To prepare students for competent practice in increasingly technology-enabled settings, social work curricula must provide ample opportunities for developing digital literacy. Incorporating digital stories as course assignments offer educators one promising approach. Despite the fact that digital stories can provide a powerful teaching strategy and meaningful learning experience for students, they have received little attention in the social work education literature. This study explored implementation of a digital story assignment in three social work courses and examined undergraduate and graduate students' appraisals of the assignment and learning outcomes. Qualitative findings indicated high satisfaction and learning associated with key social work competencies such as digital literacy, group work, and advocacy. Students valued the novel opportunity for creativity and collaboration, and were challenged in positive ways to produce high quality work that could be shared with a public audience. Key challenges identified by students included a steep technology learning curve, some technology resistance, and limitations associated with group projects (e.g., group dynamics). Overall, however, these exploratory findings suggest that digital story assignments can offer a timely and useful tool for social work educators to enhance engagement and learning, foster advocacy practice skills, and build digital literacies needed in the 21st century practice landscape.