This paper describes some non-technical challenges of utilizing Distributed Energy Resources (DERs) to achieve electrification in remote rural regions that fall outside the reach of the conventional utility grid. These non-technical challenges stem partly from the inability to utilize economies of scale, but are also related to place-based contexts of the communities that these systems are designed to serve. This paper provides some insights from a case study of DER usage for electrification in the Navajo Nation (NN) and the challenges that are involved. It describes through this illustrative case study why technology solutions and long-term policy initiatives and support -explicitly crafted using knowledge of place and people -are necessary to advance electrification goals in rural and under-served communities.