Five Iranian tankers likely carrying at least $45.5 million worth of gasoline and similar products are now sailing to Venezuela, part of a wider deal between the two U.S.-sanctioned nations amid heightened tensions between Tehran and Washington.

The tankers’ voyage come after Venezuela’s socialist leader Nicolás Maduro already turned to Iran for help in flying in chemicals needed at an aging refinery amid a gasoline shortage, a symptom of the wider economic and political chaos gripping Latin America’s one-time largest oil producer.

For Iran, the tankers represent a way to bring money into its cash-starved Shiite theocracy and put its own pressure on the U.S., which under President Donald Trump has pursued maximalist campaigns against both nations.

But the strategy invites the chance of a renewed confrontation between the Islamic Republic and America both in the Persian Gulf, which saw a series of escalating incidents often involving the oil industry last year, and wider afield.

“This is like a new one for everyone,” said Capt. Ranjith Raja, an analyst who tracks oil shipments by sea at the data firm Refinitiv, of the gasoline shipments. “We haven’t seen anything like this before.”

All the vessels involved belong to Iranian state-owned or state-linked companies, flying under the Iranian flag. Since a pressure campaign on Iranian vessels began, notably with the temporary seizure of an Iranian tanker last year by Gibraltar, the country’s ships have been unable to fly flags of convenience of other nations, a common practice in international shipping.

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