This paper examines and analyses where and how information and communication technologies (ICT) are integrated in Singapore schools to engage students in higher-order thinking activities. Taking the activity system as a unit of analysis, the study documents the actual processes and sociocultural elements that engage students in higher-order thinking. By employing methods such as observations, focus group discussions with students, and face-to-face interviews with teachers, ICT-coordinators and principals, an account of how the activity systems within and between classrooms, and the schools are generated. Based on the analysis of the data from 10 schools, issues in the learning environment are discussed: Necessary (classroom management and orienting activities) and sufficient conditions (scaffolding activities and supporting school policies) for effective ICT integration in the classroom. The account 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 by supporting school policies in the larger sociocultural setting of the school. This account provides a sample of pedagogical and sociocultural issues that are discussed over the course and at the end of the project. Like a good guidebook, the study sensitizes the audience to what is likely to happen given a particular objective, constraint, or design.