Agent-ready instruction sets for cleaning up Documents and Downloads folders after a Mac-to-Mac migration. Built in Claude.ai on April 6, 2026. These prompts are designed to be fed directly to a Claude Cowork agent or any file-management AI agent.
Canvass my Documents folder and organize it. Here's exactly what I need:
Step 1: Full inventory. Scan ~/Documents recursively. Log every file with its path, size, file type, and last modified date. Output the inventory as a markdown file I can review.
Step 2: Identify and segregate duplicates. Find duplicate files by content hash. Move all duplicates into ~/Documents/_Duplicates_Review/, mirroring the original directory tree inside the review folder to prevent filename collisions. Keep the original in place; move the copy. Log which file was kept and which was moved.
Step 3: Poorly named files. Flag files with generic or meaningless names (e.g., "Untitled," numbered copies like "report (1).docx" or "image (3).png," UUID-style filenames, names that are just numbers). Move them into ~/Documents/_Needs_Renaming/, mirroring the source directory tree. Log where each file came from.
Step 4: Zip files and application artifacts. Move .zip, .dmg, .pkg, .app, and any installer or archive files into ~/Documents/_Archives_and_Installers/. Also catch leftover migration artifacts: .DS_Store clusters, .localized files, empty folders, and broken aliases/symlinks. Log those separately.
Step 5: Deliver a summary report. One markdown file with:
- Total file count and size
- Count and list of duplicates moved
- Count and list of poorly named files moved
- Count and list of archives/installers moved
- Count of empty folders, broken symlinks, or other cleanup candidates
- Any files that look suspicious or out of place (e.g., system files that shouldn't be in Documents)
Rules:
- Do not delete anything. Only move into the review folders.
- Mirror the original directory tree inside each review folder to prevent collisions and preserve traceability.
- If a folder becomes empty after moves, flag it but don't delete it yet.
- Work silently through the scan. Don't narrate each file; just give me the final report.
Canvass my Downloads folder and organize it. Here's exactly what I need:
Step 1: Full inventory. Scan ~/Downloads recursively. Log every file with its path, size, file type, and last modified date. Output the inventory as a markdown file.
Step 2: Identify and segregate duplicates. Find duplicate files by content hash. Move all duplicates into ~/Downloads/_Duplicates_Review/, mirroring the original directory tree inside the review folder to prevent filename collisions. Keep the original in place; move the copy. Log which file was kept and which was moved.
Step 3: Poorly named files. Flag files with generic or meaningless names: "Untitled," numbered copies like "report (1).docx" or "image (3).png," UUID-style filenames, names that are just timestamps or random strings. Move them into ~/Downloads/_Needs_Renaming/, mirroring the source directory tree. Log where each file came from.
Step 4: Categorize by file type. Create these folders and sort remaining files into them:
- ~/Downloads/_Sorted/Documents/ (.pdf, .docx, .doc, .xlsx, .csv, .txt, .md, .pptx)
- ~/Downloads/_Sorted/Images/ (.jpg, .jpeg, .png, .gif, .webp, .svg, .heic, .tiff)
- ~/Downloads/_Sorted/Audio_Video/ (.mp3, .mp4, .mov, .wav, .m4a, .avi, .mkv)
- ~/Downloads/_Sorted/Archives/ (.zip, .dmg, .pkg, .tar, .gz, .rar, .7z)
- ~/Downloads/_Sorted/Installers/ (.app, .dmg, .pkg, .exe, .msi)
- ~/Downloads/_Sorted/Code_and_Data/ (.json, .xml, .html, .css, .js, .py, .sql, .yml)
- ~/Downloads/_Sorted/Other/ (anything that doesn't fit the above)
If a file already landed in a review folder from Steps 2 or 3, don't sort it again.
Step 5: Flag large files. Anything over 100MB gets logged separately with filename, size, and file type so I can decide whether to keep it.
Step 6: Clean up artifacts. Flag .DS_Store files, .localized files, empty folders, broken aliases/symlinks, incomplete downloads (.crdownload, .part, .download), and browser temp files. Move these into ~/Downloads/_Cleanup_Candidates/, mirroring the source tree.
Step 7: Deliver a summary report. One markdown file with:
- Total file count and total size
- Count and list of duplicates moved
- Count and list of poorly named files moved
- Breakdown of sorted files by category with count and total size per category
- List of large files (100MB+)
- Count and list of cleanup candidates
- Any files that look suspicious or out of place
Rules:
- Do not delete anything. Only move or sort.
- Mirror the original directory tree inside every review folder to prevent collisions and preserve traceability.
- If a folder becomes empty after moves, flag it but don't delete it.
- Process Steps 2 and 3 before Step 4 so review folders get priority over sorting.
- Work silently through the scan. Don't narrate each file; just give me the final report.