The Maleconazo was a protest on 5 August 1994, in which thousands of Cubans took to the streets around the Malecón in Havana to demand freedom and express frustration with the government. Following the collapse of the Soviet Union in the early 1990s, Cuba fell into a crippling economic crisis that had many citizens looking to flee the island. On the day of the protest, the Cuban police blocked people from boarding tugboats leaving Havana, prompting thousands of citizens to storm the streets in the largest anti-government demonstration Cuba had seen since the Cuban Revolution. In the following weeks, President Fidel Castro quelled the frustration by opening the doors of the country and allowing Cubans to leave, which had a significant impact on Cuba's relationship with the United States moving forward.

The Special Period, officially the Special Period in the Time of Peace, was an extended period of economic crisis in Cuba that began in 1991 primarily due to the dissolution of the Soviet Union and the Comecon. The economic depression of the Special Period was at its most severe in the early to mid-1990s. Things improved towards the end of the decade once Hugo Chávez's Venezuela emerged as Cuba's primary trading partner and diplomatic ally, and especially after the year 2000 once Cuba–Russia relations improved under the presidency of Vladimir Putin.