As Cuban American Support for the President Wavers, the Trump Administration Implements Changes to Cuba Sanctions Regime
Overview: The Trump administration’s rhetoric and policy toward Cuba have continued to escalate in recent weeks, while Republican support among Cuban American and Hispanic voters in South Florida shows signs of strain ahead of midterm elections. New OFAC rules implemented on September 30 further restrict financial transactions involving Cuba’s private sector, potentially making it more difficult for private businesses to serve as an economic alternative to the state. Regardless, many Cuban American voters continue to hope that the administration will ultimately force political change on the island, with some already developing plans to bring capital to Cuba and help rebuild and reshape its institutions and industries in the event of a political transition, even as the prospects for near-term change remain uncertain.
On September 29, the U.S. Department of the Treasury’s Office of Foreign Assets Control (OFAC) announced several changes to the U.S. sanctions regime on Cuba. CEDA just released an explainer on these regulations with expert input from Dr. William LeoGrande, Professor of Government at American University and a leading expert on U.S.-Cuba relations.
Legally, the September 30 changes fall into two categories: (1) new regulations implementing the May 1 executive order, which imposes secondary sanctions on foreign entities that engage with Cuban government-linked entities; and (2) amendments to the Cuban Assets Control Regulations (CACR) that prohibit “indirect” financial transactions with those on the Cuba restricted entities list, eliminate the general license for U-Turn transactions, and narrow several travel general licenses and licenses that allow Cuba’s private sector to access U.S. financial institutions.
In practice, these changes make it more difficult for money, goods, and people to move between the US and Cuba, hitting the Cuban private sector the hardest. Most of the individual CACR changes reinstate restrictions first imposed during President Trump’s first term and later relaxed under President Biden. However, the complexity and volatility of the U.S. sanctions regime have led to overcompliance and risk aversion, which has forced Cuban private sector actors to operate outside U.S. jurisdiction to process transactions and access capital. Thus, while these OFAC changes narrow the handful of formal channels that remained, they also, in practice, don’t significantly augment the difficulties the Cuban private sector was already facing. Rather, these latest changes will likely worsen overcompliance, further narrowing the channels available to Cuba’s private sector.
These changes come months after Cuba’s government announced 176 economic reforms, some of which aimed to open the Cuban private sector. Oniel Díaz Castellanos, founder of Havana-based private consulting firm Auge, wrote on Facebook that these OFAC changes create obstacles for Cuban entrepreneurs to take advantage of the reforms by closing the door to nearly any opportunity for banking with the US and making it difficult for Cuban Americans to participate through seed capital or purchasing power.
The Trump administration and Cuba’s government have offered different rationales for the goals and impact of these changes. The State Department’s Assistant Secretary of State for Western Hemisphere Affairs stated that the measures were intended to close loopholes that Cuban authorities had used to evade sanctions and fund “Cuba’s repressive security apparatus.” Cuba’s President Miguel Díaz-Canel claimed that targeting the private sector effectively means targeting ordinary Cubans, calling the measures an attempt to inflict suffering on the Cuban people.
While the changes themselves are relatively narrow in scope, they come as part of a broader pattern of increasingly escalatory rhetoric and policy toward Cuba from the Trump administration. POLITICO reported that these measures may be aimed, at least in part, at appealing to Cuban American communities in South Florida, a historically important Republican constituency whose support for President Trump has reportedly weakened amid increased Immigration and Customs Enforcement (ICE) arrests and growing deportations of Cubans. An April poll found that 68 percent of surveyed Cuban Americans in South Florida disapproved of the administration’s push to deport Cubans without criminal records. Those sentiments have continued over the last few months as a September poll found that three in five Hispanic voters in Florida disapproved of President Trump’s job performance. Republican candidates have also responded to these tensions, with Representative María Elvira Salazar (FL-27) publicly rebuking the administration’s harsh enforcement policies.
