This chapter discusses some strands of experimental mathematics from both an epistemological and a didactical point of view. We introduce some ancient and recent historical examples in Western and Eastern cultures in order to illustrate how the use of mathematical tools has driven the genesis of many abstract mathematical concepts. We show how the interaction between concrete tools and abstract ideas introduces an “experimental” dimension in mathematics and a dynamic tension between the empirical nature of the activities with the tools and the deductive nature of the discipline. We then discuss how the heavy use of the new technology in mathematics teaching gives new dynamism to this dialectic, specifically through students’ proving activities in digital electronic environments. Finally, we introduce some theoretical frameworks to examine and interpret students’ thoughts and actions whilst the students work in such environments to explore problematic situations, formulate conjectures and logically prove them. The chapter is followed by a response by Jonathan Borwein and Judy-anne Osborn.