US and Cuban officials have a laundry list of demands for their second round of diplomatic talks in Washington on Friday, aimed at burying a half-century of Cold War animosity.
Restoring diplomatic ties, a process that involves opening embassies, appears within grasp, but negotiators have indicated that normalizing other relations is a longer-term endeavor.
One month after they held a first set of talks in Havana, here are the main sticking points to resolve before the two nations can reestablish diplomatic ties and normalize relations.
Seeing the US and Cuban flags raised at embassies in their respective capitals would be a potent symbol of their bid to put their Cold War rivalry to rest.
The two nations severed diplomatic relations in 1961, two years after Fidel Castro led his guerrilla to victory over dictator Fulgencio Batista.
In 1977, US president Jimmy Carter and Fidel Castro agreed to open "interests sections" in each other's capitals, with limits on their operations and without ambassadors at the helm.
The goal now is to increase the number of accredited diplomats and lift limits on travel within each nation.
US and Cuban diplomats are not allowed to go out of Havana and Washington without official authorization from the host countries.
The number of diplomats was limited to 10 expatriates in 1977, though more were allowed over the years.
The two sides also aim to lift restrictions on diplomatic pouches. Havana has accused Washington of using them to import material used for "subversion," such as short-wave radios.
The United States demands that Cuba allow unimpeded access to its mission for Cubans. The seaside outpost is guarded by Cuban police who ask visitors to show identifications and explain the motive of their visit.
For its part, Cuba wants open access to banking services in the United States, a restriction that has severely curbed consular services. But Havana's main demand is more complex: The removal of Cuba from a blacklist of state sponsors of terrorism.
Normalizing relations is trickier and could take years.
Cuba's main gripe is the US embargo, which was fully implemented in 1962. Castro has demanded a "just compensation for our people for the human and economic damage that it has suffered" due to the trade sanctions.
Obama has asked Congress to lift the embargo, but his Republican rivals hold the majority in both chambers.
It is also up to the US Congress to satisfy Cuba's demand for Washington to end the Cuban Adjustment Act of 1966.
The law gives Cubans who set foot in the United States - legally or illegally - immediate access to residency and a work permit. Cuba says the act has encouraged an exodus from the island.
Cuban officials say Obama could use executive powers to bypass Congress and chip away at the embargo and the migration law.
In a January speech, Raul Castro said another hurdle was the US presence at Guantanamo Bay on the east of the island, where the US military has a naval base and a prison camp for terror suspects.
US officials say Obama has no plans to return the territory which has been in US hands for more than 100 years.
In another land feud, Cuba could be asked to compensate the United States for the nationalization of properties during the revolution, which Washington estimates at $7 billion, including interests.
Other demands include Cuba's desire to see an end to the US-funded anti-Castro radio and TV broadcasts.
The United States wants Havana to take back Cubans with criminal records who emigrated in the 1980s and must be deported. Havana has only accepted six of them from an estimated 25,000.