Business model design needs to encounter increasing and highly dynamic challenges due to counter-caesural environmental changes. Empirical research on strategic sustainability is expected to provide guidance for needed dynamic transformation and sustainability. The reported research builds on a multi-case research of four German wine estates. The cases each represent a specific generic strategic grouping and distinct business models and are thereby suited to analyse sustainability by leaning on the concept of dynamic capabilities. Sustainability was examined as a strategic vehicle for innovation in the wine industry and a nuanced view of dynamic capabilities. Premium strategist turned out to strongly engage and profile in sustainability with aligned dynamic capabilities as a building block to generate premium products. Quality leadership also leverages product quality with comprehensive dynamic capabilities aiming for sustainability by building on size and a professional structure but less on environmental profiling. The price–value strategy approaches sustainability primarily from a market-based and circular economy view. Niche strategist’s dynamic capabilities in the analysed population illustrated an entrepreneurial and effectuation-based approach with specific dynamic capabilities fine-tuned to exploit market opportunities. The multi-case analyses thereby allowed us to identify strategy-specific and business-model-suiting capabilities.