Cuba claims its healthcare system is struggling under US energy sanctions affecting children's health and daily life, even as US exports to Cuba have jumped dramatically in 2026 through businesses exploiting a trade loophole to send fuel, food, vehicles and other goods past Trump administration sanctions.
The Trump administration announced new economic sanctions targeting Cuban President Miguel Díaz-Canel, his wife, and members of the Castro family, marking the latest escalation in US pressure on Cuba's leadership amid ongoing food shortages and blackouts on the island.
General Francis Donovan, commander of U.S. Southern Command, met with senior Cuban military officials on Friday at the perimeter of Naval Station Guantanamo Bay in a rare high-level military engagement. The meeting focused on operational security matters and comes amid heightened tensions as the Trump administration increases pressure on Cuba.
Cuba released the names of thousands of prisoners covered by a previously announced amnesty as the government engages in tense negotiations with the United States over various disputes, including the issue of political prisoners.
The Supreme Court ruled in favor of allowing the Havana Docks Corporation to pursue compensation for property confiscated by Fidel Castro's regime in 1960, with the Trump administration backing the lawsuit against major cruise lines over use of Port of Havana docks.
Cuba's national electricity grid suffered multiple nationwide collapses in March 2026, leaving millions without power after the United States imposed an oil blockade on the island. President Donald Trump publicly mused about taking over Cuba as the crisis unfolded.
U.S. Secretary of State Marco Rubio delivered a message to the Cuban people offering a potential 'new relationship' with the United States while condemning the island's Communist leadership. The outreach was made in Spanish on May 20, 2026.
The Trump administration has indicted former Cuban President Raúl Castro on murder charges related to the 1996 downing of planes operated by Miami-based exile group Brothers to the Rescue. The indictment escalates Washington's pressure campaign seeking regime change in Cuba.
Classified intelligence reports indicate Cuba has purchased more than 300 military drones from Russia and Iran and discussed plans to potentially use them against US soil and Caribbean assets, raising concerns among US officials about hostile technologies in close proximity.
Cuba has rejected US military assessments alleging that the island nation acquired over 300 military drones and discussed plans to attack the US naval base at Guantanamo Bay, US vessels, and potentially Key West, Florida. Cuban Foreign Minister Bruno Rodriguez characterized the claims as fabrications.
CIA Director John Ratcliffe led a U.S. delegation to Havana on Thursday for talks with Cuban government officials, including Raul Castro's grandson, as Cuba faces a collapsing energy sector. The Trump administration indicated it will only engage if Cuba makes fundamental changes.
Cuba's energy minister announced the country has completely depleted its oil and diesel supplies amid a U.S. blockade that tightened after Venezuela stopped fuel shipments following its president's capture in January. The crisis has triggered rolling blackouts in Havana and protests in the capital.
President Trump is reportedly growing impatient with Cuba's government maintaining power despite months of U.S. pressure, prompting warnings from both Senate Republicans and over 30 members of Congress against military strikes or invasion. Lawmakers cite concerns about military overextension with Iran and the use of Guantánamo Bay for migrant detention.
The Trump administration imposed financial sanctions on Cuba's military-run business conglomerate GAESA and a Cuban-Canadian mining joint venture, prompting Toronto-based Sherritt to withdraw from its Cuban operations. Despite Trump's repeated threats that 'Cuba is next,' the US ruled out imminent military action.
China and Russia rallied behind Cuba's government amid mounting US pressure, as Moscow's deputy foreign minister concluded a Havana visit and Beijing signaled support, while Cuban President Díaz-Canel vowed to resist US demands for his resignation.
Cuba announced it will pardon 2,010 prisoners in what it calls a 'humanitarian gesture' during Holy Week, marking the second wave of releases in less than a month as the island faces mounting US pressure and an energy crisis under fuel blockade.
Treasury Secretary Scott Bessent announced the US will temporarily allow the sale of Iranian oil shipments already in transit, estimated to add 140 million barrels to the market. The move comes as oil prices hit their highest settlement since July 2022 amid Iran's closure of the Strait of Hormuz during the ongoing US-Israeli conflict with Iran.
Raúl Guillermo Rodríguez Castro, the influential grandson of former Cuban leader Raúl Castro, has become a central figure in ongoing diplomatic negotiations between the United States and Cuba, even as his grandfather faces a murder indictment in Miami related to a 1996 incident.
President Donald Trump has signed multiple executive orders threatening to impose tariffs on countries that continue to trade with Iran or provide oil to Cuba, escalating economic pressure on both nations and potentially affecting major trading partners like Mexico.
