Alaska is experiencing some of the highest rates of warming in the world, which is leading to a host of climate-related environmental changes, including permafrost thaw, coastal erosion and sea ice loss. Such changes pose significant risks to infrastructure, food and water security, and transportation, especially for Alaska Native communities dependent on subsistence food harvest. In response, there is increasing interest among Alaska Natives to enhance community resilience through climate adaptation planning. Drawing on these two case studies, this chapter outlines barriers, lessons learned and best practices when collaborating with Alaska Native communities to support climate adaptation planning. The authors’ analysis is based on 15 interviews with community members involved in coastal climate adaptation planning efforts in northwest Alaska (Nome and Shaktoolik) and an archival analysis. Their analysis identifies several barriers to planning and implementation of climate adaptation planning in northwest Alaska, including competing priorities, funding, multi-level governance and coordination. Lessons learned and best practices for supporting climate adaptation planning in rural indigenous communities include respecting tribal sovereignty, building trusted relations, engaging communities, scoping, respecting local/traditional knowledge, supporting capacity building and networking, supporting an integrated approach to address climate risks and a focus on outcomes.