What Is Going On Between Cuba and the United States?

CUBA · UNITED STATES · EXPLAINER

Washington is squeezing Cuba’s oil supplies, sanctioning its president and pursuing murder charges against its former leader, and this guide explains in plain English what is happening and what could come next.

Cuba-US tensions have hardened through 2026, as Washington squeezes the island’s oil supplies, sanctions President Miguel Díaz-Canel and pursues murder charges against former leader Raúl Castro over a 1996 shootdown. President Donald Trump says he expects a deal with Havana, while US military planners have studied options and Cuba’s government vows to resist any attack.

For Americans the stakes are close to home, from Florida’s large Cuban community to new limits on travel and the risk of a clash in the Florida Straits. Prediction markets still treat force as unlikely, pricing a US strike on Cuban soil by 31 December at 8.5% on Wednesday 21 October at 9:38 a.m. ET.

The Short Answer

The United States is using economic pressure, criminal cases and the threat of force to push Cuba’s communist government towards change. Trump told the UN General Assembly in September that the government “will fall”, according to CBS News, while saying Secretary of State Marco Rubio was “deep into negotiations” with Havana.

Díaz-Canel accuses Washington of “aggression” and “economic warfare”, and he has said he will not resign. Cuba’s ambassador to the UN said in April that the fate of detainees on the island is not on the negotiating table.

Nobody knows how the standoff ends, and the realistic paths range from a negotiated deal to a long squeeze, a sudden fall of the government in Havana or a US strike. Prediction markets give each dramatic outcome, a deal, the fall of the government or a strike, roughly a one-in-ten chance before the end of the year, which suggests traders expect the squeeze to drag on into 2027.

How the Squeeze Began

The turning point came on Saturday 3 January 2026, when US forces captured Venezuela’s leader Nicolás Maduro, a long-standing ally of Havana. A day later Rubio said Cuba’s government was “in a lot of trouble”, and on 11 January Trump urged Havana to make a deal “before it is too late”.

On 27 January Mexico’s President Claudia Sheinbaum said the state oil company Pemex had at least temporarily stopped shipments to Cuba, calling it a sovereign decision. Two days later Trump signed Executive Order 14380, which declared a national emergency over Cuba and allowed tariffs on goods from any country that sends oil to the island.

Trump ended the tariff threat on 20 February with Executive Order 14389, but the national emergency stayed in force and US agents have kept stopping Cuba-bound fuel. Cuba received its first fuel delivery in three months only on 31 March, when a sanctioned Russian tanker docked on the island.

The interceptions continue. On 7 October Homeland Security Investigations in Miami said it had seized more than 600,000 gallons of biodiesel, worth about US$2.8 million, bound for the Cuban state firm ENETEC.

Sanctions Aimed at Cuba’s Leaders and Money

The second front is financial. On 1 May Trump signed Executive Order 14404, which lets Washington punish anyone operating in Cuba’s energy, defence, mining, financial or security sectors and threatens foreign banks that handle “significant” transactions for blacklisted Cubans.

The Treasury has used it again and again. It added the new order’s tag to the existing listing of GAESA, the business group run by the armed forces, on 7 May, sanctioned Díaz-Canel, his wife Lis Cuesta and the armed forces ministry on 4 June, and blacklisted the tourism ministry on 13 July.

On 3 September it targeted the state bank Banco Exterior de Cuba and the fuel trader Comercial Cupet, and on 15 October, alongside a separate set of Iran-related sanctions, it blacklisted the Havana bank BICSA. A rule that took effect on 30 September also banned indirect payments to firms on the State Department’s Cuba Restricted List and ended “U-turn” transfers that let US banks process Cuba-linked payments between foreign parties.

Together the measures aim to cut Cuba’s state and military companies off from US dollars and from their foreign partners. Our explainer on who backs Havana and who presses it covers how Russia, China and Mexico have responded.

Why Raúl Castro Faces Murder Charges

On Saturday 24 February 1996 Cuban fighter jets shot down two small civilian planes flown by Brothers to the Rescue, a Miami exile group, killing four men. Three of them were US citizens, and the US Justice Department says the jets fired on the planes outside Cuban territory.

