Agent Skills: Cowork Folder Organizer

Cowork Folder Organizer

Turn a chaotic folder into an organized, navigable workspace the way Claude Cowork works through a directory: inventory everything first, propose before moving, then execute with a full undo trail. Never destroy information -- every move is logged and reversible.

Input

Take a directory path. If none is provided, ask for one. Confirm scope before touching anything: subdirectories included or not, and whether any paths are off-limits.

Workflow

1. Inventory. Walk the directory. For every file record name, extension, size, modified date, and a one-line content summary (read headers/first lines for documents, metadata for media). Do not open files larger than 50MB; classify by name and type only.
2. Classify. Group files into categories inferred from the actual contents -- not a generic template. Typical clusters: active project files, reference material, financial documents, contracts, media/assets, installers and archives, duplicates, junk (temp files, ~$ locks, empty files).
3. Detect duplicates. Match by checksum first, then by near-identical names with version suffixes (final, final2, v3, (1)). Identify the canonical copy (newest complete version) and mark the rest.
4. Propose. Present the target folder tree, the naming convention (default: YYYY-MM-DD-descriptive-name.ext for dated documents, client-project-doctype for client work), the duplicate resolution list, and the junk list. Wait for approval before moving anything.
5. Execute. Create the structure, move and rename files, quarantine duplicates and junk into _review-before-deleting/ -- never delete outright. Log every operation as old-path -> new-path in _organizer-log.md.
6. Index. Write INDEX.md at the root: the new tree, what lives where, and a table of the 20 most recently active files so the owner can re-orient instantly.

Rules

• Propose first, move second. Never reorganize without showing the plan.
• Never delete. Quarantine to _review-before-deleting/ and let the human pull the trigger.
• Preserve anything that looks like the only copy of original work (contracts, signed PDFs, raw footage) in place if its location seems intentional.
• Keep names human-readable. No hash suffixes, no ALL_CAPS, no spaces-to-underscores churn on files that are already well named.
• If the folder is a shared drive, flag files other people may have links to before renaming them.
• Report at the end: files processed, moved, renamed, duplicates found, space reclaimable.

Scheduled Mode

When run as a recurring Cowork scheduled task (e.g. weekly on Downloads), skip the approval step only for previously approved rules: apply the established convention to new files, quarantine new junk, and post a summary of what moved. Anything that does not match an existing rule goes to _needs-decision/ and is listed in the summary.

Quick Commands

• "Organize [path]" -- full workflow with proposal
• "Just show me the plan" -- phases 1-4 only, no changes
• "Dedupe only" -- duplicate detection and quarantine, no restructuring
• "Undo" -- reverse the last run from _organizer-log.md