Hack The Box: WhiteRabbit Machine Walkthough – Insane Difficulity

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Initial access was achieved through exposed monitoring and documentation services, which leaked internal service names and an unauthenticated workflow configuration. This disclosure revealed sensitive secrets, a vulnerable webhook parameter, and ultimately credentials for a backup system. Abuse of misconfigured backup tooling and sudo privileges allowed extraction of private SSH keys, enabling lateral movement across multiple user accounts and retrieval of the user flag.

Privilege escalation to root involved reverse-engineering a custom SUID binary. Analysis exposed a predictable pseudorandom password generator caused by unsafe seeding logic and an integer overflow, significantly reducing entropy. Recreating the binary locally and brute-forcing the constrained seed space yielded valid credentials, granting SSH access to a privileged user with unrestricted sudo rights and full system compromise.

This machine was a strong example of how exposed internal tooling, poor secret handling, and flawed custom binaries can combine into a complete attack chain.

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