Storytelling is one of the earliest forms of knowledge transfer, and parents often use it for teaching their children values and knowledge. Formal schooling, however, is less inclined to use storytelling as a vehicle for knowledge transfer, and even less as a vehicle for modern self-directed, student-centered, and constructionist pedagogy. Research literature reports experiences on student-centered storytelling in schools, but there is little information about such learning environments using modern information technology. Using a case study approach, we collected qualitative data from a workshop that tested a number of constructionist pedagogical approaches and one-to-one computing technology in a hypercontextualized storytelling workshop. In that workshop, which took place in a Tanzanian primary school, pupils used their XO-1 laptops as digital media tools for expressing their dreams and solutions to overcoming challenges in life. Results of this study suggest that digital storytelling offers additional advantages when compared to traditional storytelling. Designers need to follow six principles for a successful digital storytelling workshop: commitment, contextual grounding, previous exposure to the context, involvement of local experts, atmosphere of trust, and realistic flexible planning. (Contains 3 tables and 6 figures.)