However, the administration’s increasingly forceful rhetoric toward Cuba has fueled expectations that change on the island could be approaching. The Cuban American community in South Florida is preparing for a potential political transition, with regime change remaining a long-term objective for many (79 percent according to the Miami Herald), including Cuban American Secretary of State Marco Rubio. Since the beginning of the year, the Trump administration has repeatedly asserted “Cuba is next,” prompting some Cuban Americans to begin planning for a potential transition, including discussions around seed capital, infrastructure overhauls, and private business deals. The Wall Street Journal documented the extent of this planning and reported that Secretary Rubio has instructed his staff to continue regular Cuba-related announcements to maintain momentum even as the timeline for potential political change remains uncertain. One Department of State (DOS) official described the frequent announcements escalating policy toward Cuba as intended to “create the impression that further U.S. action could be imminent.”
Yet these expectations for political and economic openings are not manifesting in the way Cuban Americans have anticipated. The administration has taken a business-first approach to Cuba, with allies pursuing joint ventures involving Cuba’s industrial base and taking advantage of policy changes that are forcing some shipments to be routed through the US to avoid sanctions. The flip-flopping economic policies combined with the lack of movement on a political transition has reportedly unsettled Cuban Americans who expected political change, not commercial deals, to come first. That tension was underscored when President Trump told reporters last week that “I would say that Cuba and us will make a deal. I don't think we'll need the military.” Cuban officials have stated they welcome increased U.S. investment, but have denied that any formal talks with the administration are currently underway. Separately, reporting indicates that the administration is taking steps to prepare for potential military action should it ultimately choose that path.
All of this—the sanctions, the deal-making rhetoric, the domestic political calculus—remains far removed from the reality facing those on the ground in Cuba as blackouts, resource insecurity, and public health crises continue to worsen. A new report from the Cuban Observatory for Citizen Auditing (OCAC) found that the number of deaths relative to reported crimes nearly doubled between the first half of 2025 and the first half of 2026. A separate report from the United Nations Office for the Coordination of Humanitarian Affairs (OCHA) also found that roughly 75 percent of essential medicines are in short supply. Access to water has also deteriorated, with shortages now affecting an estimated 3.5 million people, up from 2.1 million in April. Whatever the sanctions are meant to signal in Washington or Miami, they are having minimal impact in improving the humanitarian, political, and economic situation for Cubans on the island. Read the explainer.
U.S.-CUBA NEWS
Trump’s UNGA Address Escalates Tensions with Cuba’s Government
On September 22, Cuba’s delegation to the UN walked out of the UN General Assembly (UNGA) during President Donald Trump’s address as he called Cuba “an absolutely failed state,” and said his administration was seeking “a fundamental change” on the island. Cuba’s Foreign Minister Bruno Rodríguez Parrilla responded to the address, rejecting President Trump’s remarks as falsehoods and defending Cuba’s sovereignty. President Miguel Díaz-Canel also rejected the portrayal of Cuba as a national security threat, accusing President Trump of using false claims to justify economic pressure and denying Cuban people’s right to self-determination.
President Trump later that week toned down his forceful rhetoric, telling reporters at the White House, “I would say that Cuba and us will make a deal. I don't think we'll need the military.” In his own UNGA address on September 26, Cuba’s Foreign Minister Bruno Rodríguez Parrilla said he hoped U.S. military intervention would never occur, and reaffirmed Cuba’s willingness to engage in bilateral conversations on the basis of sovereign equality, without interference in its internal affairs or preconditions.
According to an internal document obtained by the Associated Press, the DOS is considering additional restrictions on Cuban officials seeking to return to New York in October for the UN’s annual vote on a nonbinding resolution calling for an end to the U.S. embargo on Cuba. The proposed restrictions would make it impossible for Cuba to participate in a vote directly concerning U.S. policy toward the island, even as U.S. officials publicly discuss a possible agreement. In 2025, the resolution passed with 165 votes in favor, seven against, and 12 abstentions, despite a U.S. diplomatic campaign to secure opposition.
White House Rescinds $567 Million for Refugee and Entrant Assistance
On September 25, the Trump administration proposed canceling $567.4 million from the Refugee and Entrant Assistance account, drawn from the $6.3 billion Congress appropriated to that account in FY2024. The account funds Office of Refugee Resettlement (ORR) programs within the Department of Health and Human Services (HHS), including care for unaccompanied migrant children and assistance for refugees, asylees, eligible Cuban and Haitian entrants, trafficking survivors, and other qualifying populations. Although the HHS-administered Cuban and Haitian Entrant Program (CHEP) is no longer active, eligible Cuban and Haitian entrants can still receive assistance through ORR.
