Teacher educators understand the importance of building strong connections between university coursework and preservice teachers' experiences in the field. However; often the two settings difSer in terms of philosophical and methodological perspectives and practice, presenting teacher education programs with a number of dilemmas. The purpose of this article is twofold. First, we describe our curriculum inquiry process in which we examined and reflected on data collected from cooperating teachers, student teachers, and university student teaching supervisors in the special education teacher certification program at the University of Wisconsin-Milwaukee (U WM). We were guided by a question that had plagued us for several years: How does our teacher education curriculum connect with preservice teachers' experiences in the field? Second, we summarize and discuss the outcomes of our inquiry as dilemmas, which emerged as we considered the experiences and expectations of each of the stakeholders in the student teaching process.