Wanted to share my experience using Cowork for a real task — reorganizing 3,700 files across 446 folders in Google Drive. TL;DR: The AI part was flawless. The infrastructure between the AI and your actual filesystem is still rough. What went wrong: - Cowork can't access Google Drive files directly — it only sees your local filesystem. Drive files in streaming mode are empty stubs. Had to set everything to "Available offline" and robocopy to a real local folder first. - Writes failed because the copy ran under a different Windows user profile. Had to dig into Security → Advanced → change folder Owner. - Cowork wrote the reorganization script to a virtual layer, not my actual filesystem. Then encoding errors corrupted it. Then it saved to the wrong Desktop (OneDrive vs local). - Had to edit the Windows registry to remove a corporate SharePoint mount that wouldn't disconnect through normal settings. What worked well: Cowork audited every file, built a complete folder structure proposal, wrote PowerShell scripts to execute the reorganization, and logged every move. The planning and scripting was genuinely impressive — it understood my file context (work docs, personal finance, career files) and categorized accurately.
Reorganizing 3,700 Google Drive Files with Cowork: A 4-Hour Battle Report
Real user report: reorganizing 3,700 files across 446 folders in Google Drive. AI planning was flawless; the OS-level integration (placeholder files, permissions, registry, OneDrive path conflicts) was the real battle
Scenario
User had a years-old Google Drive mess: 3,700 files scattered across 446 folders, mixing work, personal finance, and career documents. Wanted Cowork to audit, categorize, and restructure the entire directory autonomously.
Prompt
Audit every file in my Google Drive mirror folder. Build a proposed folder taxonomy based on content type (work, personal finance, career, etc.). Generate PowerShell scripts to execute the reorganization, logging every move. Show me the plan before running.
Expected Result
**AI part (flawless):** - Audited all 3,700 files and built a complete folder structure proposal - Wrote PowerShell scripts to execute, logged every move - Accurately understood file context (work / finance / career) and categorized correctly **OS integration (rough):** - Drive streaming files showed as 0-byte stubs → had to set "Available offline" and robocopy to local - Writes failed under a different Windows user profile → manually changed folder Owner - Script got written to a virtual layer, hit encoding errors, saved to wrong Desktop (OneDrive vs local) - Corporate SharePoint mount wouldn't disconnect via normal settings → registry edit **Verdict:** Once Cowork can write directly to Drive mounts and handle Windows permission contexts, this becomes a killer feature.