The request is part of an $810 million cancellation package submitted just days before the fiscal year ends on September 30. Congress normally has 45 days to consider a proposed rescission, during which the administration can withhold the funds. However, because these funds expire only five days after the request was submitted, these funds expired before Congress could complete its review, effectively allowing the administration to prevent them from being disbursed. The administration’s decision to withhold the requested funds until their September 30 expiration uses a “pocket rescission” approach that the Government Accountability Office (GAO) concluded in 2018 is not permitted under the Impoundment Control Act.
U.S. Container Shipments to Cuba Surge
Cargo vessels have made more than 200 trips from U.S. ports to Cuba this year, carrying food, solar panels, vehicles and other goods, according to Bloomberg. Together, those ships delivered nearly 720 million pounds of merchandise from ports including Miami, Houston, New Orleans, Jacksonville, and Wilmington by the end of August. One ship noted its average Cuba-bound cargo load has doubled compared with earlier in 2026. U.S. field and oil exports totaled $156.9 million during the first seven months of 2026, while U.S. agricultural and food exports to the island fell 11 percent over those seven months compared with January-July 2025.
While shipments from U.S. ports have increased, cargo from other countries still faces shipping disruptions. After the May 1 executive order expanded U.S. sanctions, Hapag-Lloyd and CMA CGM suspended bookings to and from Cuba. CMA CGM has since resumed limited service, but Cuba’s government says 7,000 containers from other countries remain stranded at ports in Jamaica, Panama, and Colombia. Some of that cargo is now being routed through U.S. ports to reach Cuba, giving U.S. shipping companies a larger role in delivering goods from other countries.
U.S. Coast Guard Intercepts Vessel Carrying Fuel Reportedly Bound for Cuba
On September 5, the U.S. Coast Guard intercepted a 300-foot cargo vessel carrying fuel reportedly bound for Cuba via the Caribbean Sea. A Coast Guard team boarded the ship and escorted it to Progreso, Mexico, where Mexican Navy inspectors found large quantities of fuel stowed in its ballast tanks. The New York Times reported on October 2 that the Coast Guard suspected the vessel of using “dark fleet” tactics such as switching off or manipulating tracking signals and using false shipping documents to conceal a vessel’s movement or cargo. Officials said intelligence indicated the fuel was destined for Cuba but did not disclose supporting details. The amount of fuel on board was unclear. The Coast Guard also disclosed an earlier seizure over the summer of another vessel carrying 210,000 gallons of fuel reportedly bound for Cuba. Both vessels’ last port of call was Colón, Panama, though officials did not identify the fuel’s origin or who arranged the shipments.
The interceptions mark a shift in how the administration enforces its de facto oil embargo. Until now, Washington had cut off Cuba's fuel supply largely through economic pressure: first tariff threats, which led Mexico to halt shipments in January, and then, after the Supreme Court struck down that tariff authority, the secondary sanctions authorized by the May 1 executive order. It also sharpens the administration's effort to close Cuba's economic "escape valves" while widening the channels it controls. As third-country shipments are stopped at sea, U.S. fuel sales to Cuba's private sector are surging: Energy Information Administration data show declared U.S. petroleum exports to Cuba rising from near zero in January to 26,000 barrels per day in June and 104,000 in July. Those sales are restricted to private buyers and do not supply the state-run power system, which suffered its seventh nationwide collapse of the year on September 18. Cuba produces only about 40 percent of the fuel it needs. The Trump administration's de facto oil embargo is causing fuel shortages affecting hospitals, water distribution, and transportation, and these new interceptions indicate fuel demands are unlikely to be addressed anytime soon.
GAO Finds Costly Errors in Guantánamo Detention Expansion
On September 24, the GAO released a report, requested by Senators Dick Durbin (IL), Jack Reed (RI), and Gary Peters (MI), finding that Immigration and Customs Enforcement (ICE) launched six detention expansion initiatives without a comprehensive plan, including one at Guantánamo Bay. In January 2025, President Trump announced plans to expand the detention facility on the island to hold up to 30,000 migrants. Military flights began transferring detainees in February 2025.
