A few months ago, I embarked on a security bug hunt within the scope of a private program available through the Intigriti platform. During this endeavor, I encountered an intriguing anomaly while analyzing the redirect from HTTP to HTTPS traffic on a particular host. In this write-up, I will delve into the short journey that started after uncovering this strange behavior, ultimately leading to the discovery of a Client-Side Desync vulnerability within one of Microsoft Azure’s CDN solutions known as Front Door.