The United States and Cuba moved to end five decades of hostility and agreed to revive diplomatic relations in December 2014 while US President Barack Obama finally made an official visit to Cuba on 20 March 2016 as the first sitting president to do so in 88 years. In contrast with the Cuban case, US–North Korea relations are only getting worse due to the North Korean nuclear program. The United States adopted new legislation for strong economic sanctions against North Korea after the country's fourth nuclear test was carried out on 6 January 2016 and its launching of a long‐range missile on 6 February 2016. This study aims to find an answer as to why Cuba and North Korea are walking different paths in their relationships with the United States even though they have been subject to similar sanctions from the US. Recent analysis shows that factors in security, international and economic surroundings, geostrategic factors and domestic politics contribute to notable divergence between Cuba and North Korea in regards to their relationships with the United States.