Cuba Strategic Advisory Team

Navigating Cuba‑related matters requires more than technical legal knowledge – it demands an informed, strategic approach grounded in regulatory fluency, political awareness and practical experience. Holland & Knight's Cuba Strategic Advisory Team works collaboratively with clients to manage risk, identify opportunity and move forward with confidence in one of the most complex and sensitive regulatory environments affecting international business today.

Our lawyers advise U.S. and international clients on inbound and outbound matters involving Cuba, with a focus on delivering clear, actionable guidance tailored to your commercial objectives and risk tolerance. Notably, we have extensive experience assisting clients with economic sanctions, exports, licensing and compliance matters before the U.S. Department of the Treasury's Office of Foreign Assets Control (OFAC) and the U.S. Department of Commerce's Bureau of Industry and Security (BIS).

What distinguishes our approach is the combination of deep legal experience and cultural fluency. With a significant Cuban‑American presence at the firm – including more than 200 Spanish‑speaking attorneys and one of the largest Latin America practices in the industry, we are distinctly positioned to advise clients on both the legal and practical realities of doing business connected to Cuba.

A Trusted Partner with Deep Multijurisdictional and Industry Experience

For more than 30 years, Holland & Knight has represented U.S. and international clients conducting business throughout Latin America and the Caribbean, and for more than 20 years we have counseled clients on Cuba‑related sanctions and export regulations, litigation and transactional matters. This depth of experience allows us to anticipate challenges, respond quickly to policy changes and provide practical solutions aligned with your long‑term strategies.

Our lawyers work across practice groups, drawing on capabilities in international trade, financial services, litigation, corporate, cross-border transactions and public policy. Clients benefit from coordinated, full‑service representation that addresses not only regulatory compliance, but also the broader commercial, operational and reputational considerations that become relevant when Cuba or a Cuban national are involved, even indirectly.

Our team’s experience advising clients affected by Cuba‑related restrictions spans a wide range of industries – including financial services, airlines, shipping, hospitality, travel, trade, insurance, agriculture and pharmaceuticals.

With a cross‑border presence that includes offices in Miami, New York, Mexico City, Monterrey and Bogotá, our multilingual and multicultural teams approach Cuba‑related matters with deep sensitivity to the political context and the evolving relationships among the U.S., Cuba, Latin America and other key jurisdictions.

Guiding You Through a Rapidly Shifting Landscape

U.S. policy toward Cuba has seen a number of changes since the enactment of the U.S. embargo and the Cuban Liberty and Democratic Solidarity (Libertad) Act of 1996, also known as the Helms-Burton Act. (See timeline of recent key changes below.) The most recent of these occurred in January 2026, when the Trump Administration issued an executive order authorizing tariffs on goods from countries that sell or provide oil to Cuba. It is anticipated that the administration and U.S. Congress will adopt further measures to increase economic and diplomatic pressure on the Cuban government.

Cuba‑related transactions continue to carry heightened compliance and enforcement risk. Our team helps clients evaluate those risks and design strategies that are legally sound and commercially viable. We advise on licensing, diligence, compliance, structuring and documentation, and we regularly represent clients facing enforcement inquiries or threatened litigation.

Notably, our attorneys have extensive experience assisting U.S. and foreign clients both threatened with and defending against claims under Title III of the Helms-Burton Act. We also counsel clients on the implications of Cuba's designation as a State Sponsor of Terrorism, including the enhanced diligence expectations and risk controls applied by financial institutions and other intermediaries.

How We Support Clients

Our Cuba Strategic Advisory Team responds to client inquiries with advice that reflects both the U.S. and Cuban perspectives. We stay current on regulatory, economic and policy developments affecting U.S.-Cuba trade, travel, communications and financial transactions, enabling us to provide you with timely guidance as conditions change.

Holland & Knight has been ranked in Chambers Latin America for Cuba Corporate/Commercial: International Firms since 2019, reflecting our commitment to responsive, thorough counsel across matters of all sizes. Our Cuba Strategic Advisory Team has been praised for providing "prompt and thorough counsel regardless of the nature or magnitude of the issue," with clients reporting "we have complete trust in their services and capabilities" and adding that "the team is client-oriented and provides proactive, efficient responses."

