On April 19, 2011, Cuba made the most significant change to its leadership in over 50 years, by appointing José Ramón Machado to fill the second-highest position in the Communist Party. It was the first time since the 1959 revolution that someone other than the Castro brothers has been named to the position. The appointment was made at the partys first congress in 14 years and coincides with several changes being made to allow for more private enterprise in Cuba.

In October 2011, buying and selling cars became legal. Also, Raul Castro started allowing Cubans to go into business for themselves in a variety of approved jobs, from accounting to food vendors. The following month, the government began allowing real estate to be bought and sold for the first time since the days immediately following the revolution. A new law, applying only to permanent residents, went into effect on November 10. The law, an effort to prevent massive real estate holdings, limits Cubans to owning one home in the city and one in the country. The new law also requires that all new real estate transactions be made through Cuban bank accounts for regulation purposes.

In December 2011, the government pardoned more than 2,900 prisoners. Of those pardoned, 86 were foreigners; however, Alan Gross was not one of them. Gross, an American contractor, has served a 15-year sentence since 2009 for distributing satellite telephone equipment in Cuba. His case has dampened President Obamas efforts to improve relations between the United States and Cuba.