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In Hack The Box's Cyber Apocalypse event, I tackled the Passman challenge—a web-based task to steal a password from an insecure site. After analyzing the app and discovering a peculiar password-generating function, I turned to Chat GPT-4 for help. Although GPT-4's ethical safeguards initially hindered my efforts, I used Jailbreak Chat to bypass these restrictions and "trick" the AI into assisting me. With GPT-4's help, I brute-forced the admin's password, accessed the account, and obtained the challenge flag. Chat GPT-4's potential in cybersecurity is immense, and it's poised to become a go-to tool for enthusiasts.