Clients also benefit from our leadership and involvement in organizations such as the Cuban American Bar Association, the Cuban‑American Caucus of State Legislators, the Cuban American National Foundation and the Florida Governor's Cuba Commission, as well as the Florida International Bankers Association's Sanctions Subcommittee. This engagement gives us insight into emerging trends and policy discussions that may affect our clients' interests.

A Proactive, Long‑Term Strategy

Changing policy creates both uncertainty and opportunity. Our team helps clients analyze developments, plan strategically and position themselves for future growth while managing legal and reputational risk. Clients across the U.S., Latin America and Europe rely on our attorneys not only for technical advice on Cuba matters, but for collaboration, cross‑practice coordination and a global perspective that supports informed, proactive decision‑making in one of the world's most challenging markets.

U.S. Policy Toward Cuba: A Timeline

March 1996: Helms‑Burton Act Enacted
The Cuban Liberty and Democratic Solidarity (Libertad) Act of 1996, also known as the Helms-Burton Act, established the statutory framework for the U.S. embargo and introduced Title III, authorizing claims related to confiscated property.

December 2014: Major Policy Shift Announced
The U.S. announced a change in policy toward Cuba, initiating a period of several years of expanded engagement and regulatory easing.

January-October 2016: OFAC Regulatory Amendments
OFAC amended the Cuban Assets Control Regulations (CACR) to significantly relax certain economic and trade sanctions, expand authorized travel, and increase the flow of information and commerce. On January 27, 2016, BIS amended the Export Administration Regulations (EAR) to expand License Exception Support for the Cuban People (SCP) and establish a general policy of approval for key categories of exports and reexports, such as certain telecommunications items, commodities and software, agricultural items, and items supporting civil aviation safety. It also adopted a case-by-case review policy for exports and reexports, including certain transactions involving state-owned enterprises and Cuban government agencies that provide goods and services intended to "meet the needs of the Cuban people." Still, the rule retained a general policy of denial for items benefiting revenue-generating state sectors (including tourism and extractive industries) and for end users associated with the Cuban military, police, intelligence or security services, as well as conditions on licenses to prevent reexports from Cuba to third countries.

November 2017: Sanctions Tightened
Further CACR amendments limited travel authorizations and restricted direct financial transactions with entities linked to the Cuban military (known as the Cuba restricted list). However, most of the earlier sanctions relaxations, regulated as general licenses under the CACR and the EAR, remained in place.

April-May 2019: Title III Fully Effective
One of the most significant changes in U.S. policy toward Cuba took place in April 2019, when the suspension of Title III of the HBA was officially lifted, and with it, the right to bring lawsuits against entities "trafficking" in confiscated property in Cuba became fully effective in May 2019.

January 2021: Cuba Redesignated as State Sponsor of Terrorism
Building on the shift toward renewed pressure on Cuba, the U.S. Department of State's redesignation increased compliance risk and diligence expectations for Cuba‑related transactions. The move reduced risk appetite for financing, remittances, and trade involving Cuba – even for activities authorized under OFAC's Cuba-related general licenses – because financial institutions and other intermediaries often apply enhanced risk controls to SST jurisdictions.

May 2024: New General Licenses Issued
The U.S. approved new general licenses aimed at expanding internet access, supporting U.S. digital services and encouraging independent private‑sector entrepreneurship in Cuba.

Early 2025: Policy Easing Announced, Then Reversed
Additional measures to ease sanctions were announced in January 2025 during the final days of the outgoing administration as part of a deal brokered by the Catholic Church with the Cuban government that included Cuba's promise to gradually release more than 550 political prisoners. However, those plans were soon reversed by the incoming administration.

January 2026: Executive Order on Cuba‑Related Oil Transactions
An executive order on January 29, 2026, authorized the imposition of tariffs on goods imported into the U.S. from countries supplying oil to Cuba. Although no amendments to OFAC or BIS regulations were announced at the time, the move signaled the potential for further economic pressure.