Community-based organizations (CBOs) can help students gain a broad understanding of the relationship between education, work, and community. CBOs are frequently able to expand the scope of school-to-work by providing opportunities for young people to address community issues and by incorporating a unique youth perspective into the development of school-to-work opportunities. Potential roles for community-based organizations include the following: (1) helping create, implement, and manage the school-to-work system; (2) securing community involvement; (3) providing work-based learning; (4) serving at-risk and out-of-school youth; and (5) providing access to support services. Strategies for engaging CBOs are as follows: challenging assumptions, bringing all stakeholders to the table, taking a participatory approach to agreeing on goals and roles, building on existing partnerships, and taking time to build trust. Examples of effective practices include the Academy of Manufacturing and Engineering Technology in Minneapolis (Minnesota) and the Diploma Plus Program in several Massachusetts communities. (Resources listed include 12 organizations and 12 publications.) (KC)