Our society increasingly relies on web-based services like online banking, shopping, and socializing. Many of these services heavily depend on secure end-to-end transactions to transfer personal, financial, and other sensitive information. At the core of ensuring secure transactions are the HTTPS protocol and the "trust" relationships between many involved parties, including users, browsers, servers, domain owners, and the third-party Certification Authorities (CAs) that issue certificates binding ownership of public keys with servers and domains. This article presents an overview of the current trust landscape and provides statistics to illustrate and quantify some of the risks facing typical users. Using measurement results obtained through passive monitoring of the HTTPS traffic between a campus network and the Internet, we provide concrete examples and characterize the certificate usage and trust relationships in this complex landscape. By comparing our observations against known vulnerabilities and problems, we highlight and discuss the actual security that typical Internet users (such as the people on campus) experience. Our measurements cover both mobile and stationary users, consider the involved trust relationships, and provide insights into how the HTTPS protocol is used and the weaknesses observed in practice. While the security properties vary significantly between sessions, out of the 232 million HTTPS sessions we observed, more than 25% had weak security properties.