I’ve come to realise that I wasn’t the only one that has never actually exploited an HTTP Request Smuggling vulnerability, three years after James Kettle reminded the world of it. Like many, I’ve seen the buzz, read it all, thought I understood it, but honestly, I didn’t. While the potential impact sounds great from an attacker perspective, I’ve been mostly confused by a lot of it. That was until the 2022 HackTheBox Business CTF challenge called PhishTale in the web category came around. Focussing less on the overall solving of the challenge and more on the request smuggling, in this post I’ll tell you about my journey of how I finally got to exploit an HTTP desync attack (specifically HTTP2 request smuggling).