WASHINGTON — When Major League Baseball completed a deal with the Cuban government last week to hold an exhibition game in Havana duringPresident Obama’s planned visit this month, White House officials quietly rejoiced that a pivotal piece of their plan had fallen into place after weeks of intensive negotiations.

It was just one aspect of an elaborate behind-the-scenes effort by American and Cuban officials to ensure that Mr. Obama’s historic visit to Cuba yields the powerful symbolism and concrete policy progress they are seeking.

Both sides have a lot at stake. A successful trip could vindicate the decisionby Mr. Obama and President Raúl Castro of Cuba to pursue an official thaw, broadcasting to both of their publics the possibilities of a new relationship and building political support in the United States for ending a decades-old trade embargo.

But a misstep or public dispute has the potential to set back that goal by highlighting the deep differences that remain between the United States and Cuba. There is also the risk of dissonance in trying to open a new chapter in relations when so many of the old plotlines, including differences over human rights violations by Mr. Castro’s government, are still playing out.