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Introducing technology as a sustainable means of creating, connecting, and collaborating reveals the need to carefully consider subtle aspects of deployment strategies and support in remote regions. In order to comprehensively address both cultural and technical issues for educational infrastructure, we consider two elements to be key: (1) a staged deployment approach, involving both educators and community members, coupled with (2) uniquely designed collaborative integrated development environments (IDEs) to aid constructivism. This paper presents our current experience with these elements in the context of a pilot project for aboriginal communities on the west coast of British Columbia. Currently, these local communities have been working alongside our group for a staged deployment of programs throughout southern Vancouver Island. In our next phase we will be extending this to more remote regions in the north island and coastal regions. By building on a philosophy of community-driven initiatives for technology (C-DIT), we hope to secure community involvement in the development and testing of necessary tool support. These tools specifically target IDEs for the development of programming skills, and support our long term goal to help secondary and post-secondary level students appreciate both the process and the art of programming.