Context appropriate adaptation interventions and strategies that respond directly to localized climate change stressors, hazards, and vulnerabilities are critical for the sustainable development of countries like Zambia. This chapter examines both localized and systemic climate change risk pathways and barriers to adaptation action in Zambia.A three-staged methodology was applied, combining content analysis, focus group discussions, and expert interviews. Livelihood diversification was identified as the central adaptation option across Zambia, despite little empirical research detailing possible risks of diversification. The dominant adaptation discourse is focused specifically on diversifying within agriculture-based livelihoods. However, as all agricultural activities are impacted by climate change, diversification also needs to be explored in value-added or alternative sectors. With this, a weak policy framework and enabling environment are exacerbating cycles of poverty that underpin climate change vulnerability in Zambia. Moreover, maladaptation risks of existing diversification interventions are high as generic approaches often do not provide suitable options to complex and localized risk profiles.To implement a sustainable transition toward climate resilient and compatible development in Zambia, the authors recommend that a systematic livelihood diversification strategy should be rolled out and future research programs designed to support this. Specifically, this necessitates a system-wide analysis of pre-identified livelihood diversification pathways that can be adapted to different scenarios given the current and future climate uncertainties at local scales. The approach should focus on harnessing the positive feedback loops for systematic change to build resilience, while minimizing the dominant risk pathways and eliminating persistent barriers that enable positive feedback loops driving vulnerability to climate change. Thorough stakeholder engagement and incremental development of diversification options, incentives, penalties, and other governance and/or policy mechanisms will be needed to support these processes.