Semi-arid regions are particularly vulnerable to compound climate extremes. To transform a region towards climate resilience, strategies, actors and their narratives are key. Long-term analyses of strategies are rare even though required to trace their evolution, uncover changes in dynamic environments, and guide regional development. We use a qualitative research design to (i) identify regional strategies against droughts and heavy precipitation and reveal their implementation status; (ii) explore the narratives of involved actors for and against regional strategies; and (iii) extract factors that are perceived to enable or impede the development or realization of regional strategies. The theoretical concepts of strategy, actors and narratives have guided our qualitative research in the semi-arid Seewinkel region in Austria. We have conducted and analyzed semi-structured interviews with regional actors from the water management, agriculture and nature conservation sectors in the semi-arid Seewinkel region. Qualitative data analysis revealed nine factors related to strategy, actors and context that enable or impede the development and realization of strategies against climate extremes. For a strategy against climate extremes to succeed in the long-term, we find that key players, broad societal support and actors' emotional responses are equally important than long-term effectiveness, adequate financial resources, and appropriate legal frameworks. Future research could explore the interactions among the identified factors, assess their relevance at critical phases of strategy processes, and compare empirical data across various semi-arid regions to identify universally applicable enabling factors.