Motivated by recent revelations of widespread state eavesdropping of personal communication, many solutions now claim to offer secure and private messaging. This includes both a large number of new projects and many widely adopted tools that have added security features. The intense pressure in the past two years to deliver solutions quickly has resulted in varying threat models, incomplete objectives, dubious security claims, and a lack of broad perspective on the existing cryptographic literature on secure communication. In this paper, we evaluate and systematize current secure messaging solutions and propose an evaluation framework for their security, usability, and ease-of-adoption properties. We consider solutions from academia, but also identify innovative and promising approaches used “in-the-wild” that are not considered by the academic literature. We identify three key challenges and map the design landscape for each: trust establishment, conversation security, and transport privacy. Trust establishment approaches offering strong security and privacy features perform poorly from the usability and adoption perspective, whereas some mixtures of approaches that have not been well studied in the academic literature might provide reasonable trade-offs in practice. In contrast, once trust is established, in most cases conversation security can be achieved without any user involvement in the case of two-party conversations, with conversations between larger groups still wanting for a practical solution. Finally, transport privacy appears to be the most difficult problem to solve without paying significant performance penalties.