This is a qualitative research report that interrogates the extent to which Web 2.0 (interactive and social medial tools)  and other digital technologies are being used in the Community Work sector in the GTA. Simultaneously the project examines students’ digital capabilities and training. The research findings are based on 21 cross-sector agency interviews and a combined total of 104 students across two different years of study. The findings speak to the need for critical digital fluency in pedagogical approaches to help students gain literacy but also have the flexibility to adapt as the tools shift and change and a recognition that non-profit agencies rely on these tools for a different types of work, concluding with suggestions on how GBC can best support both curriculum development and our non-profit partners in an era digital transformation.