On September 20, 2021, Apple released iCloud Private Relay (archive), a new capability embedded into iOS 15, iPadOS 15, and macOS Monterey. Its objective is to enhance the privacy and security of Apple users who surf the web in Apple’s Safari browser. This comes as an exciting news to privacy advocates, especially given Apple’s controversial plans for inspecting iCloud photos, a decision that has caused outrage in the privacy community. In this report, we present an early analysis of iClo...