This chapter provides technical communication programs and instructors with strategies for developing more effective, sustainable, and community-focused service-learning partnerships. It considers the educational benefits for students, reciprocity is critical to a successful service-learning partnership the activity needs to benefit the organization and must account for the nonprofit's needs, constraints, and timetables. The partnership needs to have sustainability in mind so that if the project runs its course for any number of reasons, the organization has the infrastructure in place to continue whatever service had been rendered by students. Service-learning client projects always involve some amount of chaos simply bringing in stakeholders outside of the university complicates the audiences with whom students are communicating and for whom they are writing. Chaos is inevitable, particularly in service-learning projects engaging small community organizations. In order for teachers to help students learn to handle the complex needs of a real audience, students will need to see the organization's strengths and weaknesses.