Soviet troops began to withdraw from Cuba in September 1991 over the latter’s objections that the withdrawal would compromise the island’s security. When the Soviet Union dissolved later that year, the already troubled Cuban economy suffered further from the loss of vital military and economic support that had, in effect, constituted subsidies. Amid severe internal shortages, and with unrest and dissatisfaction growing, Castro declared a “special period in peacetime” of food rationing, energy conservation, and reduced public services. Unemployment increased, and shortages of food, medical supplies, raw materials, and fuel were exacerbated by the ongoing U.S. trade embargo.

In 1993 the government legalized small businesses such as paladares (family restaurants), private employment, and the use of U.S. dollars (notably remittances from abroad) in Cuba. The following year independent farms and farmers’ markets were encouraged. The government also attracted foreign capitalists, including Canadian and Spanish hoteliers. Christmas was restored as a national holiday in 1997, in anticipation of what turned out to be a highly successful visit by Pope John Paul II the following year. The economy improved markedly, led by the tourist sector, but many Cubans began to question the future of socialism.

In 1996, after Cuba shot down two small aircraft piloted by a Florida-based anti-Castro group, the U.S. Congress passed the Helms-Burton law, which threatened sanctions against foreign-owned companies investing in Cuba. In 1999 prominent dissidents in Cuba were jailed and repressive laws enacted, prompting further international criticism. In the early 21st century, Cuba benefited from a petroleum-trade agreement with Venezuela and eased some of its more restrictive economic and social policies.

Although Castro maintained a firm grip on power, speculation grew outside Cuba on the state of his health, especially given his advancing age. Increasing attention was focused on his brother and designated successor, Raúl Castro Ruz, who was also the head of the armed forces, and Ricardo Alarcón de Quesada, the influential president of the National Assembly. Indeed, on July 31, 2006, Fidel Castro passed power on a provisional basis to Raúl in order to recover from a serious intestinal illness. In February 2008 Fidel Castro officially announced that he would not accept another term as the president and commander in chief of Cuba, a position that he had held for 49 years; Cuba’s National Assembly chose Raúl as Cuba’s new leader.

Soon after the transfer of power to Raúl Castro, Cuba abolished its equal pay system, removing wage restraints that had been in place since the early 1960s. Other reforms were implemented as well, with Cubans being allowed to purchase cellular phones and personal computers and to stay at hotels formerly reserved for foreigners. The European Union, which had imposed sanctions against Cuba in 2003 for its repression of dissidents, lifted the sanctions in June 2008, a move that was criticized by the United States.

Representatives of the Roman Catholic Church and Spain negotiated with the Cuban government in 2010 for the release of 52 political prisoners. The dissidents had been imprisoned as part of a 2003 crackdown on journalists and activists who, according to Fidel Castro, had been undermining the Cuban government on behalf of the United States. Although the government issued no statement about the negotiated release, seven of the prisoners were freed in mid-July 2010 and immediately sent to Spain.

In September, only days after Fidel Castro had told an American reporter that “the Cuban model doesn’t even work for us anymore,” Raúl Castro announced new official toleration of private enterprise and the layoff of some 500,000 government employees. In August 2011 the National Assembly approved a new set of measures that further opened the economy. Among those steps was a reduction of the state’s role in the agricultural, construction, transportation, and retail sectors, along with yet more encouragement for the development of private business. As many as a million more jobs were targeted to be cut, especially from the country’s gigantic bureaucracy. The draconian travel restrictions that had been in place since the revolution were also revised. Perhaps the most dramatic change of all was the announcement that the buying and selling of private property would be legalized at the end of the year. By the middle of 2012 it was estimated that some 390,000 Cubans had embarked on a myriad of self-employment enterprises (cuenta-propistas), including everything from beauty parlours and auto-repair firms to taxi services and restaurants. After being elected to a second term as president in February 2013, Raúl Castro announced that he would not seek to return to that office at the end of his term in 2018.

Throughout 2013 the Cuban government implemented new measures designed to provide short-term economic relief and meet long-range political goals. Among the most important of the reform measures was the liberalization of restrictions regulating foreign travel, which no longer required Cubans to obtain official authorization or a letter of invitation from a person or an institution abroad. The new terms of travel also increased the maximum length of time residents could remain away from the island to two years—or longer. Moreover, expatriate Cubans could return to the island and reside for periods as long as three months at a time. The number of state-operated enterprises that were transferred to private ownership also grew markedly.

