My Business Writing professor said you couldn’t, but I don’t know. I asked Gemini to produce a summarized version of the OFAC Enforcement Guidelines, and this is what I got back:

This document acts as the “Sentencing Guidelines” for violating U.S. economic sanctions (OFAC rules). If you or your company trade with a banned country, terrorist, or sanctioned entity, this guide dictates your punishment.

Here is the condensed version of how it works:

1. The Spectrum of Punishment

When you break the rules, the outcome ranges from a slap on the wrist to a major blow:

• No Action: They drop the case.
• Cautionary Letter: A formal warning (“Don’t do it again”).
• Finding of Violation: A permanent mark on your record, but no money is owed.
• Civil Monetary Penalty: You are fined cash.

2. The “Scorecard” for Fines

If they decide to fine you, they don’t pick a random number. They use a formula:

• Base Fine: They start with a standard amount based on the dollar value of the illegal transaction.
• Adjustments: They raise or lower that amount based on General Factors:
  • Fine Increases: If you did it on purpose (willful), were reckless, tried to hide it, or have a history of breaking rules.
  • Fine Decreases: If you cooperated, had a compliance program in place to stop it (but it failed), and took immediate steps to fix the error.

3. The “Golden Rule” (Voluntary Self-Disclosure)

This is the most critical part of the document. If you find your own mistake and tell the government about it before they catch you, your base penalty is automatically cut in half (50% off).

The Bottom Line:

OFAC treats honest mistakes much differently than reckless law-breaking. If you mess up: Confess early, cooperate fully, and fix the problem to minimize your penalty.

So, I thought some important detail was missing, so I modified the prompt a few times:

Summarize https://www.ecfr.gov/current/title-31/subtitle-B/chapter-V/part-501/appendix-Appendix%20A%20to%20Part%20501 in layperson-friendly terms. Include discussion of the penalty process, the General Factors which go into the calculation of the penalty, including any subcategories under each General Factor, and the Penalty Grid, which is based on egregiousness of the conduct and voluntary self-disclosure. Include the entire Applicable Schedule Amount table, and the current statutory maximum fines under TWEA, IEEPA, and the Kingping Act. Include a short introduction, and a short section of takeaways.

and got back the following:

Here is a summary of Appendix A to Part 501 of Title 31 (Economic Sanctions Enforcement Guidelines), broken down into layperson-friendly terms.

Introduction

This document is the official “rulebook” used by the Office of Foreign Assets Control (OFAC)—the agency that enforces U.S. sanctions (like those against Iran, Russia, or terrorist groups). It explains exactly how the government decides on the punishment when an individual or company violates these sanctions. It is designed to make penalties predictable, consistent, and transparent.

The Penalty Process

When OFAC suspects a violation, they follow a formal legal process. They do not simply send a bill; you have opportunities to explain yourself.

1. Investigation: OFAC gathers evidence, often by issuing a subpoena (a legal demand for documents) or by reviewing a voluntary self-disclosure you submitted.
2. Initial Determination: OFAC reviews the facts and chooses an outcome:
   • No Action: The case is dropped.
   • Cautionary Letter: A formal warning. No fine is issued, but you are told to fix your compliance mistakes.
   • Finding of Violation: A formal record that you broke the law, but without a monetary fine.
   • Civil Monetary Penalty: A cash fine.
3. Pre-Penalty Notice: If they choose to fine you, they send this notice first. It explains what you did wrong and the proposed fine amount.
4. Response: You usually have 30 days to reply. You can argue that you are innocent or admit the mistake and argue for a lower fine based on the “General Factors” (see below).
5. Final Penalty Notice: After reading your response, OFAC issues the final fine.
6. Settlement: At almost any stage, you can negotiate a settlement to resolve the case (usually for a lower amount) without going through the full legal fight.

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General Factors (The “Scorecard”)

OFAC uses these factors to judge how “bad” the violation was. These are the levers that raise or lower your penalty.

A. Willful or Reckless Violation of Law (Intent)

• Willfulness: Did you know it was illegal and do it anyway?
• Recklessness: Were you careless? Did you ignore red flags?
• Concealment: Did you try to hide the evidence?
• Pattern of Conduct: Was this a one-time accident or a habit?
• Management Involvement: Did senior managers know?

