file-organizer

name	file-organizer
description	Intelligently organizes your files and folders across your computer by understanding context, finding duplicates, suggesting better structures, and automating cleanup tasks. Reduces cognitive load and keeps your digital workspace tidy without manual effort.

Model routing: Sonnet for implementation; Haiku for verification/scoring; Opus only for explicit architectural decisions.

File Organizer

This skill acts as your personal organization assistant, helping you maintain a clean, logical file structure across your computer without the mental overhead of constant manual organization.

Instructions

When a user requests file organization help:

1. Understand the Scope

   Ask clarifying questions:

   • Which directory needs organization? (Downloads, Documents, entire home folder?)
   • What's the main problem? (Can't find things, duplicates, too messy, no structure?)
   • Any files or folders to avoid? (Current projects, sensitive data?)
   • How aggressively to organize? (Conservative vs. comprehensive cleanup)

2. Analyze Current State

   Review the target directory:

   # Get overview of current structure
   ls -la [target_directory]
   
   # Check file types and sizes
   find [target_directory] -type f -exec file {} \; | head -20
   
   # Identify largest files
   du -sh [target_directory]/* | sort -rh | head -20
   
   # Count file types
   find [target_directory] -type f | sed 's/.*\.//' | sort | uniq -c | sort -rn
   

   Summarize findings: total files and folders, file type breakdown, size distribution, date ranges, and obvious organization issues.

3. Identify Organization Patterns

   Based on the files, determine logical groupings:

   By Type: Documents (PDF, DOCX, TXT), Images (JPG, PNG, SVG), Videos (MP4, MOV), Archives (ZIP, TAR, DMG), Code/Projects, Spreadsheets, Presentations.

   By Purpose: Work vs. Personal, Active vs. Archive, project-specific, reference materials, temporary/scratch files.

   By Date: Current year/month, previous years, very old (archive candidates).

4. Find Duplicates

   When requested, search for duplicates:

   # Find exact duplicates by hash (cross-platform: md5 on macOS, md5sum on Linux)
   find [directory] -type f -exec sh -c 'command -v md5 >/dev/null && md5 "$1" || md5sum "$1"' _ {} \; | sort | uniq -d
   
   # Find files with same name
   find [directory] -type f -exec basename {} \; | sort | uniq -d
   
   # Find similar-sized files (cross-platform: -ls works on both macOS and Linux)
   find [directory] -type f -ls | awk '{print $7, $NF}' | sort -n
   

   For each duplicate set: show all file paths, display sizes and modification dates, recommend which to keep (usually newest or best-named). Always ask for confirmation before deleting.

5. Propose Organization Plan

   Present a clear plan before making changes:

   # Organization Plan for [Directory]
   
   ## Current State
   - X files across Y folders
   - [Size] total
   - File types: [breakdown]
   - Issues: [list problems]
   
   ## Proposed Structure
   
   [Directory]/
   ├── Work/
   │   ├── Projects/
   │   ├── Documents/
   │   └── Archive/
   ├── Personal/
   │   ├── Photos/
   │   ├── Documents/
   │   └── Media/
   └── Downloads/
       ├── To-Sort/
       └── Archive/
   
   ## Changes I'll Make
   
   1. **Create new folders**: [list]
   2. **Move files**:
      - X PDFs → Work/Documents/
      - Y images → Personal/Photos/
      - Z old files → Archive/
   3. **Rename files**: [any renaming patterns]
   4. **Delete**: [duplicates or trash files]
   
   ## Files Needing Your Decision
   
   - [List any files you're unsure about]
   
   Ready to proceed? (yes/no/modify)
   

6. Execute Organization

   After approval, organize systematically:

   # Create folder structure
   mkdir -p "path/to/new/folders"
   
   # Move files with clear logging
   mv "old/path/file.pdf" "new/path/file.pdf"
   

   Rules:

   • Always confirm before deleting anything
   • Log all moves for potential undo
   • Preserve original modification dates
   • Handle filename conflicts gracefully
   • Stop and ask if you encounter unexpected situations

7. Provide Summary and Maintenance Tips

   After organizing:

   # Organization Complete
   
   ## What Changed
   - Created [X] new folders
   - Organized [Y] files
   - Freed [Z] GB by removing duplicates
   - Archived [W] old files
   
   ## New Structure
   [Show the new folder tree]
   
   ## Maintenance Tips
   1. **Weekly**: Sort new downloads
   2. **Monthly**: Review and archive completed projects
   3. **Quarterly**: Check for new duplicates
   4. **Yearly**: Archive old files
   

Examples

Example 1: Organizing Downloads

User: "My Downloads folder is a mess with 500+ files. Help me organize it."

Process:

1. Analyzes Downloads folder
2. Finds patterns: work docs, personal photos, installers, random PDFs
3. Proposes structure:
   • Downloads/
     • Work/
     • Personal/
     • Installers/ (DMG, PKG files)
     • Archive/
     • ToSort/ (things needing decisions)
4. Asks for confirmation
5. Moves files intelligently based on content and names
6. Results: 500 files → 5 organized folders

Example 2: Finding and Removing Duplicates

User: "Find duplicate files in my Documents and help me decide which to keep."

Output:

# Found 23 Sets of Duplicates (156 MB total)

## Duplicate Set 1: "proposal.pdf"
- `/Documents/proposal.pdf` (2.3 MB, modified: 2024-03-15)
- `/Documents/old/proposal.pdf` (2.3 MB, modified: 2024-03-15)
- `/Desktop/proposal.pdf` (2.3 MB, modified: 2024-03-10)

**Recommendation**: Keep `/Documents/proposal.pdf` (most recent in correct location)
Delete the other 2 copies?

[Continue for all duplicates...]

Pro Tips

1. Start Small: Begin with one messy folder (like Downloads) to build trust
2. Regular Maintenance: Run weekly cleanup on Downloads to prevent buildup
3. Archive Aggressively: Move old projects to Archive instead of deleting — you can always delete later, but you can't un-delete

Best Practices

Folder Naming

• Use clear, descriptive names
• Avoid spaces (use hyphens or underscores)
• Be specific: "client-proposals" not "docs"
• Use prefixes for ordering: "01-current", "02-archive"

File Naming

• Include dates: "2024-10-17-meeting-notes.md"
• Be descriptive: "q3-financial-report.xlsx"
• Avoid version numbers in names (use version control instead)
• Remove download artifacts: "document-final-v2 (1).pdf" → "document.pdf"

When to Archive

• Projects not touched in 6+ months
• Completed work that might be referenced later
• Files you're hesitant to delete (archive first, delete later)