On December 17, 2014, U.S. President Barack Obama and Cuban President Raúl Castro announced the beginning of a process of normalizing relations between Cuba and the United States. The normalization agreement was secretly negotiated in preceding months, facilitated by Pope Francis and largely hosted by the Government of Canada. Meetings were held in both Canada and the Vatican City. The agreement would see the lifting of some U.S. travel restrictions, fewer restrictions on remittances, U.S. banks' access to the Cuban financial system, and the reopening of the U.S. embassy in Havana and the Cuban embassy in Washington, which both closed in 1961 after the breakup of diplomatic relations as a result of Cuba's close alliance with the USSR.
On April 14, 2015, the Obama administration announced that Cuba would be removed from the United States State Sponsors of Terrorism list. The House and Senate had 45 days from April 14, 2015 to review and possibly block this action, but this did not occur, and on May 29, 2015, the 45 days lapsed, therefore officially removing Cuba from the United States' list of state sponsors of terrorism. This marked a further departure by the United States from the Cold War conflict and its strain on Cuba–United States relations. On July 20, 2015, the Cuban and U.S. "interests sections" in Washington and Havana respectively were upgraded to embassies.
Alan Gross returns to the United States on December 17, 2014, aboard a U.S. government plane; Gross was released by the Cuban government in a prisoner swap. In May 2012, it was reported that the U.S. had declined a "spy swap" proposed by the Cuban government, wherein the remaining three of an original group of Cuban prisoners the U.S. had convicted of espionage known as the Cuban Five, in prison in the U.S. since the 1990s, would be returned to Cuba in exchange for USAID contractor Alan Gross. Gross had been imprisoned in Cuba for providing illegal cellphone chips of a type used by CIA agents, which are designed to evade detection, in addition to computer equipment, satellite phones, and internet access to Cuba's Jewish community.
Although the Cuban trade embargo can only be ended by the U.S. Congress, the Obama administration took executive action to ease some restrictions on travel to Cuba by U.S. citizens, as well as restrictions on the import and export of goods between each country. In his 2015 State of the Union Address to Congress, Obama called on lawmakers to lift the embargo against Cuba, a message he reiterated in 2016.
In February 2015, Conan O'Brien became the first American television personality to film in Cuba in more than half a century (If you don't count Michael Moore's Sicko in 2007 or Anthony Bourdain's No Reservations in 2011). In May 2015, the Minnesota Orchestra performed several concerts in Havana, the first professional U.S. orchestra to play in Cuba since 1999.
On January 28, 2015, while attending a meeting of Latin American leaders in San José, Costa Rica, President Raúl Castro asserted that the United States should return the Guantanamo Bay Naval Base and lift the embargo on Cuba if relations were to be considered fully normalized.
The White House responded the next day, saying that it had no intention to return the base. White House spokesman Josh Earnest indicated any such move is out of the question. "The President does believe that the prison at Guantánamo Bay should be closed down, but the naval base is not something that we wish to be closed." This issue has yet to be resolved.
"State sponsor of terrorism" designation
In addition to Cuba's concern over U.S. migration policy, the Cuban delegation assured the U.S. that normalization talks would not yield significant changes unless Cuba is removed from the U.S. State Department's list of state sponsors of terrorism. Cuba was one of four countries on the list, the other three being Iran, Sudan, and Syria. The U.S. government said that it had begun an intelligence review in order to evaluate whether Cuba can be removed from the list.
On April 14, 2015, President Obama informed the United States Congress that he had decided to lift the designation of Cuba as a state sponsor of terrorism because "the government of Cuba has not provided any support for international terrorism during the preceding six-month period," and it "has provided assurances that it will not support acts of international terrorism in the future." The U.S. Congress could have prevented the removal of Cuba's designation by passing legislation within 45 days. Congress did not act, and Cuba was officially removed from the list on May 29, 2015.
On January 21, 2015, the United States and Cuba began bilateral talks in Havana to discuss further normalization issues. The U.S. delegation led by U.S. Assistant Secretary of State Roberta S. Jacobson, and Josefina Vidal Ferreiro, Cuba's head of North American affairs, sat down for the first day of closed-door talks in the capital’s Convention Center. The talks reportedly centered around migration policy. In particular, Cuban representatives urged the U.S. to end its immigration privileges to Cuban refugees, also known as the Wet feet, dry feet policy, which allows any fleeing Cuban citizens U.S. residency and citizenship, as long as they are found on U.S. soil and not at sea. Reuters reported that civilian uncertainty about the status of U.S. immigration policy following the thaw was promoting a surge of emigrants fleeing Cuba for the U.S.
U.S. President Obama and Cuban President Castro at Estadio Latinoamericano during Obama's visit to Havana President Obama arrived in Cuba for a three-day visit on March 20, 2016. Obama headed a delegation of between 800 and 1,200, including businesspeople and congressional leaders who had helped in establishing the 2014 normalization deal. Obama was the first sitting U.S. president to visit Cuba since Calvin Coolidge in 1928. Obama said that he would only visit Cuba if he could meet with Cuban dissidents: "If I go on a visit, then part of the deal is that I get to talk to everybody. I’ve made it very clear in my conversations directly with President Raúl Castro that we would continue to reach out to those who want to broaden the scope for, you know, free expression inside of Cuba.