There are significant challenges with the design and related certification of eVTOL (Electric Vertical Take-off and Landing) aircraft. Much of this is driven by the novel aspects and diversity of technical solutions of eVTOL, for example the significantly increased levels of system complexity due to the use of distributed and integrated propulsion and advanced flight control systems. It is perceived that the regulation is lagging behind the development of novel technologies and applications which are rapidly advancing to develop eVTOL. As such, it is clear that aircraft manufacturers and regulators need to work more closely, in effect going on ‘a journey’ together to ensure certification is achievable. In this paper, typical eVTOL aircraft operating scenarios and design architectures are presented as the certification background. These are then considered regarding risks related to eVTOL certification together with their complex technical solutions and subsequent operation. Safety challenges and considerations are discussed for the future certification of eVTOL