In the early 1940s, the colonial government of Puerto Rico with the consent of the U.S. federal government began to elaborate a land reform. Under Title V of the Land Law of 1941, the government established resettlement communities for landless families. One of their goals was to transform landless agricultural workers into an industrial and urban labor force by teaching them “democratic, industrial, and modern” habits. Government officials distributed land to landless families through lotteries, portraying the ceremonies as acts of democracy. Community education programs produced literature, films, and posters aimed at fostering development and political participation. The colonial state intended to mold landless workers into new citizens, part of a labor force for industrial manufacture, but land distribution and its effects over the population were uneven, disorganized, and sometimes contradictory. Landless workers and residents of land distribution communities maneuvered within, escaped from, and shaped those government policies.