Twenty-four hours before coming face to face with Cuban President Raul Castro, President Obama on Thursday continued to extend an olive branch from Washington to Havana — but analysts say there are real questions about whether Mr. Castro truly is interested in friendly relations with the U.S.

At a town hall in Kingston, Jamaica — the president’s last stop before heading to the Summit of the Americas in Panama — Mr. Obama praised the “extraordinary” Cuban people and said it’s time for the two nations to put the Cold War behind them.

Also Thursday, the State Department completed its review of whether Cuba should be removed from the U.S. list of state sponsors of terrorism.

The State Department reportedly will recommend to the president that Cuba be taken off the list, though it’s unlikely that Mr. Obama will announce a final decision in the next several days.

The Castro regime has made removal from the terrorism-sponsor list a prerequisite for the opening of a U.S. embassy in Havana and other steps forward in the diplomatic process.

Mr. Castro also has made other demands that the U.S. surely won’t meet, such as reparations for economic damages caused by the U.S. embargo on Cuba and the immediate transfer of Guantanamo Bay to the Cuban government.

Those seemingly unrealistic requests have led many analysts to question whether Mr. Castro truly wants to mend fences with the U.S. or whether he has been forced to begin cooperating with Washington out of sheer economic necessity.

Still, Mr. Obama expressed nothing but optimism Thursday.

“It is my strong belief that if we engage, that offers the greatest prospect for escaping some of the constraints of the past,” the president said at the Jamaica town hall. “I think the Cuban people are extraordinary and have huge potential. And what’s encouraging is the overwhelming majority of Cubans are interested in ending the last vestige of the Cold War and moving forward.”

Mr. Obama announced the historic diplomatic reboot with Cuba in December, but formalizing relations has got off to a slow start.

Analysts say that’s largely because of Mr. Castro, who in his heart likely wants to maintain the status quo.

“By engaging Cuba, I think the president is calling Castro’s bluff. And that’s why we have seen, since December, Raul Castro trying to raise the price of engaging Cuba” with his demands, said Juan Carlos Hidalgo, a policy analyst on Latin America at the Cato Institute’s Center for Global Liberty and Prosperity. “He looks like he’s trying to make up excuses to keep the United States an enemy.”

A poor economy in the communist-run island has forced Mr. Castro to the table, some analysts say, and it’s unclear whether he is willing to make the kinds of social and political changes Mr. Obama seeks. The White House continues to demand that Havana stop imprisoning political dissidents and committing other human rights abuses.

The U.S. ultimately may find itself in a situation with formal diplomatic ties with Cuba but also with major human rights objections — somewhat similar to the U.S. relationship with China, said Shannon O’Neil, senior fellow for Latin America studies at the Council on Foreign Relations.

“There is going to be a very calculated and probably slow process on the Cuban side,” she said on a conference call Thursday. “One could imagine that you could maintain a more authoritarian government with open relations [with the U.S.] — China is the one many people look to.”

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