What This Skill Does (and Doesn't)

YES: Organize existing files, find duplicates, analyze disk usage, batch rename/move, clean up clutter NO: Open files, create files/folders, copy files, extract archives, basic file browsing — use standard file operations for those

This is a power tool for reorganization, not a replacement for basic file commands.

Path Security (Non-Negotiable)

• Canonicalize ALL paths before any operation: resolve .., ~, symlinks, then validate
• After canonicalization, reject if path is outside user's home or explicitly allowed directories
• NEVER follow symlinks during traversal — report them as "symlink to X, skipped" and let user decide
• Block these paths absolutely: /, /etc, /var, /usr, /System, /Library, C:\Windows, C:\Program Files
• Paths containing .. after canonicalization = reject with explanation

Fast Path vs Safe Path

Fast path (1-9 files): Execute immediately with brief confirmation: "Move 3 files to Archive? [Y/n]" Safe path (10+ files): Create manifest, show summary, require explicit "yes" or review

This prevents confirmation fatigue for simple operations while protecting bulk actions.

Trash Handling

• Use the operating system's native trash: trash CLI on macOS/Linux, Recycle Bin API on Windows
• If OS trash unavailable, move to ~/.local/share/file-organizer-trash/ with metadata sidecar
• Metadata sidecar (JSON): original path, deletion timestamp, operation ID — NOT path-in-filename
• Never permanently delete without explicit "permanently delete" or "empty trash" command

Undo System

• Every operation creates an undo record in ~/.local/share/file-organizer/undo/TIMESTAMP.json
• Record contains: operation type, source paths, destination paths, checksums of moved files
• "Undo last" reverses the most recent operation using the record
• Undo records expire after 30 days — warn user before expiry
• NO shell scripts for undo — JSON metadata only, executed by the agent

Symlink Policy

• During directory traversal: skip symlinks, report them separately
• "This folder contains 12 symlinks pointing outside — review before proceeding?"
• Never follow symlinks automatically — they're a classic attack vector
• User can explicitly request "follow symlinks" but must confirm each external target

Duplicate Detection (Scalable)

• Phase 1: Group by exact size (instant, no I/O)
• Phase 2: Hash first 4KB of same-size files (fast filter)
• Phase 3: Full hash only for files matching phase 2
• For >10,000 files, require confirmation: "This will take ~15 minutes. Proceed?"
• Cache hashes in ~/.local/share/file-organizer/hash-cache.db (SQLite) with mtime invalidation

Bulk Operations

• Batch rename: Preview ALL transformations if <50 files, first/last 10 if more, always show total count
• Batch move: Verify destination has space before starting, atomic per-file with rollback on error
• Progress: Update every 5% or 30 seconds, whichever is less frequent — not per-file spam
• Error handling: On ANY error, stop, report what succeeded/failed, offer "continue skipping errors" or "rollback completed"

Organization Proposals

• Analyze directory contents FIRST, then propose: "80% images, 15% videos, 5% docs — organize by date or type?"
• Always show concrete examples: "vacation-photo.jpg → 2024/06-June/vacation-photo.jpg"
• Preserve original filenames unless user requests rename pattern
• Create .file-organizer-manifest.json in destination documenting the reorganization for future reference

Size Analysis

• Top consumers by directory, not individual files — users think in folders
• Flag known safe-to-delete: node_modules, pycache, .gradle, build/, target/, Pods/
• Calculate actual vs apparent size (sparse files, hardlinks)
• For cleanup suggestions, always state recoverability: "Deleting node_modules: fully recoverable with npm install"

Platform Specifics

• macOS: Respect .app bundles (they're directories), use trash via Homebrew if available
• Windows: Use long path prefix \\?\ for paths >260 chars, use shell API for Recycle Bin
• Linux: XDG trash spec (~/.local/share/Trash/), handle different filesystem capabilities

Limits and Failures

• Refuse operations on >100,000 files without explicit override: "This affects 250K files. Type 'I understand' to proceed"
• If manifest would exceed 10MB, paginate: "Showing batch 1 of 15 (page through with 'next')"
• Network drives: detect by response time, warn about reliability, suggest local copy first
• Disk full: check before starting, reserve 1% headroom, fail gracefully with partial completion report