This article focuses on the challenges of teachers at vocational schools with regard to the process of digitalisation in school development during the COVID-19 pandemic. Besides the intrapersonal prerequisites for teaching with technology and the change in learning and teaching attitudes, preconditions concerning schools as part of a learning organisation are examined. A qualitative interview study including N = 18 participants was conducted to identify challenges for teachers, the role of school leadership, and cooperation between stakeholders. The main coping strategies proved to be a clear agenda by the school leadership in connection with reliable technological infrastructure and teachers' willingness to use digital teaching methods.