The US-Cuban relations have been historically bitter due to various factors, including the US's reluctance to engage with Cuba and its communist ideology. During the Cold War, the US faced difficulties due to Cuba's inclination towards the USSR, leading to the 1962 Cuban Missile Crisis. The US has always had concerns about Cuba and its ideology, which have been reflected in policies and statements. The Obama administration attempted to take positive steps towards Cuba, but the Trade Embargo imposed by the USA in the 1960s still heavily affected the relations. By the 21st century, these issues must be resolved to eradicate security and economic concerns from the region for its prosperity. The Reagan administration reversed direction and focused on controlling Cuban immigration to the US, granting up to 20,000 immigrant visas annually. Cuba has always impacted the security of the United States, as the country has been a significant threat since 1959 when the US and USSR faced nuclear war. The US has attempted to influence many countries in the region, but Cuba has been difficult to crack. Despite imposing embargoes, the US has failed to bring democratic norms to Cuba. As Cubans have a major stake in US politics, the US capitalizes on their influence. The worsening law and order situation in Cuba has led to mass migration to the USA, with the US trying to compensate Cuban immigrants to undermine their government policies. The 21st-century fluctuations in American policy for Cuba continue to pose Cuba as a security threat to the US. This article aims at highlighting issues like Migration, Cuban Ideology, US Embargo, and Terrorism which remain to be at core of the US-Cuban relations. These issues must be addressed in order to put US-Cuban relations back on track.