Students in the Rural Clinical School of Western Australia (RCSWA) spend one year of clinical study learning in small groups while embedded in rural or remote communities. This aims to increase the locally trained rural medical workforce. Their learning environment, the clinical context of their learning, and their rural doctor-teachers all contrast with the more traditional learning setting in city hospitals. The RCSWA has succeeded in its outcomes for students and in rural medical workforce impact; it has grown from 4 pilot sites to 14 in 12 years. This reflective piece assimilates observations of the formation of the RCSWA pedagogy and of the strategic alignment of education technologies with learning environment and pedagogy over a seven-year period. Internal and external influences, driving change in the RCSWA, were considered from three observer perspectives in a naturalistic setting. Flexibility in both education technologies and organizational governance enabled education management to actively follow pedagogy. Peter Senge’s learning organization (LO) theory was overlaid on the strategies for change response in the RCSWA; these aligned with those of known LOs as well with LO disciplines and the archetypal systems thinking. We contend that the successful RCSWA paradigm is that of an LO.