Existing research offers limited insight into how digital transformation unfolds in Social Enterprises (SEs). This study examines what drives SEs to engage in digital transformation, the facilitating and hindering factors, and work-related risks. Drawing on a theoretical framework integrating Dynamic Capabilities, Digital Social Innovation enablers and barriers, and Corporate Digital Responsibility, it adopts a qualitative multi-method case study based on a group interview and a focus group with managers from Italian SEs. The findings show that digital transformation is filtered through SEs’ anthropocentric orientation. In the SEs studied, it is triggered by concrete organizational and social needs and leads to a reconfiguring process tailored to mission preservation. More specifically, digital transformation unfolds through processes of sensing, seizing, and reconfiguring, in which organizations identify unmet social and organizational needs, adopt technologies through gradual and context-sensitive approaches, and adapt internal structures, competences, and external partnerships over time. Digital transformation depends on a combination of human, organizational, and environmental factors, with hybrid competences, bottom-up experimentation, and ecosystem collaboration emerging as key enablers, while resource constraints, uneven digital literacy, and resistance to change pose obstacles. These barriers are not only structural but also reflect concerns related to service quality, inclusion, and mission coherence. The implications of digital transformation for work are actively filtered through mission-oriented values and responsibility-oriented practices, while digital technologies are predominantly framed as tools for mission augmentation rather than work substitution. In this respect, digital transformation in SEs appears to be governed through embedded responsibility-oriented logics, which shape how risks such as dehumanization and job displacement are anticipated and managed. Overall, the study contributes to research on digital transformation by showing how anthropocentric, mission-driven organizations interpret and enact digital change. It also suggests that other sectors may learn from SEs that maintaining a human-centered approach can help mitigate ethical and organizational risks associated with digital transformation.