On 20 May 2026 the Justice Department unsealed an indictment in Miami charging Castro, then Cuba’s armed forces minister, and five others with conspiracy to kill US nationals, four counts of murder and two counts of destroying aircraft. “This passage of time does not erase murder,” said Jason Reding Quiñones, the US attorney for southern Florida.

Florida added its own case on Monday 19 October, when Attorney General James Uthmeier announced a state arrest warrant charging Castro with conspiracy to commit first-degree murder. Uthmeier conceded that the 95-year-old is “probably not looking to march himself into Miami”, but said travel to a country with a US extradition agreement could lead to his arrest.

Havana rejects the charges. Díaz-Canel called the Florida warrant a “pathetic Miami circus” with an electoral motive, and Foreign Minister Bruno Rodríguez called it another “sterile manoeuvre” by anti-Cuban politicians in South Florida.

Castro has not appeared in any US court and, like every defendant, is presumed innocent unless proven guilty. Our profile of who runs Cuba covers his role today and the Raúl Castro arrest warrant in more detail.

Will the US Attack Cuba?

No US strike or invasion has happened, and no order has been reported. CBS News reported on 25 September that the Army Reserve was checking which police, medical and engineering units it could hand to Southern Command, which runs US forces in Latin America and the Caribbean, within four months.

US officials told CBS the request was part of continued planning aimed at Cuba, and an earlier CBS report in July said planners had examined options including an air assault by the 101st Airborne Division. Officials stressed that no decision had been made, and CBS found no sign that any unit had received deployment orders.

Trump’s own words have swung both ways. In March he said “Taking Cuba in some form, yeah” and “Cuba’s going to be next”, but in late September he said he did not think the military would be needed.

“Cuba and us will make a deal.” President Donald Trump, September 2026

Lawmakers have not stopped him. On 28 April Senate Republicans rejected a Democratic war powers resolution aimed at ending the energy blockade unless Congress approved it, and Díaz-Canel has vowed that Cuba will fight back against any attack.

Talks, Offers and Prisoners

Washington and Havana have kept talking even as the pressure grew. Díaz-Canel confirmed on 13 March that the two governments had held talks, and on 10 April a State Department delegation in Havana met Raúl Guillermo Rodríguez Castro, a grandson of Raúl Castro who has met US officials several times this year.

CIA Director John Ratcliffe visited Havana on 14 May, and US officials said in May that they had offered tens of millions of dollars in humanitarian aid and two years of free Starlink internet access for Cubans. Cuba announced on 2 April that it would pardon 2,010 prisoners as a humanitarian gesture, although its UN ambassador later said the fate of detainees was not up for negotiation.

No deal has emerged. Polymarket traders gave a US-Cuba economic deal by 31 December an 11.5% chance on 21 October, and Kalshi, a rival platform regulated in the US, priced a Trump trade or economic deal with Cuba before 2027 at 13%.

What the Squeeze Means Inside Cuba

The squeeze is felt most in homes and hospitals. UN News reported in May that blackouts lasted as long as 20 hours in some areas and that more than 100,000 patients, including 11,000 children, were waiting for delayed operations.

In June the UN human rights office said infant mortality had doubled to 9.9 deaths per 1,000 births and that essential medicines were at about 30% of normal supply. UN rights chief Volker Türk said “children are dying because doctors lack access to essential medical supplies and medicines”.

Washington says its measures target a repressive government, and its rules still allow Americans to send money to relatives in Cuba. Havana blames what it calls the US blockade, and our report on daily life in Cuba under the embargo shows how families cope.

The dispute returns to the UN General Assembly in late October, when it votes on its yearly resolution calling for an end to the embargo. Last year the resolution passed by 165 votes to 7 with 12 abstentions, and the United States voted against it.

Fewer Ways for Cubans to Reach the United States

Leaving Cuba for the United States has also become much harder. The parole programme that let Cubans with US sponsors fly in legally was ended in March 2025, and the separate Cuban family reunification parole programme was terminated in December 2025, with most of its paroles expiring on 14 January 2026.

Since June 2025 a presidential proclamation has restricted the entry of Cuban nationals, and a December 2025 proclamation kept those limits in place. The Cuban Adjustment Act of 1966, which lets Cubans who were admitted or paroled and have spent a year in the US apply for a green card, remains law.

