Capstones form an important part of the curriculum in many undergraduate and graduate programs in Information Systems. These projects give the students a chance to synthesize and apply the skills they have been acquiring throughout their academic program. These projects can be integrated with another recent initiative in higher education: service learning. By turning the capstones into "real-world" projects for external clients, the students can give back to the community while completing a valuable learning experience. However, these real world exercises sometimes take on real world characteristics- like failure. How do we, as professors, guide students through a service learning capstone to completion, despite the external challenges that come with it? How can we evaluate the outcome of these projects, when we know success may not be a part of the final product? The authors draw on personal experience with service learning capstones to address this problem.