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A Russian cargo plane typically used to transfer military equipment landed at a military airfield in Havana Sunday night, echoing flight patterns seen ahead of the capture of Nicolás Maduro in Venezuela.
The U.S.-sanctioned Ilyushin Il-76, operated by Russian state-linked airline Aviacon Zitotrans, was tracked landing at San Antonio de los Baños Airfield, a Cuban military installation roughly 30 miles south of Havana, according to public flight data.
Flight-tracking records show the aircraft stopped in St. Petersburg and Sochi in Russia; Mauritania, Africa; and the Dominican Republic. Each landing would have required approval from host governments, offering a window into which countries are continuing to permit Russian military-linked aviation activity despite Western sanctions.
The same aircraft conducted flights to Venezuela, Nicaragua and Cuba in late October 2025, as tensions between Washington and Caracas escalated. That movement preceded U.S. military action in Venezuela that ultimately ended Maduro’s rule — a sequence U.S. officials and analysts have since pointed to as a warning indicator when evaluating similar Russian aviation activity in the region.
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A Russian military Ilyushin Il-76 landed in Cuba Sunday night. (Delil SOULEIMAN / AFP via Getty Images)
Now, Cuban President Miguel Díaz-Canel finds himself under mounting pressure from President Donald Trump, who has sharply intensified U.S. policy toward Havana in recent weeks.
On Thursday, Trump declared a national emergency related to Cuba, asserting that the Cuban government poses an “unusual and extraordinary threat” to U.S. national security and foreign policy interests. The administration also said it would impose penalties on any country that sells or supplies oil to Cuba without U.S. authorization.
Trump confirmed Sunday that the U.S. is engaged in direct talks with Cuban officials.
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“Cuba is a failing nation. It has been for a long time, but now it doesn’t have Venezuela to prop it up,” Trump told reporters at Mar-a-Lago, Florida. “So we’re talking to the people from Cuba, the highest people in Cuba, to see what happens. I think we’re going to make a deal with Cuba.”
Trump and Secretary of State Marco Rubio both have indicated support for political change in Havana, though the administration has not said whether it would pursue that objective through military action.
Cuba’s President Miguel Diaz-Canel finds himself in President Trump’s crosshairs. (Pablo Porciuncula/AFP via Getty Images)
The same Russian aircraft flew into Caracas before Venezuelan President Nicolás Maduro was captured by U.S. forces. (Federico Parra/AFP via Getty Images)
Russian military ties to Cuba have repeatedly triggered concern in Washington. While the Soviet Union’s footprint on the island receded after the Cold War, Moscow has steadily rebuilt defense and intelligence cooperation with Havana over the past decade. U.S. officials have warned that renewed Russian activity in Cuba could pose security risks close to the U.S. mainland.
The Il-76 is a heavy transport aircraft capable of carrying roughly 50 tons of cargo or up to 200 personnel, a capability that has drawn scrutiny given the operator’s history. Aviacon Zitotrans has been sanctioned by the United States, Canada and Ukraine for supporting Russia’s defense sector.
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“Aviacon Zitotrans has shipped military equipment such as rockets, warheads, and helicopter parts all over the world,” the U.S. Treasury Department said in January 2023, when it added the airline to its sanctions list.
It remains unclear what cargo the aircraft carried on its most recent flight. During earlier operations in Venezuela, Russian state media and a Russian lawmaker said the same aircraft delivered Pantsir-S1 short-range and Buk-M2E medium-range air defense systems to Caracas.