What Prediction Markets Say

Traders on Polymarket priced a US strike on Cuban soil by 31 December at 8.5% on 21 October at 9:38 a.m. ET, six points lower than a month earlier, on US$5.4 million of bets. They gave a US invasion in 2026 a 5.5% chance, the fall of Cuba’s communist government 9.5% and Raúl Castro ending the year in US custody 5.3%.

The card below refreshes every 20 minutes and shows how much money stands behind each price. A market is a bet, not an expert forecast, and prices can swing within minutes of a single headline.

What It Means for You

For American travellers, tourism in Cuba remains illegal under US law, and since 30 September group “people-to-people” tours and trips for professional meetings are no longer covered by a general licence. Visitors travelling under categories such as family visits or “support for the Cuban people” face power cuts and a Level 2 State Department advisory, and our guide explains whether Americans can still travel to Cuba.

For investors, Executive Order 14404 means any company with Cuban partners in energy, mining or finance risks US sanctions, foreign banks included. For Cuban families in the United States, remittances remain legal, but the legal routes for relatives to join them have narrowed sharply.

What Is Not Known

It is not known whether Trump will order force, how far the talks have gone, or how long Cuba’s government can absorb the blackouts and shortages. The health of Raúl Castro, now 95, is another unknown that could change the picture quickly.

Nor is it clear how many countries will change their vote at the UN, or whether Mexico, Russia or others will risk US sanctions to ship oil to Cuba. The answers will decide whether 2027 brings a deal, a change of government or more of the same squeeze.

For the full picture, follow our dossier on Cuba-US tensions, our explainer on why Cuba’s power grid keeps failing and the Latin America Power Map. Our Cuba news page carries every new report.

Frequently Asked Questions

What is happening between Cuba and the United States?

The United States is pressing Cuba’s communist government with an oil squeeze, sanctions on its leaders and criminal charges against former leader Raúl Castro. The two governments have held talks, but no deal has been announced.

Will the US attack Cuba?

No attack has happened and no order has been reported, although US planners have studied military options, according to CBS News. On 21 October prediction markets put a US strike on Cuban soil by 31 December at 8.5%.

Why was Raúl Castro charged?

A federal grand jury in Miami charged him over the 1996 downing of two Brothers to the Rescue planes, which killed four men, three of them US citizens. Florida added a state warrant on 19 October, and Castro is presumed innocent.

Can Americans travel to Cuba?

Yes, but not as tourists, because each trip must fit a category authorised by the US Treasury, such as family visits or support for the Cuban people. Group people-to-people tours stopped qualifying on 30 September 2026.

What sanctions has the US imposed on Cuba in 2026?

An executive order of 1 May allows sanctions on Cuba’s energy, mining, defence, financial and security sectors and on foreign banks. The Treasury has since targeted President Díaz-Canel, the military business group GAESA, the tourism ministry and several banks.

When does the UN vote on the US embargo?

The General Assembly holds its yearly vote in late October, and in 2025 it backed Cuba’s resolution by 165 votes to 7 with 12 abstentions. The resolution is not binding on the United States.

Sources: US Justice Department, Raúl Castro indictment (20 May 2026); White House, Executive Order 14380 (29 January 2026); Federal Register, Executive Order 14389 (20 February 2026); White House, Executive Order 14404 (1 May 2026); OFAC, 7 May 2026; OFAC, 4 June 2026; OFAC, 13 July 2026; OFAC, 3 September 2026; OFAC, 15 October 2026; Federal Register, Cuban Assets Control Regulations (30 September 2026); State Department, Cuba travel advisory; Federal Register, end of parole programmes (25 March 2025); Federal Register, end of family reunification parole (15 December 2025); Proclamation 10998 (16 December 2025); USCIS, Cuban Adjustment Act; UN News (15 May 2026); UN News (8 June 2026); UN News, 2025 embargo vote; CBS News (25 September 2026); PBS NewsHour timeline (20 May 2026); NBC Miami (19 October 2026); CBS Miami (19 October 2026); Infobae/EFE (19 October 2026); WLRN (7 October 2026); NPR (28 January 2026); NPR (2 April 2026); Polymarket and Kalshi market data (21 October 2026).

Editorial responsibility: Matthias Camenzind, Editor-in-Chief · Editorial standards · Report an error