Despite university supervisors’ critical role in the success of PK-12 teacher candidates, research is limited on how to best prepare supervisors to mentor their supervisees and interact with cooperating teachers and school administrators. By using two surveys and a focus group meeting, this qualitative study explores supervisors’ experiences to surface dilemmas of supervisory practice. Results indicate supervisors suffer overwhelming workloads, feel marginalized by their institutions, lack ongoing training, and are often unclear as to what their role is. The success of the cadres of clinical supervisors ultimately depends on training, but more crucially on full engagement by their home institutions.