DHS had committed approximately $68 million to immigration detention at Guantánamo Bay through May 2026, and ICE had committed approximately $43 million through June, about $111 million combined. As part of the proposed expansion, the Department of Defense (DoD) spent $2.85 million to assemble tents for 5,000 people. DHS determined the tents did not meet detention standards and they were taken down without housing anyone. DoD officials told GAO the operation was downsized in mid-February 2025, weeks after it began, in part because building facilities that met ICE standards would cost too much. Rather than funding the original plan for new capacities, that money supported operations at two existing facilities on the base, which held an average of 16 immigration detainees per day in FY2026, far below the agency’s initial plan. GAO concluded that changing plans and high operating costs resulted in waste, but the unused tents are the only expense it specifically identified as wasteful.
By the end of August 2026, more than 800 migrants had passed through the naval base since the beginning of 2026, and DHS continues to use the base, where eight Somali migrants were being held as of mid-September.
Cuban Man’s Year in ICE Detention Raises Questions About Deportation Timeline
Antonio Frómeta Ascón has remained in ICE custody since August 14, 2025, in a legal limbo as Cuba declined to receive him during an attempted deportation in November. With the U.S. government acknowledging in a July court filing that his deportation timeline was “currently unknown,” he is seeking release under the Supreme Court’s Zadvydas v. Davis ruling. The ruling established six months as a presumptively reasonable period of detention after a removal order; beyond that period, a detainee may seek release by showing there is no significant likelihood of removal in the reasonably foreseeable future. Frómeta Ascón is now held at the El Paso Service Processing Center. The government acknowledges that it has no timeline for removal, an assessment that will be central to the court’s decision on his detention.
Before his transfer, Frómeta Ascón was held at Camp East Montana where he witnessed guards assault fellow Cuban detainee Geraldo Lunas Campos, who died in January. The El Paso County medical examiner ruled his death a homicide caused by asphyxia.
IN CUBA
Haitian Migrants Arrive on Cuba’s Southern Coast
On September 21, a makeshift boat carrying 17 Haitian migrants landed in Santiago de Cuba after a week at sea. The group of 14 men, one woman, and two children were allegedly attempting to reach the US before weather diverted them toward Cuba. A local Cuban Red Cross official said medical personnel examined the passengers and found no signs of an immediate health emergency, while immigration officials began identifying them. Their arrival comes as gang violence in Haiti has displaced nearly 1.5 million people, while insecurity disrupts livelihoods and access to humanitarian assistance.
Haitian boats bound for the US have reached Cuba before, including one carrying 842 migrants that landed in Villa Clara in 2022. Haitian arrivals are generally repatriated by air in coordination with the International Organization for Migration (IOM). IOM’s involvement with this group has not been documented, and no onward procedure has yet been announced, limiting information on potential returns.
Cuban Court Sentences Anna Bensi and Her Mother to Two Years of Restricted Liberty
On October 1, the People’s Municipal Court of East Havana sentenced Cuban content creator Anna Sofía Benítez Silvente, known as Anna Bensi, and her mother Caridad Silvente to two years of restricted liberty each. The women were convicted of “acts against personal and family privacy” under Article 393 of Cuba’s Penal Code after filming and posting a plainclothes police officer delivering a State Security summons in March. The women will serve their sentences outside prison under judicial supervision, and they are awaiting the written judgment specifying the sentences’ terms.
Bensi, 21, has gained an audience through videos criticizing Cuba’s government and restrictions on freedom. Cubalex legal advisor Raudiel Peña Barrios challenged the basis of the prosecution, arguing that recording officials performing public duties is a legitimate exercise of citizens' rights. According to the Miami Herald, access to the trial was restricted. Police detained evangelical pastor Rolando Pérez Lora as he attempted to accompany the women, and journalists Yoani Sánchez and Camila Acosta said authorities prevented them from leaving their homes to cover the proceedings.
Four of Cuba’s major registered Protestant denominations issued statements supporting Bensi and her mother. Multiple Cuban American members of Congress also condemned the prosecution. The case reflects continued restrictions on freedom of expression in Cuba, including the use of privacy charges against people documenting official conduct.
