This study investigates whether participating in digital storytelling (DST) activities improves language learning and the technical computer skills required for this type of project. Moreover, the present investigation also directly explored the learning benefits and elements of contextualization derived from maintaining a personal digital learning narrative (PDLN). Participants were given a term project as group work that involved creating collaborative digital stories. Each group member took responsibility for the group DST projects and concurrently reported contextual personal elements into their PDLNs. A mixed methods methodology was applied to investigate the learning outcomes of the digital story project in terms of language learning and technical knowledge of DST and to explore elements of contextualization that emerged in the PDLNs during student preparation for the collaborative tasks. The findings reveal improved performance on the DS vocabulary and comprehension test, and the DST knowledge test. In addition, elements of contextualization were identified as fitting into three subcategories: the use of the technology at hand, the story text, and spatiotemporal details during the realization of the group project. In addition, feelings of determination, frustration, and motivation were observed through self-reports, classroom notes, videos, and student narrations from the PDLNs.