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HTTPS ensures that the Web has a base level of privacy and integrity. Security engineers, researchers, and browser vendors have long worked to spread HTTPS to as much of the Web as possible via outreach efforts, developer tools, and browser changes. How much progress have we made toward this goal of widespread HTTPS adoption? We gather metrics to benchmark the status and progress of HTTPS adoption on the Web in 2017. To evaluate HTTPS adoption from a user perspective, we collect large-scale, aggregate user metrics from two major browsers (Google Chrome and Mozilla Firefox). To measure HTTPS adoption from a Web developer perspective, we survey server support for HTTPS among top and long-tail websites. We draw on these metrics to gain insight into the current state of the HTTPS ecosystem.