B. Awareness of Conduct (Knowledge)

• Actual Knowledge: Did you know the transaction was happening?
• Reason to Know: Should you have known? Was the info readily available?

C. Harm to Sanctions Program Objectives (Impact)

• Economic Benefit: Did money or goods actually reach the sanctioned target?
• Implications for U.S. Policy: Did your action embarrass the U.S. or help an enemy?
• License Eligibility: If you had just asked for permission first, would OFAC have said “yes”? (If so, the harm is lower).

D. Individual Characteristics

• Commercial Sophistication: Are you a large, global bank (held to a high standard) or a small local business?
• Size & Financial Condition: Can you afford the fine?
• Sanctions History: Have you been in trouble with OFAC in the last 5 years?

E. Compliance Program

• Did you have an internal system (software/rules) to prevent this?
• Was that system appropriate for your company’s size?

F. Remedial Response (Fixing It)

• Did you stop the violation immediately?
• Did you investigate yourself to find the root cause?
• Did you implement new controls to ensure it never happens again?

G. Cooperation with OFAC

• Voluntary Self-Disclosure: Did you turn yourself in? (This is the most critical factor).
• Responsiveness: Did you answer OFAC’s questions quickly and honestly?
• Tolling Agreements: Did you agree to extend the statute of limitations to give OFAC more time?

H. Timing: How long ago did this happen?

I. Other Enforcement: Did another agency (like a banking regulator) already fine you?

J. Future Compliance: Will a fine here serve as a good deterrent for others?

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The Penalty Grid

OFAC calculates the “Base Penalty” using a matrix based on two questions:

1. Was the conduct Egregious (severe/willful)?
2. Did you Voluntarily Self-Disclose (confess)?

Scenario	Definition	Base Penalty Calculation
1. Non-Egregious + Disclosed	You made a mistake and told OFAC yourself.	50% of the Transaction Value (Capped at $188,850 per violation).*
2. Non-Egregious + No Disclosure	You made a mistake, but OFAC caught you.	The “Applicable Schedule Amount” (See table below).
3. Egregious + Disclosed	You did it on purpose, but you confessed.	50% of the Statutory Maximum.
4. Egregious + No Disclosure	You did it on purpose and OFAC caught you.	The Statutory Maximum.

*Note: For very small violations in Scenario 1, the penalty is capped at much lower amounts based on the schedule.

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Applicable Schedule Amount Table

This table is used for Non-Egregious cases (mistakes) where you did not voluntarily disclose. The fine is based on the value of the illegal transaction.

Transaction Value	Applicable Schedule Amount (Base Penalty)
Less than $1,000	$1,000
$1,000 to $10,000	$10,000
$10,000 to $25,000	$25,000
$25,000 to $50,000	$50,000
$50,000 to $100,000	$100,000
$100,000 to $200,000	$200,000
$200,000 or more	The Statutory Maximum (See below)

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Current Statutory Maximum Fines (2025)

For “Egregious” cases (or high-value non-egregious cases), the penalty is the “Statutory Maximum.” These amounts are adjusted annually for inflation. As of January 15, 2025, the maximums per violation are:

• IEEPA (International Emergency Economic Powers Act): The greater of $377,700 or twice the value of the transaction. (This covers most sanctions programs like Iran, Russia, and Terrorism).
• TWEA (Trading With the Enemy Act): $111,308. (Primarily covers Cuba).
• Kingpin Act (Foreign Narcotics Kingpin Designation Act): $1,876,699.

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Takeaways

• Honesty Saves Money: Voluntarily self-disclosing a violation automatically cuts the base penalty calculation in half.
• Intent is Expensive: The difference between “Egregious” (reckless) and “Non-Egregious” (mistake) is massive—often the difference between a $10,000 fine and a multi-million dollar fine.
• Compliance is a Shield: Even if you fail, having a compliance program in place lowers your penalty under the “General Factors.”
• Cooperate: Hiding documents or delaying the investigation is considered “Concealment” and will dramatically increase your fine.

Depending on what level of detail you need for your role, you may be able to deal with the ultra-condensed version. But it’s a cautionary tale about asking AI tools to summarize without knowing the source material and knowing what you want to see come back. And I suspect the Goldilocks result is really a combination of the two responses… but that’s just me.

What do you think?