“We’ve been engaged in a failed policy with Cuba for the last fifty years, and we need to change it,” Barack Obama declared as a presidential candidate in 2007. Just last November, Obama reiterated to his Cuban-American supporters in Miami: “The notion that the same policies that we put in place in 1961 would somehow still be as effective…in the age of the Internet and Google and world travel doesn’t make sense.” For six years, President Obama has been saying that US policy toward Cuba needs to change, but for six years he’s been unwilling to take the political risk of sitting down at the negotiating table with the Cuban government to make it happen.

Despite rampant rumors in Washington that administration officials at the “highest levels” want to break the stalemate in relations, no major breakthroughs have occurred. If Obama really wants to revamp fifty years of failed policy, he’d better act soon, because time is running out.

To his credit, Obama’s policy of expanding connections between US and Cuban societies has been hugely successful. In 2009, he lifted virtually all restrictions on Cuban-American travel and remittances, leading to a rapid expansion of both. In January 2011, after the midterm congressional elections, he reopened educational travel for non-Cuban Americans, restoring the broad people-to-people travel category that President George W. Bush had abolished.

But when it comes to state-to-state relations, Obama’s Cuba policy has been much less forward-leaning. Washington’s dialogue with Havana has been limited to minor issues of mutual interest: Coast Guard search and rescue, oil-spill containment, restoration of direct postal service. Clearing the underbrush on such secondary matters could build confidence for talks on the central issues dividing the two countries, but thus far the political will to make that leap has been lacking.

Obama can’t dodge the Cuba issue much longer. The Seventh Summit of the Americas, scheduled for Panama next spring, will force Cuba to the top of the president’s diplomatic agenda. Washington blocked Cuban participation in the first six summits, on the grounds that the participants had to be democracies. At the last summit in Cartagena, Colombia, however, the Latin American heads of state warned Obama that there would be no seventh summit unless Cuba was included. Despite US objections, on September 18, Panamanian foreign minister Isabel Saint Malo traveled to Havana and issued a personal face-to-face invitation to President Raúl Castro.

Castro, who took over from his ailing brother Fidel in 2006, has already indicated that Cuba will attend. Obama now faces a decision: either participate in a summit that includes Cuba, or else boycott it and do enormous damage to US hemispheric relations. Early signals from inside the administration suggest that Obama will participate.

As the summit approaches, the real issue will be whether the administration treats Cuban participation as a domestic political problem to be finessed or as a diplomatic opportunity to break the bilateral stalemate. Conservatives in Congress and in Obama’s foreign-policy bureaucracy will push the president to confront Raúl Castro at the summit in a way designed to irritate bilateral relations rather than improve them. Obama should resist that pressure and use the multilateral context of the summit as an opportunity to launch a sustained dialogue with Cuba—to finally make the breakthrough in policy that he has been talking about for the past six years.

If Obama decides on the latter course, there are a number of lessons he can learn from his ten predecessors, all of whom had some experience talking with Cuba. The lessons outlined below are adapted from our new book, Back Channel to Cuba: The Hidden History of Negotiations Between Washington and Havana.

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