School leaders' practices to support the innovative use of digital technologies for teaching and learning and the conditions for technology-enhanced learning were studied in a 1:1 laptop initiative in two schools over a period of 3 years in Umeå, Sweden. The aim of this paper is to explore, analyze and discuss the possibilities and challenges in the final phase of this 1:1 initiative from the perspective of the school leader. The school leaders saw possibilities in new methods of working, sharing and collaboration, and created a beneficial environment for the use of digital technologies in teaching. The challenges were technical problems, supporting teachers in their work, and finding time to prioritize leadership for the use of digital technologies. How school organizers support school leaders' practices in creating beneficial conditions for technology-enhanced learning will be important for how school leaders' practices support, promote, and advance innovative and sustainable teaching and learning environments through the use of digital technologies.