A handshake between Raúl Castro and U.S. Pres. Barack Obama in December 2013, at a memorial for South African leader Nelson Mandela, offered symbolic new hope for improved Cuban-U.S. relations that bore fruit almost exactly one year later. On December 17, 2014, both leaders appeared before national television audiences to announce the restoration of diplomatic relations between their countries that had been in abeyance for more than 50 years. The policy change was agreed to in phone conversation between the two leaders and came after 18 months of secret negotiations that had been fostered by the Canadian government and Pope Francis I. The revelation was accompanied by the release of three Cuban intelligence agents who had been jailed in the United States since 1998, a U.S. intelligence agent who had been captive in Cuba for nearly 20 years, and Alan Gross, a subcontractor for the U.S. Agency for International Development (USAID), who had been held in Cuba since 2009 after being convicted of importing illegal technology and attempting to establish secret Internet service for Cuban Jews. In his speech, Castro emphasized the necessity of removing the U.S. economic, commercial, and financial blockade of Cuba, which, because it was codified by U.S. law, was subject to congressional action and beyond the scope of Obama’s executive authority. Nonetheless, the American president was able to mandate a review of Cuba’s status as a state sponsor of terrorism and to ease some travel and financial restrictions.

In 2015 the two countries officially reopened their embassies in each other’s capitals. On July 20 in Washington, D.C., U.S. Secretary of State John Kerry marked the occasion by meeting with Cuban Foreign Minister Bruno Rodríguez, and the Cuban flag was hung among those of more than 150 other countries in the lobby of the U.S. State Department. In Havana the July opening of the U.S. embassy was somewhat low-key, but a more dramatic ceremony followed there when Kerry visited in August.

Of much greater import was Obama’s visit to Cuba in March 2016, the first by a sitting U.S. president in nearly 90 years. After the visit, however, Fidel Castro castigated Obama for failing to acknowledge the accomplishments of the Cuban Revolution. Moreover, in April Raúl Castro cautioned that the United States was using its advocacy of Cuba’s growing private sector to undermine the Cuban system. Meanwhile, a growing number of Cubans, anxious for faster change, sought to reach the United States, fearing that favourable immigration rules might change.

On November 25, 2016, Cuba was shaken by the death at age 90 of Fidel Castro. Even after relinquishing power to Raúl in 2006, Fidel had remained a prominent figure both in Cuba and on the world stage. He outlived six of the U.S. presidents who served during his reign.

November 2016 also marked the first accounts of a mysterious malady that began afflicting U.S. embassy staff members and their families in Havana. After reporting hearing high-pitched cricketlike sounds in their homes and in two Havana hotels, the American diplomats and their relatives suffered headaches, hearing loss, memory problems, and other symptoms usually associated with concussions. Doctors were at a loss to explain the cause of the distress, but the administration of new U.S. Pres. Donald Trump blamed the illness on “sonic attacks” by the Cuban government, which roundly denied the allegations. In response to the incidents—which continued occurring until August 2017 and resulted in 24 Americans being diagnosed with mild traumatic brain injuries—staffing at the embassy was reduced to skeleton levels. In early 2018, staffers of the Canadian embassy in Havana began experiencing similar health problems.

In the meantime, Trump, who had opposed the normalization of relations between the U.S. and Cuba during his campaign for the presidency in 2016, began rolling back some of Obama’s initiatives. In November 2017 the Trump administration imposed new travel restrictions on U.S. citizens and forbade them from conducting business with stores, hotels, and other entities linked to the Cuban military and security and intelligence communities.

After serving as president for nearly a dozen years, Raúl Castro planned to step down from that office at the end of his second five-year term in February 2018. In December 2017, however, he delayed his retirement until April 2018 so that he could oversee the government’s response to the damage wrought by Hurricane Irma (the first category 5 hurricane to hit Cuba in more than eight decades), which had buffeted the island’s northern coast in September 2017. On April 19, 2018, Castro stepped down as president, though he remained chairman of the Communist Party. On that day the National Assembly confirmed Castro’s handpicked successor and the only official candidate to replace him, First Vice Pres. Miguel Díaz-Canel, who was the first non-Castro to serve as president in more than 40 years. (Fidel had ruled the country from 1959 but did not become president until 1976.) At age 57, Díaz-Canel represented a shift away from the generation of leaders who had participated in the revolution.

