Conceptualization and the practice of alternative assessments in the context of general assessment practices in mathematics have wide-ranging significance to learning and teaching. Yet little is known about how South African teachers choose assessment tasks and how it links to their teaching. This paper reports on a case study of five grade 10 mathematics teachers, chosen from five different schools. Data were collected through interviews and analysis of samples of assessments. Ernest's categorization of educators' philosophies and Boesen's classification of competences were used as theoretical frameworks for the analysis of samples of assessments and interviews. The educators' choice of alternative assessment strategies was found to be more of a gesture of compliance with what has been advocated in the Outcomes-Based Education curriculum, rather than a concerted effort to embrace principles of educational reform. Though the teachers' discourses were more inclusive of progressive perspectives on the purpose of assessments, their actual assessment practices still remained within the confines of traditional procedural tests.