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Prostitution in Cuba has always been a legal profession, though it has periodically been regulated or repressed. Many Cubans do not consider the practice immoral. Sex trafficking is a problem in the country. The country, and Havana in particular, has often been associated with prostitution in foreign eyes. A public debate followed concerning the relationship between the changes in the city's demographics and the levels of prostitution in the city.
After the Spanish—American War , there were attempts to set up "zonas de tolerancia", effectively red-light districts for commercial sex. However, they were not officially classified as prostitutes, but instead treated as criminals guilty of the crime of sodomy. A major industry grew up around them; government officials received bribes, policemen collected protection money.
Prostitutes could be seen standing in doorways, strolling the streets, or leaning from windows". It drew upon a tradition of exoticising mixed-race Cuban women which originated in the work of male Cuban writers, artists, and poets. Following the Cuban Revolution in , the new Cuban government saw prostitutes as victims of corrupt and foreign capitalism,  and viewed prostitution itself as a "social illness", a product of Cuba's pre-revolutionary capitalist culture, rather than a crime.
In , pimping was outlawed. Prostitution itself remained legal, but the government, assisted by the Federation of Cuban Women , attempted to curb it. A census of the sex industry was conducted in , identifying , prostitutes and 3, pimps. Women who wished to leave prostitution were given training courses and offered factory jobs. Most of the remaining private businesses on the island were nationalised.
Following the dissolution of the Soviet Union in the early s, Cuba experienced economic depression resulting from the loss of income from Soviet trade. This Special Period saw the re-introduction of elements of market capitalism into the Cuban economy, and prostitution re-appeared. The possession of US dollars became a primary route to prosperity, and prostitution was an avenue used by many women to obtain them.