Constitutional reform had been on the table since at least 2013, and in June 2018 the formal process of drafting a new constitution began. Contributions from the drafting commission, the government, the National Assembly, and the Communist Party resulted in a first draft that was approved by the National Assembly in July and turned over to the populace for some three months of public debate. According to the government nearly 112,000 Cubans participated in discussions of the proposed document. The most notable modification to arise from this process was a rollback of the sanctioning of same-sex marriage, which came at the behest of Evangelical Christians and some sectors of the Cuban Catholic Church.

The final draft—approved by 87 percent of those who participated in the constitutional referendum in February 2019—reaffirmed Communist dominance through the perpetuation of a single-party state grounded in socialist principles, but it also acknowledged the role of the market and recognized the legality of private property, private business, and foreign investment. The new constitution also established term limits for the presidency (two five-year terms) and reinstated the office of the prime minister (appointed by the president, charged with the day-to-day operations of the government), absent from Cuban government since the 1970s. Although voters had overwhelmingly approved the new constitution, some 15 percent of Cuban voters refrained from participating in the referendum, an indicator of their dissatisfaction with the document and a reflection of the growing willingness on the part of some to challenge the government’s authority, a pushback that no doubt owed much to the spread of Internet use in Cuba and the resultant sharing of information and opinion.

Having benefited greatly from the tremendous influx of U.S. tourists as a result of the Obama administration’s easing of travel restrictions, the Cuban economy was buffeted by the reimposition of restrictions under Trump. That blow magnified the ill effects of a significant decline in the supply of cheap oil from Venezuela that had begun in the mid-2010s as a result of diminishing Venezuelan production caused largely by mismanagement. That decline had forced Cuba to ration electricity and to divert precious hard currency to purchase oil from other sources, leading to reduced imports and the worst food shortages in decades. Those consequences had been mitigated somewhat by the influx of U.S. tourist dollars; however, yet another round of travel restrictions by the Trump administration and its imposition of sanctions on companies that shipped Venezuelan oil (meant to punish the increasingly authoritarian regime of Nicolás Maduro) dealt a crippling blow to the Cuban economy. When the arrival of the coronavirus SARS-CoV-2 global pandemic in 2020 forced Cuba to close its borders to tourists in an attempt to limit the spread of the potentially deadly virus, the Cuban economy went into a free fall, and GDP that year nose-dived by 11 percent.

Notwithstanding the impact of the pandemic on its economy, Cuba initially responded better to the public health crisis than many other countries, largely as a result of strict adherence to the stringent social-distancing and lockdown measures implemented by the government as well as to the closing of the island to travelers. By September Cuba had registered fewer than 6,000 cases of the virus (which had originated in China in December 2019), and only 122 deaths were attributed to COVID-19, the disease caused by the virus. However, after the country was reopened to international flights in November without requiring negative tests for the virus of visitors, the spread of the virus took off. In January 2021 alone, more 15,000 cases of the virus were reported. Some officials argued that the spike actually had been brought about by the relaxation of people’s vigilance to prevention protocols. Whatever the cause, the Cuban health system that was the pride of the revolution was suddenly put under great stress. Not only was there a lack of personal protective gear for health care workers, but also there was a shortage of medical professionals. For years Cuban doctors sent by the government to work in other countries had been a leading source of hard currency for Cuba, but now the presence of many health care workers abroad had left Cuba shorthanded during the pandemic crisis. Moreover, Cuba was not able to afford the foreign vaccines that had been developed to combat the virus, but because U.S. trade embargoes had long since forced Cuba to develop its own pharmaceutical industry, the need for the country to produce a vaccine itself was not an insurmountable challenge.

Despite the challenges facing the country as a result of the pandemic, Castro honoured his pledge to step down as secretary-general of the party at the Eighth Congress of the Communist Party of Cuba in April 2021. He did so saying that he was retiring with a sense of having “fulfilled his mission and confident in the future of the fatherland.” He was replaced as secretary-general by Díaz-Canel.