CUBA'S FOREIGN RELATIONS
Uruguay Proposes Payment Changes to Doctors Program Amid U.S. Pressure
Uruguay will maintain its medical cooperation agreement with Cuba while developing a mechanism to pay Cuban health professionals directly. The program supports eye care at the José Martí Specialized Eye Hospital in Montevideo and includes 21 Cuban health workers. Uruguay’s Secretary of the Presidency Alejandro Sánchez defended its continuation, citing its significant contribution to restoring patients’ sight.
The proposed payment changes follow Uruguay's inclusion among 15 countries identified by DOS as paying Cuba’s government for medical missions. Countries identified for two consecutive years could lose U.S. international assistance and military support. Uruguay received U.S. military assistance earlier this year with the delivery of an armored recovery vehicle that completed a 14-unit donation designated for UN peacekeeping operations.
Washington characterizes Cuba’s medical missions as forced labor, while Cuba’s government maintains that the missions’ earnings support its domestic health system. Uruguay’s Foreign Minister Mario Lubetikin said Cuba and the US had accepted moving toward direct payments, although technical details remained unresolved. The arrangement would preserve the program while addressing Washington’s objections to the payment arrangement. However, Mr. Lubetkin cautioned that Uruguay could not control whether the program participants subsequently transferred their earnings to Cuba’s government later.
Cuban Temporary Residence Approvals Increase in Jamaica
Jamaica granted 601 temporary residence permits to Cubans in the 2025-2026 financial year, up from 421 the previous financial year based on immigration agency records obtained by The Jamaica Gleaner. Temporary residence allows a limited stay, with duration dependent on factors including employment, study, or family relationships. Refugee applications remained comparatively few, with three in 2025 and four in 2026. Residency approvals are increasing at the same time as immigration enforcement, with Jamaica deporting 12 Cubans in 2025, including 11 convicted of illegal entry and one of overstaying.
A Cuban-born Jamaican citizen told The Gleaner that some Cubans remain in Jamaica while awaiting opportunities to reach the US. Now settled in Kingston, she coordinates deliveries of medical supplies to her parents through other Cuban residents traveling to the island and is considering bringing her parents to Jamaica. In May, Jamaica’s health minister confirmed that 42 Cuban doctors had chosen to remain under individual contracts, with some seeking permanent residence. Alongside the increase in temporary residence approvals, these decisions give Jamaica a role beyond transit, with existing professional and family connections providing a basis for Cubans to stay.
New Shipment of Chinese-Donated Solar Systems Arrives in Cuba
On September 23, Cuba received 200 containers of solar photovoltaic systems donated by China for a project to supply 5,000 systems to homes and public facilities. Chinese Ambassador Hua Xin announced that the equipment would serve remote areas. The shipment follows earlier Chinese donations of systems for rural homes in Cuba and essential services including health facilities and childcare centers. China has also supported grid-connected generation in Cuba, including the El Algarrobo solar park inaugurated in Guantánamo on September 8. While El Algarrobo supplies the national grid during daylight hours, the donated equipment targets electricity access at individual homes and services. The systems include storage batteries, allowing recipients to use stored solar electricity after sunset.
China’s support extends from household systems to Cuba’s planned expansion of 92 solar parks with roughly 2,000 megawatts of capacity by 2028. This expansion can reduce reliance on fuel-based generation, but its ability to address nighttime shortages depends on sufficient storage and reliable grid infrastructure.
Recommended Reading, Listening & Viewing:
Read | EL PAÍS: Neither US intervention nor Communist stagnation: Harvard’s proposed plan for Cuba
Read | Miami Herald: Miami’s plans for Cuba’s ‘day after’ revisit thorny questions about money, reconciliation
Go | Cuban Heritage Collection: Voices of a Changing Cuba
Coral Gables FL | Wednesday, October 7 @ 6pm
Read | Associated Press: Cuba’s cherished ballet tradition endures through daily blackouts and shortages
Read | Reuters: Viruses run rampant across Havana as water, power fails
Read | AULA Blog: U.S. Cuba Policy: Might Makes Wrong
Read | Miami Herald: Smuggling boat with people from China, Ecuador, Cuba is stopped off Florida Keys
Read | Americas Quarterly: Cuba’s Debate Is Missing What Cubans Want
Read | Lawfare: Siege Warfare by Other Means: The U.S. Economic Measures Against Cuba
