To contribute to organisational knowledge, Communities of Practice (CoPs) should be nurtured and supported by elements of the wider organisation in which they exist, so reaching across what might be termed organisational 'boundaries'. This chapter reports an action research study of a CoP of tertiary educators, with a domain focus of information technology (IT), which has perceived that their central IT department's support is insufficient to their work requirements. The chapter reports an intervention directed towards boundary spanning, in the form of a facilitated workshop that sought to bring members of the CoP and a key representative of the central IT department together, to share roles and challenges, leading to the generation of a list of issues and an action plan. Amongst a number of insights gained, it is concluded that when seeking to facilitate the spanning of boundaries between a CoP and the wider organisation in which it exists, it must be understood that boundaries are multi-dimensional and that cultural differences must be appreciated and addressed. Further, it becomes apparent that the appointment of staff to facilitate communication does not constitute, in itself, a resolution of communication problems. Finally, as demonstrated in the case of the CoP under study, changes in the strategic direction of the immediate organisational unit within which the CoP resides can substantially change the need for and nature of interactions between a CoP and the wider organisation, over a relatively short time span.