The digital transformation of the working world has been bringing profound impacts on German vocational education and training (VET). This study analyzes the challenges that German VET is experiencing in the context of digitalization as well as the strategies to overcome these challenges. Based on the concept of sustainable cooperation between vocational schools and companies, this study proposed a theoretical framework for preserving the sustainability of VET in the digital era from three dimensions: the capability of industrial service, attractiveness, and adaptability. Meanwhile, through the content analysis method applied to the study of official research and statistical reports, policy documents, journal articles, etc., three key challenges for German VET are found: the insufficient service capacity of German VET for industrial digitalization, the decreasing attractiveness of VET, and the low level of application of digital competencies. German federal agencies have developed multiple strategies in response, including (1) strengthening the capability of training digital talents through the modernization of the training regulations and framework curricula in 2021; (2) reshaping VET as a more promising track for individuals via information support and expanding development pathways; (3) enhancing the willingness to participate in and the capacity to provide vocational training of companies through financial measures; (4) promoting the digital transformation of VET through the financial support of projects and development of practical assistance.