This paper details the efforts of four organizations that have been able to negotiate their environments effectively, in the hopes that the analysis provides insights into how organizations are able to establish valuable learning environments for youth in nonschool hours. The negotiation, the process of dealing with various layers of environments and systems, that contributes to the effectiveness of these organizations and their capacity to work successfully with youth. The 4 organizations were selected from 32 organizations in the San Francisco Bay area involved in a study of youth organizations and the learning environments they promote. The four organizations are: (1) a multiservice community center that offers youth of all ages opportunities to participate in a diverse array of programs; (2) a program to help high school youth develop action projects; (3) a community center that draws on community resources and cultural surroundings to run programs in local schools and the neighborhood; and (4) a Boys and Girls Club in a distressed neighborhood. These organizations have been successful in negotiating in external contexts because they have used the neighborhoods as learning resources, learned to work with the schools, and developed collaborative atmospheres in low-income areas. The four organizations look and are quite different, but they have all made choices about supporting youth and creating strong learning environments. The examples in this paper suggest some ways other organizations can make better or more effective choices to support youth development and learning. (Contains 19 references.) (Author/SLD)