Facing multiple environmental crises as we currently are, holistically oriented environmental architecture offers promise for (re)thinking and (re)building the way we dwell in space and experience landscapes by attending to sociocultural entanglements in local contexts and thereby moving beyond simple technofixes. As Montanans emphasize a commonly held value of the land by both settlers and indigenous people across the political spectrum, this project explores approaches to environmental design in Montana in conversation with the settler-colonial context of the state and the varying attachments to and understandings of landscape embedded in these design visions. Regionally based environmental architects in Montana usually aim to build for connection, understanding buildings more as mediations towards human-nature reciprocity rather than abstract separations from landscapes. At the same time, Montana’s settler-colonial legacy and continuous celebrations of frontier logics—through emphases on wilderness, refuge, and the state’s “the last best place” motto—demands attending to the contradictions of an environmentalism that is based on indigenous dispossession and emphasizes individualist notions of escape and survival. Both the attachments to particular creations of landscape as well as visions for certain environmental futures highlight processes of continuous extraction and replacement. In this way, frontier logics are built into settler development of space in Montana and environmental design struggles to leave settler-colonial entitlements to land behind. This paper therefore brings out the tensions of environmental design in a settler-colonial context which undermine the potential promise they hold for building alternative futures and suggests directions for the future of holistically oriented environmental design.