U.S.-Cuba Relations Explained

During his 2008 presidential campaign, Obama said isolating Cuba had failed to advance U.S. interests and that it was time to pursue diplomacy with the Castro regime. Several weeks after taking office, he eased restrictions on remittances and travel, allowing Cuban Americans to send unlimited money to Cuba and permitting U.S. citizens to visit the island for religious and educational purposes.

As Obama began softening U.S. policy, Cuba signaled an openness to reform under the new leadership of Fidel’s brother, Raúl. Facing an aging population, a heavy foreign debt load, and economic hardship amid the global downturn, Raúl Castro began liberalizing Cuba’s state-controlled economy in 2009. His reforms included decentralizing the agricultural sector, relaxing restrictions on small businesses, opening up real estate markets, allowing Cubans to travel abroad more freely, and expanding access to consumer goods. Cuba’s private sector swelled as a result, and the number of self-employed workers nearly tripled between 2009 and 2013.

Obama and Raúl Castro surprised the world in December 2014 by announcing their governments would restore full diplomatic ties and begin easing more than fifty years of bilateral tensions. “America chooses to cut loose the shackles of the past so as to reach for a better future—for the Cuban people, for the American people, for our entire hemisphere, and for the world,” Obama said in a White House statement. The historic moment marked the culmination of eighteen months of secret diplomacy brokered by Pope Francis, during which the parties agreed to an exchange of prisoners, including Cuban intelligence officers and an American contractor, among other concessions.

In the following years, the Obama administration further loosened restrictions on remittances, travel, trade, telecommunications, and financial services, while rescinding Cuba’s designation as a state sponsor of terrorism—a major obstacle to normalization. Both governments also reopened their respective embassies, a move that was met with widespread public support in both countries.

In early 2016, Obama took another significant step toward normalization by visiting Havana, the first trip to Cuba by a sitting U.S. president since Calvin Coolidge in 1928. In a keynote address broadcast live, with Raúl Castro sitting in the audience, Obama urged the Cuban government to continue its political and economic liberalization and the U.S. Congress to lift the trade embargo. Later that year, U.S. commercial airlines began offering service between the countries for the first time in more than fifty years.

Days before he left office in January 2017, Obama rescinded the Clinton-era “wet-foot, dry-foot policy” [PDF]. The policy had allowed Cuban migrants who reached U.S. soil without visas to stay and apply for permanent residency, while those intercepted at sea were generally returned home. The rescission, which the Cuban government welcomed, ended what some had considered to be preferential treatment for Cuban immigrants and allowed those who arrived in the United States without visas to be placed in expedited removal proceedings.

The death of Fidel Castro and the election of Trump in 2016 rekindled debates over U.S.-Cuba policy. While in office, Trump followed through on campaign pledges to reverse course on much of the Obama administration’s so-called Cuban thaw. His first year coincided with the public emergence of “Havana Syndrome”—unexplained symptoms including hearing loss and cognitive impairment initially reported by U.S. intelligence officers and diplomats stationed at the U.S. Embassy in Cuba. Then-Secretary of State Rex Tillerson asserted that U.S. diplomats were purposefully being targeted. However, the Cuban government denied involvement and urged the United States not to cut diplomatic ties.

Nevertheless, the Trump administration withdrew all nonessential personnel from the U.S. Embassy in Havana in September 2017 and issued a travel advisory discouraging Americans from traveling to Cuba. The following month, Trump said he “believe[s] Cuba’s responsible” for the mysterious health attacks and expelled fifteen Cuban diplomats from Washington, a decision Havana condemned as “hasty, inappropriate, and unthinking.” His administration later prohibited commerce with businesses controlled by or operating on behalf of the Cuban military, intelligence agencies, and security services. (In 2020, the U.S. National Academies of Sciences, Engineering, and Medicine found that directed, pulsed radio frequency energy was the most plausible explanation for the symptoms associated with Havana Syndrome.)

During his presidency, Trump increased travel and financial restrictions on Cuba. This included banning Americans from individually traveling to Cuba for educational and cultural exchanges, significantly curbing remittances, and restricting flights to Cuban cities other than Havana. In 2020, the administration barred U.S. travelers from staying at hundreds of establishments linked to the Cuban government or Communist Party. (Americans have long circumvented travel restrictions by entering Cuba through third countries like Mexico.)

The White House further targeted Cuba’s finances by allowing U.S. nationals to sue entities that traffic in or benefit from property confiscated by the Cuban regime—a provision of the Helms-Burton Act that past U.S. presidents had routinely waived. Canada and the European Union, both major foreign investors in Cuba, pledged to protect their companies by fighting the decision through the World Trade Organization.

The Trump administration also grew increasingly wary of Cuba’s close ties with the embattled socialist regime of Venezuela’s Nicolás Maduro. It sought to curb oil shipments from Venezuela to Cuba by sanctioning [PDF] shipping firms, vessels, and Cuba’s state-run oil company. It also banned Cuban and Venezuelan officials deemed responsible for or complicit in supporting Venezuela’s human rights abuses from entering the United States. As one of Trump’s final acts, his administration redesignated Cuba as a state sponsor of terrorism, reversing Obama’s 2015 decision.

