This thesis concerns the challenge of integrating dynamic software environments into the teaching of mathematics. It investigates particular aspects of the design of tasks which employ this type of computer-based system, with a focus on improvement, both of the tasks themselves and of the design process through which they are developed and refined. The thesis reports two research projects: a small initial one preceding a larger main project. The initial case study, involving two graduate students in mathematics, develops a task design model for geometrical locus problems. The main study constitutes the first iteration of a design-based study, conducted in collaboration with four upper-secondary school teachers and their classes. It seeks to identify task design characteristics that foster students’ mathematical reasoning and proficient use of software tools, and examines teachers’ organisation of ‘follow-up’ lessons. The findings concern three particular aspects: features of tasks and task environment relevant to developing a specific plan of action for a lesson; orchestration of a particular task environment to support the instrumental genesis of specific dynamic software tools; how to follow up students’ work on computer-based tasks in a whole-class discussion.