Cowork-style cleanup of a messy folder or shared drive -- classifies every file, proposes a target structure, renames to a consistent convention, deduplicates, and writes an index.
SkillScore82Maintained
Automatic
◆Knowledge Management pack
Last verified 8/27/2026
What it changes
Passed 18 of 22 test cases with the skill, and 11 of 22 without it.
Without skill50%
With skill82%
Checks it passed that the model alone missed
Refuses to open content bodies of files larger than 50MB.
Lists unmatched files in the posted execution summary report.
Preserves the original signed contract in its current location.
and 8 more in the full report
7 fixed11 passed either way4 still failing0 broke
Pass-rate lift
+32 pp
Tokens
+6%
Agent turns
0%
Response time
-32%
Model gemini-3.6-flashMeasured 8/27/2026v118 of 22 cases passed with skill
Tokens, turns and time describe resource use, not a dollar price.
See it in action
One of 7 test cases the skill fixed. Same model, same prompt, with and without the skill.
1 of 7
Prompt
My Downloads folder (`~/Downloads`) has gotten completely out of hand with hundreds of random documents, media files, and installers. Could you scan through everything, group the files logically based on their actual content, and give me a clean proposed folder layout to review before you actually move or rename any files?
What was checked, without and with the skill
Checked
Without skill
With skill
Asks whether subdirectories are included in the scan scope before inspecting files.
Missed
Passed
Asks whether any specific subfolders or paths are off-limits before inspecting files.
Missed
Passed
case-01 · gemini-3.6-flash · 8/27/2026 · answers are capped and redacted
What's inside
The instructions your model reads when the skill loads.
SKILL.md36 linessingle file
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