This paper reports an analysis of the tasks included in the Mathematical Challenges book. The analysis was based on the proposals of the Authentic Intellectual Work (AIW). The purpose of the study focuses on assessing the potential of the mathematical challenges to promote in-depth and meaningful learning through the connection with different contexts, and other features including purpose, multiple-solution pathways, construction of knowledge and higher order thinking. Participants in this study were 3 elementary school teachers, 2 mathematics specialists and the authors of this paper; they assessed the Mathematical Challenges through a questionnaire based on specific rubrics. The study used a mixed methods approach. The analysis produced two main findings. First, challenges vary in their connections to students' lives according to the context they come from. Second, almost all mathematical challenges are related to the highest levels of others AIW criteria.