A 4-Hour Drive Overhaul

In the task of reorganizing 3,700 files and 446 folders on Google Drive, Claude Cowork's planning and script writing themselves were quite strong. It scanned all the files to create a structural plan, wrote a PowerShell script for moving files, and even logged each move.

The problem wasn't the AI, but the OS/storage layer.

• Files in Google Drive streaming mode appeared as empty stubs locally, so Cowork couldn't access them directly.
• Drive had to be switched to Available offline first, and copied to an actual local folder with robocopy before work could begin.
• The copies were assigned to a different Windows user profile, causing write failures, and folder ownership had to be changed via Security → Advanced.
• There were also ongoing issues where scripts were saved to the virtual layer, got corrupted due to encoding errors, or were mistakenly saved to OneDrive's Desktop.
• The enterprise SharePoint mount couldn't be disconnected through normal settings, requiring even registry edits.

Ultimately, what this case shows is that while AI's file classification and automation capabilities are practically sufficient, actual success depends on how reliably you can handle Google Drive mounting, Windows permissions, and local path handling. If Cowork could write directly to Drive and natively handle OS permission contexts, it has strong potential to become a much more powerful tool.