Guidance for the talks, issued by the U.S. State Department, said the meeting was “to work out details for a pilot project to provide direct mail service.”
Both sides ended their first encounter in Washington in June with statements characterizing the meeting as positive and constructive.
The proposal to be discussed on Monday concerns letter service, not packages or express mail, a source, with knowledge of the discussions said.
U.S. postal service executive director for international postal services, Lea Emerson, is heading up the U.S. delegation to the talks.
Direct mail service between the United States and Cuba has been suspended since 1963. Despite the ban, letters and other mail still flow between the United States and the island nation 90 miles away through other countries, such as Canada, Mexico and Panama.
Relations between the two countries have been frozen since soon after Cuba’s 1959 revolution led by Fidel Castro.
The United States has maintained economic sanctions on Cuba for more than half a century.
Monday’s talks are taking place amid a few small signs the Obama administration and President Raul Castro have not completely given up on some improvement in the two countries’ hostile standoff.
Former British ambassador to Cuba, Paul Webster Hare, who currently lectures on international relations at Boston University, said Cuba’s decision not to allow former U.S. intelligence analyst Edward Snowden to fly from Russia to Cuba on the way to exile in Latin America, was significant.
“The Cubans recognized that for any prospect of better relations they needed to avoid more long-term irritants,” he said.
“In Secretary of State John Kerry, Cuba should recognize someone who has previously expressed himself against maintaining a travel ban for non-Cuban Americans. So policy change might not be out of the question,” Hare said.
Obama restarted immigration and postal talks with Cuba in 2009, both suspended by the Bush administration in 2004.
The separate talks were also seen at the time as a sign of further thawing in U.S.-Cuba relations under Obama, who had earlier relaxed restrictions on remittances and travel to the island for Cuban Americans.
Both the postal talks and immigration talks were suspended again soon after the arrest in December 2009 of U.S. contractor Alan Gross, sentenced in 2011 to 15 years for his role in setting up an underground Internet network in the Communist-run country.
Cuba has hinted at a possible swap of Gross for four Cuban agents arrested 15 years ago and still being held in the United States on espionage convictions.
Cuba allowed a U.S. doctor to visit Gross in August, something it had refused to do in the past.
A significant improvement is U.S.-Cuba relations must include the release of Gross and the Cuban agents, according to some analysts, while others said progress on secondary issues could lead up to a more significant change.
“Their release may ultimately come from a process of improving relations between Cuba and the U.S., where both nations engage in a progressive tit for tat,” Carlos Saladrigas, a successful Cuban American businessman who advocates engagement with his homeland and heads an organization of like-minded peers, the Cuba Study Group, said.
“Politically it is easier to conceive of their release as a consequence of a process than as the trigger,” he said.