On Thursday, US Secretary of State John Kerry sat down for talks with Cuban Foreign Minister Bruno Rodriguez in Panama City.
The US government said the meeting went well.
"Secretary Kerry and Cuban Foreign Minister Rodriguez had a lengthy and very constructive discussion this evening. The two agreed they made progress and that we would continue to work to resolve outstanding issues," a senior State Department official told Reuters.
The talks came on the eve of today’s Summit of the Americas in Panama, where both Cuba and the United States will be present for the first time ever, along with every other nation in the region.
Obama and Cuban President Raul Castro will cross paths, and are expected to at least shake hands. The two leaders spoke by phone Wednesday ahead of the historic summit. No details about the call were released.
Obama is expected to agree with the State Department’s recommendation to remove Cuba from the list of countries believed to sponsor terrorism, although it is unknown if he will announce his decision during the summit.
Cuba's place on the terror list has been a major roadblock to ending more than five decades of estrangement between the two countries. Reversing it would help ease some financial sanctions against the island and make it easier for US companies to do business there.
A US official said Kerry and Rodriguez sought to smooth the way for Cuba's removal from the list, Reuters reported. Havana has demanded its removal before diplomatic ties can be restored.
The United States has pushed for Cuban assurances of no future support for terrorism, and Cuba has responded by making the same demand of Washington.
Months later, on New Year’s Day 1959, US-backed dictator Fulgencio Batista fled the island as Fidel Castro and his revolutionaries seized control.
Since the revolution, the only other high-level meeting between US and Cuban officials took place in 1959, between then-Vice President Richard Nixon and Castro, who was Cuba's prime minister at the time.
Relations between the United States and Cuba rapidly deteriorated soon after, and the United States broke off diplomatic relations in 1961, also imposing a trade embargo that Cuba blames for many of its economic problems.
While Obama has already relaxed some trade and travel restrictions, only the Republican-controlled Congress can overturn the embargo, and the president faces fierce opposition from some lawmakers.