This chapter provides an overview of Germany’s digital health evolution, tracing key legislative milestones, technological advances, and cultural barriers that shape its current transformation. While initiatives such as the E-Health Act, the telematics infrastructure, the electronic patient record, and DiGA have expanded digital capabilities, adoption remains uneven due to fragmented governance, privacy concerns, and limited public trust. The chapter distinguishes between basic digitization and genuine digital transformation, illustrated by examples such as remote patient monitoring and AI-supported triage. The COVID-19 pandemic acted as a major catalyst, rapidly accelerating telemedicine uptake and regulatory change. Persistent challenges, including interoperability, data governance, and digital literacy, must be addressed to fully realize a resilient, patient-centered digital health ecosystem in Germany.