Based on findings from a semester-long study, this article examines the development of Samoan prospective teachers' mathematical understandings and mathematics attitudes when investigating authentic contexts and applying working mathematically processes, mental computations and problem-solving strategies to find solutions of problems. The prospective teachers had enrolled for the "second" time (having failed their first attempt), in the first-year mathematics methods course of a 2-year Diploma of Education (Primary) programme. The group also included those enrolled in the Diploma of Education (Early Childhood and Special Needs) programmes, who recognizing their own limited understanding of mathematics would ordinarily shy away from opportunities for improvement. Given the negative mathematical and learning experiences, this group was ideal to engage in innovative and creative approaches that would make mathematics learning more meaningful and contextual in a Samoan environment. Only data from the attitudinal questionnaires and interviews are presented in this article. Main findings have implications for teaching and learning mathematics.