The use of digital technologies is now a natural part of schoolwork in many schools. The use of digital technologies and the conditions for technology-enhanced learning and school development were studied in two schools, an upper-secondary school and a compulsory school, over a period of 3 years, exploring the student, teacher, school leader, and school perspectives. In this small study, two surveys (N = 26; N = 17) were used to provide further insights into the compulsory school, by exploring the parent perspective of a 1:1 laptop initiative. Laptop use in the classroom was seen as a potential pedagogical tool for structure and support in learning activities, student responsibility for schoolwork, and issues of digital equity. Challenges included increased laptop use, difficulties regarding insight into and monitoring of schoolwork and homework, students’ focus on schoolwork in the classroom environment, and physical aspects. The results show that the parent perspective provides important insights for teachers, school leaders, and school organizers that may help support students’ learning through the use of digital technologies in the classroom.