This paper examines the evolution of Cuba's self-employed entrepreneurs since the sector became an officially-recognized alternative to State sector employment in 2010. Despite the expansion of authorized self-employment activities and the implementation of gradual economic reforms to "update" the country's socialist economic model since 2010, Cuba's emerging self-employed entrepreneurs still face a series of constraints and limitations, such as an onerous tax system, underdeveloped banking and financial sectors, lack of access to organized input markets and a still hostile business climate that hinder their ability to expand and contribute to the country's economic growth.