The objective of this paper is to discuss aspects of high school students' learning of probability in a context where they are supported by the statistical software R. We report on the application of a teaching experiment, constructed using the perspective of Gal's probabilistic literacy and Papert's constructionism. The results show improvement in students' learning of basic concepts, such as: random experiment, estimation of probabilities, and calculation of probabilities using a tree diagram. The use of R allowed students to extend their reasoning beyond that developed from paper-and-pencil approaches, since it made it possible for them to work with a larger number of simulations, and go beyond the standard equiprobability assumption in coin tosses.