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Recent settlements in civil enforcement proceedings brought by the Office of Foreign Assets Control (OFAC) suggest that cover-ups, not crimes, may invite the stiffest penalties. Frequently, companies that cooperate with OFAC investigations, admit wrongdoing and take remedial actions to prevent future violations escape the enforcement process with mild punishments. Indeed, even companies that eventually cooperate after some initial resistance fare well in OFAC’s administrative enforcement process and often avoid criminal penalties altogether — penalties that, aside from the reputational damage, carry much more severe consequences, including prison time for individuals and massive financial impact.