanctions Architecture and the Basic Blocking Prohibition

In this class we review the fundamentals of the OFAC-administered sanctions architecture, identifying and discussing the relationships between sources of law (e.g. regulations and statutes) and auxiliary sources of information and authority (e.g. guidance and FAQs). The second part of the session focuses on the scope and application of the basic blocking prohibition, which appears in dozens of different OFAC sanctions programs and accounts for a substantial portion of the OFAC-administered sanctions architecture. With few exceptions, it is interpreted and applied consistently across programs, and mastery of the blocking prohibition aids with virtually all other types of OFAC-related questions. We first address the question of whether the blocking prohibition applies to a given transaction as a threshold question, breaking the analysis into a series of discrete questions:

  • Question 1: Does the transaction involve a “U.S. person” or other person subject to OFAC’s jurisdiction?
  • Question 2: Does the transaction involve one or more blocked persons? (E.g. SDNs, persons blocked pursuant the 50% rule, persons “controlled” by blocked governments).
  • Question 3: Does the transaction entail a direct or indirect “dealing” in “property” in which a blocked person has an “interest”? (Or “facilitation” thereof?)
  • Question 4: Does the transaction entail the provision/receipt of funds, goods or “services” to or from a blocked person? (Or “facilitation” thereof?)
Virtual Class 2: Territory-based Embargo Programs: Common General Licenses and Exemptions (2 hours)

In this class we build on the lessons learned in Class 1 and address the scope and operation of the standard, non-blocking IEEPA-based embargo programs (Iran, Syria, North Korea, Crimea).

  • The determination of whether a non-blocked person is subject to an applicable prohibition (i.e. the question of whether an person is “in” or “ordinarily resident in” a sanctioned territory)
  • The application of the cross-programmatic prohibitions on the “import” and “export” of “services” and “goods”; the “new investment” prohibition
  • The peculiarities of the Syria program (e.g., no import prohibition, exports governed by Commerce)
  • The peculiarities of the Cuba program (e.g., expansive jurisdiction; all nationals are “blocked”; prohibitions on dealing in Cuban-origin items)
  • The peculiarities of the Iran program (e.g., expansive jurisdiction; prohibition on dealings in Iranian-origin goods and services)

We also address the most popular general licenses and exemptions that apply, in a similar fashion, across multiple embargo programs and generally exclude SDNs:

  • The standard “noncommercial, personal remittances” GLs
  • Issues involving the operation and maintenance of accounts for sanctioned individuals
  • Exportation of communications-related services and goods
  • The “publishing” GLs
  • The mail and telecommunications GLs
  • Agricultural/medical-related GLs
  • GLs and exemptions for the “official business” of the U.S. government; United Nations and others
  • The travel exemption
  • The exemptions for personal communications and “information and informational materials”
Virtual Class 3: Irregular Non-embargo Primary Sanctions Programs and Methodologies for Addressing Questions Involving OFAC’s “Gray Areas” (2 hours)
This first part of this class covers the aspects of OFAC-administered primary sanctions architecture addressed above, and focuses primarily on the country-focused programs of particular (but not exclusive) interest to the financial sector. The focus is on the following programs:

  • The securities-focused “Chinese Military Companies Sanctions” program
  • The four Russia-related “sectoral sanctions” directives (e.g., “new debt” and “new equity”)
  • The Russia-related “directives” imposing prohibitions on certain dealings in sovereign debt
  • The irregular Venezuela-related prohibitions on Venezuelan government debt and equity (and related general licenses)

In the second part of the class, we discuss methodologies for, and questions related to, the addressing of ambiguous provisions. This lesson has broad applicability to all OFAC-related primary sanctions questions, and includes the following:

  • Past and Parallel Practice: whether and under what circumstances it is advisable to presume that a standard provision will be interpreted harmoniously cross-programmatically
  • The Use and Significance of On-Website Guidance: a discussion of the role of FAQs, “Interpretive Rulings,” “FAQs,” enforcement actions and other documents published and current on OFACs website that do not technically have the “force of law”
  • The Use and Significance of Off-Website Guidance: a discussion of the role of published guidance removed from OFAC’s website, unpublished binding guidance letters, specific licenses, court filings and other “authoritative” interpretations of the law attributable to OFAC
  • Considerations for Approaching OFAC: calling the “hotline,” requesting formal guidance, or neither
Virtual Class 4: “Secondary Sanctions” and Other Provisions Targeting Conduct With No U.S. Nexus; Primary Sanctions in the Context of Non-sanctioned Territories Controlled by Sanctioned Entities (2 hours)
In the first part of this class, we address the application of the basic blocking prohibition (typically that of the Global Terrorism Sanctions Regulations) in the context of non-sanctioned countries or territories substantially controlled by blocked entities, all of which are subject to secondary sanctions in addition to primary sanctions prohibitions. These include Afghanistan (the Taliban); Gaza (Hamas) and parts of Somalia (al-Shabab).

We also address the important legal distinctions between primary and secondary sanctions regimes. These include the distinction between “prohibited” and “sanctionable” conduct, as well as the difference between the “licensing” and “non-enforcement” methods for mitigating the unwanted effects of the breadth of sanctions provisions.

This second part focuses on U.S. sanctions provisions that can trigger the “sanctioning” of non-U.S. persons for activities that may not—and typically does not—have any nexus to the U.S.

We provide an overview of the active authorities and sets out an analytical framework for addressing “secondary sanctions” problems:

  • Question 1: Is the transaction within the theoretical scope of a secondary sanctions or “derivative designation” provision?
    • What is the meaning of the term “significant transaction”
    • What is the meaning of the term “materially assists”
    • What does it mean to “operate in” a targeted sector of a given economy?
  • Question 2: Does a statutory exemption or exclusion to the sanctions provision apply?
  • Question 3: Would the transaction require a specific license if engaged in by a U.S. person?
  • Question 4: How do we assess the risk that a theoretically sanctionable transaction carries a material designation risk?
  • Question 5: Is it possible to seek comfort from OFAC or the State Department that theoretically sanctionable conduct will not result in the imposition of sanctions?
End Exam (1 hour)
The exam consists of a short series of multiple-choice questions and a case study that calls for a written, one-page answer. Learners will download the questions from the platform and upload their answers upon completion. The exam will be graded on a pass/fail basis, and the instructor will provide individualized feedback on the written response portion.

Estimated time investment: 1 hour


Brian Gatta

Brian is a Director and founder of Sanctions Inc., home of the TURBOFAC ( suite of post-screening sanctions solutions. Brian’s principal focus is on the maintenance and advancement of the TURBOFAC U.S. Sanctions Guided Interview System and the TURBOFAC Comprehensive U.S. Sanctions Research System and Encyclopedia. Brian’s work in creating and maintaining TURBOFAC entails the thorough review and annotation of every consequential statement attributable to OFAC, in addition to the transformation of the entirety of the OFAC-administered sanctions architecture into a single, multiple-choice “guided interview” program.

Prior to his work at Sanctions Inc., Brian spent over a decade as an attorney practicing in the international trade groups of large law firms. Brian graduated with honors from Columbia Law School in 2007.