This paper discusses the findings of two case studies (two primary schools in Singapore), which are part of a larger research study, that aims to examine and analyze where and how information and communication technologies (ICTs) are integrated in Singapore schools to engage students in higher order thinking activities. For students to engage in higher order thinking, they first need to have autonomy over their learning processes. The focus of the paper is on how orienting activities support learner autonomy in the ICT-based learning environment. Taking the activity system as a unit of analysis, the study documents the actual processes by which orienting activities are planned and organized to support learner autonomy in their contexts. By employing methods such as observations, focus group discussions with students, and face-to-face interviews with teachers, an account of how the activity systems within and between classrooms, and the schools are generated. The account identifies and describes five categories of orienting activities: introductory sessions to ICT tools, advance organizers and instructional objectives, worksheets and checklists, dialogues among participants, and tools for post-instructional reflection. It also highlights the constraints of time and lack of knowledge and experience in the contexts that the teachers are working under, and how these constraints are addressed.