File Management
Organize, rename, classify
28 cases
Cowork Local Sessions Ballooning? He Turned Anthropic Support's Reply Into a Cross-Platform Cleanup Skill →
The author noticed his local Cowork sandbox kept growing and that Archive doesn't actually delete files. His first attempt — letting Claude clean up the 23GB sandbox directly — broke Cowork, and he had to restore it with Codex and Claude CLI. After that he emailed Anthropic support and got the real session-folder path (~/Library/Application Support/Claude/local-agent-mode-sessions/<account>/<org>/ on Mac). Since he runs Windows, he had Claude CLI find the equivalent path, then list every session numbered by title so he could delete selectively. He packaged the whole flow as a /delete-old-cowork skill: cross-platform discovery, metadata-only reads (never transcripts), user-confirmed batch deletion, explicit refusal to touch agent/ or cowork-gb-cache.json — a safe scalpel for anyone hitting the same problem
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
Mac Storage Cleanup: Recovered 60GB of Disk Space →
M2 MacBook Air user (256GB) with 3 years of accumulated files. Cowork scanned Documents, Applications, cache directories, identified unnecessary files, and recovered ~60GB (25%) of storage
Pet Photo Identification and Organization →
Used Cowork to intelligently identify hundreds of pet photos. Identified each pet using reference photos and sorted into correctly labeled folders by pet name
Auto-Rename Photos Based on EXIF Metadata →
Japanese tech media test: Cowork reads photo EXIF timestamps and batch renames to YYYYMMDD_HHMMSS format in under 2 minutes
⚠️ Safety Incident: 15 Years of Family Photos Accidentally Deleted →
DVC founder Nick Davidov asked Cowork to organize his wife's desktop. After requesting permission to delete "temp Microsoft Office files," it accidentally deleted 15 years of family photos
⚠️ Safety Incident: iCloud Sync Bug Caused Permanent Legal Document Loss →
User granted Cowork access to ~/Documents with iCloud "Optimize Mac Storage" enabled. Cowork copied 0-byte placeholder files then deleted originals, causing divorce proceedings, guardianship petitions, and police reports to be permanently deleted via iCloud sync
Batch File Conversion and Compression →
Convert documents to PDF, compress PDFs, and normalize image formats in one batch
Invoice Filename Normalization →
Rename messy invoice PDFs into a consistent date-vendor-subject format
Downloads PDF Content Organization →
Categorize and rename about 300 downloaded PDFs by content and build a new folder structure
Video Footage Auto-Organization →
Automatically categorize footage from SD card by camera position and file type, and prepend date to filenames
AI4Agile Prompt Archive Cleanup →
Convert 142 .textClipping prompt files to Markdown, categorize by use case, and build a master index mapped to course modules
Desktop Screenshot Organization →
Author had Claude organize 611 desktop files (mostly screenshots) accumulated over months, sorted by year and month in 2 minutes
611 Desktop Files Organization →
Auto-organize 611 desktop screenshots into folders by year and month in 2 minutes
Downloads Folder Organization →
Auto-organize messy downloads folder by type and date
Desktop and Downloads Folder Cleanup →
Lydia Hallie used Cowork to organize desktop, clean up downloads, and rename files based on content
Content-Aware Batch File Renaming →
Intelligently batch rename files based on content with consistent naming patterns
Duplicate File Detection and Cleanup →
Scan folders to identify duplicate files, generate cleanup report and safely delete copies
Smart File Search →
Use Claude to quickly find files by content, name, date and more
Duplicate File Finder and Cleaner →
Automatically find and remove duplicate files to free up disk space
Photo Organizer by Date and Location →
Automatically organize photos by shooting date and location using EXIF data
Automated Folder Backup →
Create automated backup scripts for important folders to prevent data loss
Music Library Metadata Organizer →
Batch fix and enhance music file metadata including artist, album, artwork
Project File Archiver →
Archive completed projects, clean temp files, and compress to save space
Disk Usage Analyzer →
Analyze disk usage to find space-hogging files and folders
Folder Sync and Comparison →
Sync files between folders, compare differences, and keep content consistent
Batch Rename Files →
Smart batch file renaming with Cowork - supports rules, content-based, and date-based naming
Organize Downloads Folder →
Use Cowork to automatically organize messy download folders by file type and date