This chapter discusses the didactical potential of the learner-generated mathematical content that emerged in the first implementation of the didactical situation. The didactical situation required involving technical expertise, particularly for coordinating the Web and mobile technologies for the indoor presentations and arranging the setup for the tasks with augmented reality (AR). The didactical situation was organized as a sequence of learning activities distributed across four different contexts: devolution, adidactical situations, institutionalization, problem-solving with AR. Teachers often have limited resources to design and implement innovative didactical situations that involve mobile technologies. For this reason, special attention to designing the introduction of mobile technologies should be paid during the devolution phase and the use of multiple technologies in the institutionalization phase. The customized mobile and Web applications served two purposes in the didactical situation-namely, to facilitate adidactical situations in the outdoor context and to enable mathematical communication in the indoor context.