U.S. and Cuban authorities will kick off historic meetings on Wednesday, delving into talks on migration and first steps in normalizing relations between the countries. If all goes well, the meetings could fast-track Washington, D.C., and Havana toward a new diplomatic relationship -- but much will depend on how much Cuba is willing to give.

Roberta Jacobson, U.S. assistant secretary of state for Western Hemisphere affairs, will meet with Cuban officials Jan. 21-24 in Havana. Wednesday’s meeting on migration will be an extension of bilateral migration talks that have been taking place roughly every six months since 1995, but Jacobson’s attendance will mark the highest-level U.S. delegation in more than 30 years. On Thursday, officials will start nuts-and-bolts discussions about reopening the U.S. embassy in Havana, including reaccrediting diplomats, allowing shipments to the embassy and ensuring Cubans have access to the facility.

Progress in U.S.-Cuban cooperation, however, will depend heavily on the Cuban government, a senior administration official said in a conference call with reporters Monday. The official, who asked not to be named, said Washington, D.C., was still keenly aware of the fundamental disagreements between the two administrations and that this week’s talks would provide further clues about how willing Cuba might be to work with U.S. officials in the coming months.

One of those disagreements concerns Cuba’s protection of U.S. fugitives on its soil, including Assata Shakur, also known as Joanne Chesimard, who was granted asylum in Cuba after being convicted in the U.S. of shooting a New Jersey state trooper in 1973. The extradition of Shakur has always been a topic of discussion during the migration talks, the official said, but Cuba has consistently refused to budge on the issue, despite cooperating on returning other U.S. fugitives. “They have taken the request [to extradite Shakur], and they have not really provided much rationale in response to a negative reply,” the official said.

Another part of the normalization process will be raising questions about settling U.S. claims for property seized by the Cuban government after the 1959 revolution. According to the U.S. Foreign Claims Settlement Commission, U.S. nationals had about $1.8 billion worth of certified claims against Cuba’s government for the expropriations, mostly of corporate assets. That figure is now valued at $7 billion with interest. The White House official acknowledged that sorting out those claims would be a “complicated” process that would take much longer than the more immediate tasks related to restoring the U.S. embassy.

While the migration talks have generally prioritized ensuring safe and orderly migration between Cuba and the U.S., the U.S.’ immigration policies won’t likely be a topic of conversation in this week’s meetings. The U.S. Coast Guard earlier this month reported a spike in Cuban migrants traveling to the U.S. by boat, which they attributed to fresh rumors that immigration privileges for Cubans would soon end. U.S. officials have consistently denied any forthcoming changes to the Cuban Adjustment Act, which grants Cuban immigrants a fast track to U.S. citizenship, saying only Congress could enact that type of change.

“The fact is there is no template per se,” the White House official said, referencing the process of normalization. “Diplomatic relations are restored by mutual consent of two governments.”

A high-level official with Cuba’s foreign ministry echoed that cautious sentiment during a separate briefing with reporters Tuesday. “Cuba is reestablishing diplomatic relations with the U.S.,” the official said. “The process of normalization is much longer and deeper.”

Despite the talks, some members of Congress are still looking to block the administration’s normalization efforts, either through defunding the embassy in Havana or blocking the confirmation of a new U.S. ambassador to Cuba. But congressional Republicans are divided over the issue, and it’s unclear how far those efforts will go.

Meanwhile, President Obama, speaking during the State of the Union address Tuesday night, took another opportunity to urge Congress to formally lift the embargo. "Our shift in Cuba policy has the potential to end a legacy of mistrust in our hemisphere; removes a phony excuse for restrictions in Cuba; stands up for democratic values; and extends the hand of friendship to the Cuban people," he said. "And this year, Congress should begin the work of ending the embargo."