Digital transformation, organizational resilience, and agility are now becoming key to meeting the competitive challenges of modern organizations. It is no surprise that digital transformation and digital technologies have also begun to significantly impact the energy industry, moving towards improving the sector’s profitability and efficiency. However, to move the difficult process of digital transformation in today’s dynamically changing environment, organizations, including those in the energy sector, need to build organizational resilience. Nevertheless, the relationship between digital transformation and organizational resilience has not yet been explained in a satisfactory and sufficient manner. Focusing on the level of digital transformation, and more precisely within the two dimensions of digital maturity, i.e., digital intensity and transformation management intensity, as well as based on the perspective of dynamic capabilities, this study developed a configurational framework and proposed a theoretical model to study the equifinal paths through which digital transformation and dynamic capabilities influence organizational resilience in energy sector companies. Based on a fuzzy set qualitative comparative analysis (fs/QCA) conducted on selected companies in the energy sector, i.e., Polish CHP plants, the relationship among digital transformation, dynamic capabilities, and organizational resilience was investigated. The results show that a high level of organizational resilience is possible to achieve through two main paths based on the dominance of dynamic capabilities and the dominance of digital maturity. The results show that a high level of organizational resilience is possible to achieve through two main paths based on the dominance of dynamic capabilities and the dominance of digital maturity. The study found that digital maturity can significantly influence CHP resilience. Moreover, the transformation management intensity is strongly related to high organizational resilience. The paper concludes by describing theoretical and practical implications, as well as research limitations and prospects for future research.