Yes, he does.
He is constantly aware of every file, folder, and directory in his system. Every time he opens a new window or starts a new tab, he sees the exact same path structure. He knows exactly where each file is located, which directories are active, and what data is stored in each location.
He understands the hierarchy of the operating system, the relationships between different components, and the impact that changes have on the system. He is intimately familiar with the structure of his own digital environment.
He doesn't need to ask questions; he already knows everything about his system. He has full control over the entire file system, from top-level directories to individual files.