Fortune was a tough puppy to crack, it requires good enumeration skills and web exploitation to abuse weak input validation. Knowing how SSL and certificates work made it much more achievable.
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Recently the Qualys Research Team did an amazing job discovering a Heap overflow vulnerability in Sudo. In the next sections, we will analyze the bug and we will write an exploit to gain root privileges on Debain 10.
Rope2 by R4J has been my favorite box on HackTheBox by far. It wasn’t really related to pentesting, but was an immersive exploit dev experience