In Cuba, anarchism took root between the late 19th and early 20th centuries. Its history traces back to the involvement of both anonymous and prominent militants in the struggles for the abolition of slavery in 1886 and the war for independence in 1895. From the formation of cultural clubs, guilds, artisan associations, and unions to the convergence of many libertarians in organizing the M25J, which overthrew Fulgencio Batista's dictatorship in the late 1950s, anarchists played a significant role in shaping the country's popular political sphere. In the years leading up to the Cuban Revolution, they were active on multiple fronts, including unions, student movements, and political resistance groups. Between the 1940s and 1960s, anarchist organizations were crucial in mobilizing popular support and spreading libertarian ideas. Cuban anarchists established connections with other social and political movements, including communists, socialists, and nationalists, demonstrating a genuinely anti-dogmatic attitude aimed at toppling Batista's dictatorship. During the armed phase of the Cuban Revolution, many anarchists joined the ranks of rebel groups fighting in the mountains and cities against the regime. The presence of anarchist organizations and militants in the dynamics that led to the Cuban Revolution is an emblematic yet overlooked aspect of Cuban history and the broader revolutionary movement of the 20th century. By examining the role of anarchists in this context, we hope to gain valuable insights into the political, social, and ideological disputes and frictions that shaped contemporary representations of the Cuban Revolution. Furthermore, analyzing the active presence of anarchists in this historical process can provide unique perspectives on the potential and challenges faced by libertarian movements in contexts of social and political change, as well as the specific contours of the autonomy project that could have been experienced by Cuban society.