Digital storytelling (DST) dovetails well with facilitative teaching and is frequently lauded as an avenue to positive outcomes within and outside of educational institutions. Ascribed results include empowering marginalized voices, building community and fostering engagement, deepening cultural identity and understanding, engendering empathy, and facilitating dialogue. In my experience as a community practitioner and as an educator, I have witnessed many of these transformative impacts. A setting in which diverse university students and international service employees work together in learning partnerships seems an ideal scenario for DST and its attendant benefits. Nevertheless, I have developed some hesitancy regarding my use in the context just mentioned, and of education's perhaps indiscriminate embrace of digital storytelling. In this paper, I first characterize the genre, reflect on the complementary resonance of the form with facilitative teaching, and locate digital storytelling within the spectrum of educational philosophy. Next, I describe my teaching context with undergraduate students mentoring employee adult learners, provide examples of my experiences with media-making, and problematize co-creative digital storytelling. [For the full proceedings, see ED665621.]