President Barack Obama heads to Havana this weekend, the most compelling development yet in his long-running drive towards full normalization with Cuba. At stake in the President’s visit is a desire to show progress on the December 2014 decision to reestablish diplomatic relations and to cement the president’s legacy on Cuba. But a number of contentious issues remain unresolved. Among them are the fate of the decades-old trade embargo—which, despite Obama’s repeated pleas, Congress is unlikely to lift any time soon; compensation for Cuba’s confiscation and nationalization of American companies and properties in the early days of the revolution; the status of Cuban emigrants now leaving the island in droves via Central America, with thousands stuck at several border points; Internet connectivity and censorship, which Obama has identified as an objective of his policy turn; and a desire to operationalize new U.S. regulatory changes aimed at increasing commercial ties with the island.

But there’s no doubt that the most pressing question of the trip will be how Obama pushes the issue of human rights, and what the Cuban government is willing to tolerate on this front. The sudden cancellation of Secretary of State John Kerry’s advance trip to Cuba illustrates the magnitude of this challenge at a time when politically motivated arrests, detentions, beatings and harassment of opposition members have been dramatically on the rise since normalization.

According to the Havana-based Cuban Commission for Human Rights and National Reconciliation, there were more than 8,500 arrests in 2015—and another 2,500 since January 1. Freedom House continues to rate Cuba as one of the most restrictive nations in the world in terms of civil and political liberties. These are worrisome trends. Obama has said his trip is conditioned upon a substantive meeting with civil society representatives and members of the opposition. And there is no doubt that the Cuban-American community—particularly those most affected by Fidel Castro’s coming to power and his government’s ensuing repression—will be monitoring the fine details of these developments closely.

Given the gulf between Cuban and American officials on many of these matters, we are unlikely to see fundamental, lasting change during the remainder of Obama’s presidency. Therefore, come January 2017, Obama’s successor will need to consider the virtues of maintaining the present course.

The field of potential successors represents an array of views on Cuba policy, from a continuation of Obama’s approach, as endorsed by Democratic hopeful Hillary Clinton, to a possible reversal of existing policy, as discussed by Cuban-American Senator Ted Cruz. Regardless of who occupies the White House in 2017, there are certain lessons we can take from history.

First, we have traveled down this road before. Efforts to normalize relations during the Jimmy Carter and Bill Clinton presidencies came to naught, halted by Cuban belligerence, refugee crises, American politics, and the downing of two U.S. civilian planes that resulted in the death of U.S. citizens. While Obama has expanded upon the measures of his predecessors, it would come as no surprise if a similarly disruptive development should frustrate normalization once again.

Second, if full normalization is to advance, it will probably come unevenly and with continued hesitation from Cuba. A key moment will arrive in 2018, when Raul Castro has said he will step down as president. Cuba’s Communist Party congress, planned for April, may provide details on what comes next, but it’s highly unlikely to represent any substantive break with the past—and may even unveil a dynastic succession. Waiting in the wings are like-minded comrades who will almost certainly reaffirm Cuba’s revolutionary and ideological ideals. And in the context of Castro’s departure and the decline of Venezuelan subsidies, Cuban elites will be eager to secure a substitute benefactor as well as to solidify full U.S. acceptance—and thereby maintain the current structure of power, inclusive of its repressive apparatus.

Third, regardless of whether the next president endorses Obama’s approach, he or she would benefit from close consultation with the current administration. Research into presidential transitions shows that the reflex to discount the experience of an outgoing administration has worked to the nation’s detriment. President John F. Kennedy himself recognized this dynamic; as he remarked in a tape-recorded observation, better coordination with Eisenhower’s team might have spared him from disaster at the Bay of Pigs. Likewise, the incoming administration, irrespective of party or policy preference, would benefit from the current team’s knowledge about their Cuban counterparts—including the intentions of Cuban elites, the fault lines that developed among them, and policy nuances to be exploited—as well as from the broader history of U.S.-Cuban relations.

Fourth, normalizations themselves offer uncertain outcomes, and we should be under no illusion as to the likelihood of realizing our objectives. Within the recent past, the United States has pursued major normalization projects roughly twenty years apart: with China in the 1970s, with Vietnam in the 1990s, and now with Cuba in the 2010s. While American engagement has often generated reciprocal economic and geopolitical benefits, it has had little comparable impact on human and political rights; the events of Tiananmen Square and its aftermath, for instance, are only the most obvious examples of normalization and human rights running down parallel but clearly separate tracks. The cultural and historical ties that Washington shares with Havana are different and deeper than those it had with Beijing and Hanoi, and it is possible, however unlikely, that the pursuit of this particular normalization may portend a different result. At any rate, if those rights are not forthcoming, the virtues of pushing forward with normalization will appear all the more dubious.

Lastly, while the Cold War is over, the principles and values guiding U.S.-Cuban relations—and U.S. foreign relations more generally—transcend the Cold War, and Washington should remain firm in its adherence to them. At a time when a host of global frictions have chipped away at international norms and undermined the cause of human rights, Washington should signal its determination to uphold these principles, even as it charts a new course in a complex, often stormy, and emotionally charged relationship. The message delivered to allies, adversaries, and the international community alike would be well worth sending.

Cristina Lopez-Gottardi is an assistant professor and research director for Public and Policy Programs at the University of Virginia’s Miller Center. Marc J. Selverstone is associate professor and chair of the Presidential Recordings Program at the Miller Center.