cleanup-computer

name	cleanup-computer
description	Interactive file cleanup workflow for organizing Downloads, Desktop, and Documents folders. Goes file-by-file proposing actions like delete, upload to Google Drive, or move to proper location. Use when user says "clean up my computer", "organize my downloads", "help me declutter", "what's in my Downloads", or "file cleanup". Skips receipts (handled by process-receipt skill).

Computer Cleanup Workflow

This skill helps you systematically clean up and organize files in your Downloads, Desktop, and Documents folders. It processes files one-by-one, showing you each file and proposing an appropriate action.

When to Use This Skill

Use this skill when the user requests:

• "Clean up my computer"
• "Organize my downloads"
• "Help me declutter"
• "What's in my Downloads folder?"
• "File cleanup"
• "Go through my files"

Complementary Skills

This skill is designed to work alongside:

• process-receipt: Handles receipts/invoices specifically
• process-invoice: Handles vendor invoices

Important: Skip files that appear to be receipts or invoices - suggest the user run process-receipt for those instead.

Workflow Steps

1. Initialize Cleanup Session

Start by informing the user:

• "I'll help you clean up your files, going through them one by one."
• "We'll start with Downloads, then Desktop, then Documents."
• "For each file, I'll propose an action: delete, upload somewhere, move, or keep."

2. Process Folders in Order

Process folders in this order:

1. ~/Downloads
2. ~/Desktop
3. ~/Documents

For each folder:

find ~/Downloads -maxdepth 1 -type f -print0 | xargs -0 ls -lt 2>/dev/null | head -20

Skip these system/hidden files:

• .DS_Store
• .localized
• Files starting with .

3. For Each File, Analyze and Propose

For each file found:

a. Read/Analyze the File

• For PDFs: Read and summarize content
• For images: View and describe
• For documents: Read and summarize
• For archives (.zip, .dmg): List contents if possible
• For other files: Show file info (size, date, type)

b. Categorize the File Type

Determine what kind of file it is:

• Receipt/Invoice: Skip, suggest process-receipt skill
• Screenshot: Often deletable, but check if contains important info
• Downloaded installer (.dmg, .pkg): Usually deletable after install
• Archive (.zip): Check contents, often intermediate/deletable
• Document (.pdf, .docx): May need to be filed or uploaded
• Image (.jpg, .png): Could be screenshot, photo, or downloaded image
• Code/config files: Might belong in a project folder
• Media (.mp4, .mp3): Could be moved to appropriate location
• Temporary files: Usually deletable

c. Propose an Action

Use AskUserQuestion to present options based on file type:

For likely deletable files (old installers, temp files, duplicates):

Question: "What should we do with [filename]? (Downloaded [date], [size])"
Options:
- "Delete" - Move to trash
- "Keep for now" - Leave in place
- "Tell me more" - Show more details about this file

For documents/files that might need organizing:

Question: "What should we do with [filename]? [Brief summary of content]"
Options:
- "Delete" - Move to trash
- "Upload to Google Drive" - Upload to a Drive folder
- "Move to [suggested folder]" - Move locally
- "Keep in place" - Leave where it is

For receipts/invoices detected:

Question: "[filename] appears to be a receipt/invoice."
Options:
- "Process with receipt skill" - Run process-receipt
- "Skip for now" - Handle later
- "It's not a receipt - continue" - Process as regular file

4. Execute the Chosen Action

Based on user's choice:

Delete

trash "[file_path]"

Confirm: "Moved [filename] to trash."

Upload to Google Drive

Important: Analyze the file content and suggest an appropriate folder based on context.

Step 1: Analyze and Suggest Folder

Before asking the user, determine a suitable folder suggestion based on:

• File content: What is the document about? (e.g., tax document → "Tax Documents 2025", contract → "Contracts", bank statement → "Financial")
• File name clues: Keywords in filename (e.g., "invoice" → skip to receipt skill, "report" → "Work/Reports")
• File type patterns:
  • Legal/contracts → "Legal Documents"
  • Financial statements → "Financial"
  • Work deliverables → "Work/[Project name if detectable]"
  • Personal documents → "Personal"
  • Educational/courses → "Learning"
  • Medical → "Medical Records"

Step 2: Present Smart Options

Question: "Where in Google Drive should I upload [filename]?"
Options:
- "[Suggested Folder]" - Based on analysis: [brief reason why this folder fits]
- "Documents" - General documents folder
- "Let me specify" - Choose a different folder

Example suggestions based on content:

