The article analyses a collaborative effort of learning across workplace boundaries in a regional learning network of South Savo, Finland. The focus is on the "Forum of In-house Development" in the network. Our objective is to highlight a dialectical approach to boundaries that draws from the ideas of cultural-historical activity theory. Expansive transformation may be explored through the expansion of socio-spatial and instrumental-developmental boundaries. This is shown through four transitional episodes that reveal the expansion of the object of learning. We argue that crossing the socio-spatial boundary of a workplace is not a sufficient condition, but that new meditational means created at the instrumental-developmental boundary are needed to expand workplace learning and development in challenging and complex regional contexts. (Contains 1 table and 1 figure.)