A detailed walkthrough of the HackTheBox machine 'VariaType', which hosts a Flask-based font generator and a PHP validation portal. The attack chain involves: recovering portal source code from an exposed .git repository to obtain credentials; exploiting a single-pass filter bypass (....// pattern) in a PHP download endpoint for arbitrary file read; leveraging CVE-2025-66034 (arbitrary file write in fontTools varLib) to drop a PHP webshell into the portal's web root; exploiting command injection via malicious archive filenames in an outdated FontForge build triggered by a cron job to pivot users; and finally abusing a sudo-allowed plugin installer using a vulnerable setuptools version with a PackageIndex path traversal to write an SSH key to root's home directory.