As a candidate, Biden pledged to reverse Trump’s policies on Cuba, which he said did not advance human rights or democracy. After taking office, his administration launched a review of those measures, signaling openness to lifting remittance restrictions, and appointed a high-level official to oversee the State Department’s response to the unexplained injuries reported by U.S. diplomats in Cuba. (U.S. intelligence agencies concluded in 2023 that the injuries were not likely to be caused by a foreign adversary.) At the same time, Havana made some economic reforms, including easing restrictions on private businesses and unifying its dual currencies. In April 2021, President Miguel Díaz-Canel—who took office in 2018—replaced Raúl Castro as the first secretary of the Communist Party, ending decades of leadership by the Castro family.

However, prospects for rapprochement dimmed after Cuba’s largest protests in nearly three decades erupted in July 2021. Demonstrators cited worsening economic conditions—including power outages, food and medicine shortages, and spiking inflation—while analysts blamed a combination of U.S. sanctions, government mismanagement, and a pandemic-related collapse in tourism. The Cuban government responded by blaming foreign provocateurs, arresting protest organizers, and clamping down internet and social media access.

Biden called on the regime to respect Cubans’ rights to protest and imposed new sanctions on several officials, including high-level members of the national police. In May 2022, following its Cuba policy review, the White House announced a series of measures to ease restrictions on the island, including expanding U.S. flights into the country, reestablishing a family reunification program, and lifting the remittance cap for families.

But conditions on the island deteriorated, and in March 2024, hundreds of demonstrators again took to the streets to decry mass power outages and food shortages. Unlike in 2021, the government responded by ramping up electricity generation and distributing subsidized food rations, some of which China supplied. Havana also reiterated its accusations that Washington was stoking public dissent with the aim of overthrowing the communist-run government, which the White House denied.

Cuba’s economic crisis also fueled what experts said was the largest wave of emigration in the island’s modern history; more than one million people (with some estimates as high as two million) had left the country since 2021, when the Castro regime ramped up repressive measures. To manage irregular migration to the United States, the Biden administration announced in January 2023 that up to thirty thousand Cubans would be permitted to enter the country each month under a humanitarian parole program. However, that April, the administration restarted deportation flights to Cuba after a two-year pause.

Like Obama, Biden attempted to soften U.S. policy toward Cuba during his last weeks in office, starting the process of removing Cuba’s designation as a state sponsor of terrorism and revoking a Trump-era memorandum that restricted U.S. tourism.

A year into his second term, Trump signed an executive order declaring that Cuba “constitutes an unusual and extraordinary threat” to U.S. national security, citing its ties to hostile actors like Russia. It also authorized tariffs on goods from third countries that sell or provide oil to the island—a move Cuban leaders warned would further strain the country’s economy. The order came weeks after the Trump administration announced it would take control of Venezuelan oil sales and stop shipments following the U.S. military’s January capture of Venezuelan leader Maduro. Venezuela has historically been a major oil supplier to Cuba, and the change forced the Cuban government to enact emergency measures to address fuel shortages during what experts say is the island’s worst economic and energy crisis in decades. 

Trump’s executive order has also left Mexican President Claudia Sheinbaum in a diplomatic bind. Besides Venezuela, Mexico was one of the few countries supplying oil to Cuba, and Trump’s order strained Mexico’s alliance with the island. Sheinbaum criticized U.S. sanctions as “unfair” but suspended oil shipments to Cuba in February. She also warned that the tariffs could lead to a “far-reaching humanitarian crisis” in Cuba and sent two Navy ships with aid to the island in wake of Trump’s executive order. The Trump administration also said it was sending $6 million in humanitarian assistance as conditions on the island have deteriorated. 

Meanwhile, tourism to Cuba—which has fallen significantly in recent years—is expected to fall further. Trump has called Cuba “a failing nation,” suggesting it would soon collapse without Venezuelan support. Secretary of State Marco Rubio has said the United States “would love to see” regime change in the country. Although Cuba has expressed openness to “meaningful” dialogue and Díaz-Canel has said he’s prepared to negotiate with the United States without pre-conditions, the country has rejected any discussions involving changes to its government. Havana has also firmly rejected “being portrayed as a threat to the United States” and condemned “all forms and manifestations” of terrorism, while affirming its commitment to upholding regional and international security.

Cuba’s exodus has also continued into Trump’s second term, though the number of Cubans encountered by U.S. officials dropped significantly in FY 2025, to approximately 33,000 from more than 217,000 the previous year. This decrease coincides with the Trump administration’s aggressive expansion of immigration enforcement and deportations.

The Congressional Research Service provides an overview of U.S. policy toward Cuba, as well as new developments under the second Trump administration.

This timeline explores the history of U.S.-Cuba relations since Fidel Castro seized power in 1959.

For the Foreign Policy Research Institute, Lewis Regenstein explores the history behind the mysterious illness known as “Havana Syndrome.”

For Foreign Affairs, the University of Miami’s Michael J. Bustamante analyzes Cuba’s economic and political outlook beyond 2026.

In her 2009 book Cuba: What Everyone Needs to Know, writer and scholar Julia E. Sweig offers a guide to the island’s politics, its relationship with the United States, and its shifting role in the world.

CFR’s John B. Bellinger III explains the legalities and consequences of the Trump administration’s plan to send immigrants to the U.S. military detention center at Guantánamo Bay, Cuba.t