Many of the benefits we derive from the Internet require trust in the authenticity of HTTPS connections. Unfortunately, the public key certification ecosystem that underwrites this trust has failed us on numerous occasions. Towards an exploration of the root causes we present an update to the common knowledge about the Certificate Authority (CA) ecosystem. Based on our findings the certificate ecosystem currently undergoes a drastic transformation. Big steps towards ubiquitous encryption were made, however, on the expense of trust for authentication of communication partners. Furthermore we describe systemic problems rooted in misaligned incentives between players in the ecosystem. We depict that proposed security extensions do not correctly realign these incentives. As such we argue that it is worth considering alternative methods of authentication. As a first step in this direction we propose an insurance-based mechanism and we demonstrate that it is technically feasible.