Smallholder farmers in Chimanimani District, Zimbabwe, have grappled for a long time with the effects of climate change despite the locally and externally driven resilience-building initiatives in place. This paper adopts a qualitative approach to explore the encountered adaptation barriers. Smallholder farmers, Agricultural Technical and Extension Services (AGRITEX) officers, and the traditional leadership fraternity were randomly selected from the district’s 22 rural wards as study participants. Data were solicited using focus group discussions and face-to-face interviews that were corroborated by researcher observation methods. The data were analysed using thematic content analysis of key perspectives drawn from smallholder farmers, traditional leaders, and extension officers who work with farmers. What was unveiled is an assortment of barrier dynamics related to climate, finance, infrastructure, generational change, water resources, inefficient bureaucracy, gender inequality, and health barriers. Vensim PLE 7.3 software was used to illustrate barrier components as they act together to cripple smallholder farmers’ efforts to raise their adaptive capacity. Adaptation barriers are complex and, therefore, cannot be addressed using policies that are fragmented. The paper recommends a multidimensional approach by policy makers to analyse adaptive barriers to build more climate resilience within smallholder farmer communities.