In this chapter, we consider the development of an emerging 'Teaching with Technology' staff development model dedicated to growing active educator Communities of Practice (CoPs). This work is led by a team at the Centre for Educational Technology at the University of Cape Town. The activities organised to grow the community include workshops, seminars, teaching and research partnerships. The project extends across several faculties to grow a cross-faculty community of educators who teach with technology. By August 2006 over 240 educators had attended one or more of the workshops and seminars. The multifaceted combination of activities and staff support systems has yielded growth in the domain, community and practices largely through the effective facilitation of boundary experiences. In this context, the staff development professionals and several educators who are also consummate boundary professionals have been acting as brokers. Three boundary vignettes from interactions with educators who have learnt new practices serve as illustrations of these processes.