Many aspects of the institutional life and organizational functioning of psychoanalysis deal with and are affected by evaluation. This paper focuses on one manifestation of this difficulty, namely the evaluation of candidates in psychoanalytic training. Opinions vary regarding its place, necessity, and contribution. Although it is at least nominally practiced in many institutes, it is nonetheless fraught with difficulty. We explore some of the sources and nature of what hampers the function of evaluation of candidates, employing Bion’s Basic Assumptions and their effect on institutional dynamics. Related issues include the ambiguity surrounding the role and authority of the supervisory role and the present theoretical diversity. The role and function of the supervisor is central to this evaluation and focal in our discussion. Our presentation draws on and makes use of the findings of the EPF End of Training Evaluation Project (ETEP).