The assessment of learning in the ethical domain is one of the most complex aspects to attend in the educational context. In recent years, character education has contributed greatly to different social disciplines, such as education or nursing. However, the development of this approach has run up against several obstacles and limitations, as there is little evidence regarding its long-term effectiveness or its evaluation. This essay aims to identify some of the main difficulties to assess learning in the ethical domain, as obstacles and possible constraints to Aristotelian-based character education. Methodology is analytical and of a philosophical-educational nature, based on which an argumentative analysis is constructed from the bibliographical review of the contributions of classical and contemporary authors. Results show the existence of four major problems and ten associated subproblems, both of an external nature linked to the contextual factors of assessment, and of an internal nature that affect the essence of the process itself, which highlight the difficulty of carrying out assessments of an ethical kind. Far from proposing a pessimistic position, we argue a realistic vision that allows educators at different educational levels to be aware of the limits and critical points of evaluation in the ethical domain.