This paper details one scholar’s experience of becoming a practitioner in her area of expertise: technology for schools in developing world contexts. After being invited to design a solar powering system to charge donated laptops in Haitian schools, she began working with students in hands-on, project-based courses to design and deploy ICT4D-related technologies in the field. Once on the ground, she and her students discovered that the challenges and failures from playing such an active role can be many, but the speed and intensity with which one learns on-site is much greater than from more traditional types of classroom-based or “book learning.” After shifting geographic focus to Pacific Island schools, the author and her students designed, developed, and deployed multiple new technologies, including a solar computer lab in a box and a solar digital library. Throughout this venture, unexpected developments continually arose, which have led to the changing of project partners, improvement of the relevance and usefulness of technology being developed, and an expansion of the project to multiple small island-nations. Through a narrative case study of experiential learning, both in the-classroom and in-the-field, this paper details the challenges and lessons learned from the scholar practitioner’s experience.