The Presidential Executive Order of 1 May 2026 marks a significant development in the United States’ sanctions policy towards Cuba. By introducing, for the first time within this framework, a genuine mechanism of secondary sanctions targeting foreign actors, Executive Order 14404 considerably expands the extraterritorial reach of the regime. Non-U.S. companies and financial institutions are now directly exposed to asset-freezing measures for activities connected to the Cuban economy, thereby increasing the legal and operational risks associated with any engagement with the island.

While compliance with international sanctions is a critical issue for companies, it is equally critical for executives. Indeed, since violating international sanctions constitutes a criminal offense, individuals may be prosecuted personally in the same way as legal entities. While the exclusively professional context does not allow individuals to avoid liability, delegations of authority may, under certain conditions, limit such liability.

The forthcoming adoption of the 20th package of sanctions against Russia raises questions not only about the legislative arsenal but also about the increasingly structured enforcement capabilities of national authorities. The broadened definition of circumvention requires companies to exercise greater rigour so they can consistently demonstrate that they have actively sought to avoid indirectly participating in a prohibited transaction.