The Australian and German healthcare system share extensive similarities in their financial and administrative structures. Both countries follow a two-tiered system offering both public and private insurance. As Germany adapted the Australian DRG system in 2003 to bill patients according to diagnosis-related case rates, patient treatment and accounting also follow similar practices. Despite their common preconditions in the “offline” setting, the goals and execution of their nationally initiated eHealth solutions show vast differences. While Australia’s platform-based My Health Record offers an opt-in solution for patients and doctors to exchange healthcare data under shared control between patient and service provider, Germany’s Electronic Health Card (EHC) mandatorily includes personal and insurance data that can be further expanded with medical data and electronic health records. Information on the EHC is mainly managed by healthcare providers. The differing approaches are linked to different opportunities and weaknesses. This paper provides a systematic overview of the Australian and German eHealth system and gives suggestions on strategies and challenges from both countries. By conducting a SWOT analysis, both eHealth systems are critically reflected considering supported processes, applied technologies, and user acceptance. We furthermore discuss the impact of the individual systems on current healthcare issues and the success rate of their initial intentions.