U.S. airlines Silver Airways and Frontier Airlines have become the latest to bow out of Cuba due to weakened demand, posing new questions about the U.S's future relationship with its former Cold War foe.
For a brief period under President Barack Obama, longstanding tensions appeared to be easing. But now, as the White House conducts a "full review" of U.S.-Cuba policies, diplomatic relations between the two neighbors look as uncertain as ever.
Indications so far suggest that President Donald Trump would be loath to continue the détente initiated by his predecessor, which sought to loosen travel restrictions and barriers to trade implemented more than 50 years earlier. During campaigning, the now President tweeted his condemnation of human rights abuses conducted by Cuba's totalitarian government. Then, last week, Cuba's President Raúl Castro made his first public retort, describing President Trump's policies as "egotistical" and "irrational".
However, President Trump also has a pro-business agenda to ally. A number of U.S. companies took advantage of Obama's executive order and efforts to restrict business freedoms will not come easily. Indeed, it would not go unnoticed that Trump built his fortune on the tourism industry and his organization reportedly once sought to pursue possible business interests on the island.
So where does President Trump go from here - and how should business respond?