DarkCorp is an Insane-difficulty Windows machine with several computers joined. The initial foothold involves exploiting CVE-2024-42009, an XXS vulnerability and IDOR in RoundCube, via the Contact Page to read emails from a developer and leak a hidden, password-protected Analytics dashboard. By leveraging the XXS vulnerability, a separate vhost is accessed, which is vulnerable to a command injection vulnerability using Postgres, allowing us to gain an initial foothold on the machine. Then, an internal web application monitoring service is abused by relaying the authentication request to the domain controller. Furthermore, PrinterBug is used to coerce the web server within DarkCorp's internal network following a Kerberos relay attack to compromise the host. After enumerating Credential Manager installed in the web server, abusing ACLs using the credentials found, and exploiting "A broken marriage, Abusing mixed vendor Kerberos stacks" to get an SSH session on the Drip machine, finally the cached credentials inside the host is extracted which can be leveraged to manage Group Policy Objects allowing us to add a local administrator account to get adminitrative access to the domain controller.