The aim of this study was to determine the types of choices secondary teachers make when arranging learning environments and to determine how these choices change within the context of educational reforms aimed at the stimulation of New Learning. Interviews held with 15 Dutch secondary teachers showed three aspects of learning environments to which these choices of teachers are primarily related: (1) the division of teacher and learner roles, (2) learning goals, and (3) learning materials. The same three aspects emerged when teachers were specifically asked about arranging learning environments that stimulate New Learning. The interviews showed, however, that teachers have different conceptions of the instructional choices that will stimulate New Learning. In addition, teachers appeared to be thinking mostly in terms of learning products and not in terms of learning processes as a learning goal. Furthermore, teachers showed hardly any attention for arranging cooperative learner roles. For the successful transformation of education in the direction of New Learning, therefore, more support for teachers is recommended.