Three case studies are presented here to demonstrate some effective professional learning approaches set in remote contexts. Through the use of case studies, this chapter illustrates and discusses how remote workforce training is conducted in the school education sector in remote northern Australia. Workforce training in this chapter is geared towards professional learning required to build the capacity of school leaders located a long way from urban and city locations. Each case study focuses upon the interplay between the quality of professional learning opportunities available to remotely located participants and the use of technologies to support learning in remote locations. Issues emerging from the case studies are discussed, with particular attention paid to the enabling nature of the selected technologies. The chapter concludes by proposing some future directions and potential research activities.