Digital transformation strategies (DTS) are essential for companies that aim to navigate digital disruption and unlock new business opportunities. This study explores why DTS in Mittelstand enterprises (MEs) often fall short on enabling digital business. Using a qualitative multi-case study, we analyze the content and development of DTS in MEs to understand its role in driving digital transformation. Our findings reveal that DTS in MEs predominantly supports traditional business models, with limited emphasis on developing new digital businesses. Entrenched strategy-making of MEs—characterized by a top-down, deliberate approach focused on feasibility and value for the traditional business—constrains the transformation potential of MEs’ DTS. Building on existing DTS research, we conceptualize how DTS manifests in the ME context and highlight the need for new strategic practices that explicitly incorporate digital business goals. Furthermore, we contribute to ongoing discussions on the contextual embeddedness of digital transformation.