While email is the most ubiquitous and interoperable form of online communication today, it was not conceived with strong security guarantees, and the ensuing security enhancements are, by contrast, lacking in both ubiquity and interoperability. This situation motivates our research. We begin by identifying a variety of stakeholders who have an interest in the current email system and in efforts to provide secure solutions. We then use the tussle among stakeholders to explain the evolution of fragmented secure email solutions undertaken by industry, academia, and independent developers. We develop an evaluation framework for proposed or deployed secure email systems and identify how well they meet properties related to security, utility, deployability, and usability. We conclude with a fresh look at the state of secure email and discuss open problems in the area.