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

• 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.
• 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).
• 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.
• 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.
• 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.
• 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