• Tax form PDF → "Tax Documents 2025 - This appears to be a tax-related document"
• Employment contract → "Legal Documents - This looks like a contract"
• Bank statement → "Financial - This is a financial statement"
• Course certificate → "Learning/Certificates - This appears to be a course completion"
• Medical test results → "Medical Records - This contains health information"
• Project proposal → "Work/[Client Name] - This relates to [detected project]"

Step 3: Handle "Let me specify"

If user chooses to specify:

• Ask: "What folder name should I use? (I'll create it if it doesn't exist)"
• Accept free text input
• Search for existing folder or create new one

Step 4: Upload the File

Use gdrive_helper.py to upload (reuse from process-receipt skill):

~/.claude/skills/process-receipt/venv/bin/python3 ~/.claude/skills/process-receipt/gdrive_helper.py upload "[file_path]" "[folder_id]" "[filename]"

Step 5: Cleanup After Upload

After upload succeeds, ask:

Question: "File uploaded successfully to [folder]. Delete local copy?"
Options:
- "Yes, delete local" - Move to trash
- "No, keep local" - Leave the file

Move Locally

mv "[source_path]" "[destination_path]"

Confirm: "Moved [filename] to [destination]."

Keep

Simply move to the next file.

5. Progress Updates

After every 5 files, provide a summary:

• Files processed: X
• Deleted: Y
• Uploaded: Z
• Moved: W
• Kept: K

Ask: "Continue with the next batch of files?"

6. Folder Transition

When finishing a folder:

• Summarize actions taken in that folder
• Ask: "Ready to move on to [next folder]?"

7. Session Complete

When all folders are processed:

• Provide final summary of all actions
• List any files that were uploaded with their Drive links
• Mention if there are still files remaining (deeper in folders)

File Type Decision Guide

Usually Safe to Delete

• .dmg files (installers, especially if old)
• .pkg files (installers)
• Duplicate files (same name with " (1)", " copy")
• Screenshots older than 30 days
• Empty files
• .zip archives that have been extracted
• Temporary files (.tmp, .temp)
• Browser downloads like download.pdf, document (1).pdf

Likely Needs Review

• PDFs (could be important documents)
• Word/Excel documents
• Images that aren't screenshots
• Archives with unknown contents

Suggest Upload

• Important documents (contracts, statements)
• Work-related files
• Files user explicitly wants to keep but clear from computer

Skip / Special Handling

• Receipts/Invoices: Redirect to process-receipt
• Active project files: Leave in place
• System files: Don't touch

Google Drive Folder Mapping

Business Folders

Bold Conjectures - User's LLC for consulting/business work. Use for:

• Business tax documents (1099s, quarterly estimates, business expenses)
• Client contracts and agreements
• Business invoices and payments
• Consulting deliverables
• Business insurance documents

Common Folder Suggestions by Content Type

Content Type	Suggested Folder	Detection Clues
Business tax docs	Bold Conjectures/Tax	1099, quarterly tax, business expense, LLC
Business contracts	Bold Conjectures/Contracts	consulting agreement, SOW, client contract
Business expenses	Bold Conjectures/Expenses	business receipt, reimbursement
Personal tax docs	Tax Documents 2025	W-2, personal 1099, tax return, IRS
Personal contracts	Legal Documents	personal agreement, lease, terms
Bank/Financial	Financial	statement, balance, transaction, bank name
Medical	Medical Records	lab results, prescription, doctor, diagnosis
Work deliverables	Work/[Project]	client names, project keywords
Certificates	Learning/Certificates	certificate, completion, course
Insurance	Insurance	policy, coverage, claim
Property/Real Estate	Real Estate	deed, lease, mortgage, property
Personal ID	Personal/Identity	passport, license, ID

Business vs Personal Detection

When analyzing tax or financial documents, determine if it's business or personal:

• Business (→ Bold Conjectures): 1099-NEC, 1099-MISC, business expenses, client payments, consulting income, LLC documents
• Personal (→ Tax Documents or Financial): W-2, personal bank statements, personal insurance, personal tax returns

Note: This skill reuses the Google Drive helper from process-receipt. Ensure that skill is set up first.

Error Handling

• File in use: Skip and note it, come back later
• Permission denied: Inform user, skip file
• Upload fails: Keep local file, report error
• File not found: May have been moved/deleted, skip
• Folder not found in Drive: Offer to create it or choose alternative

Example Session

User: "Clean up my computer"

Claude: I'll help you clean up your files, going through them one by one.
        Starting with Downloads...

        Found 12 files in ~/Downloads.

        File 1: "Chase-Statement-Nov-2025.pdf" (245 KB, downloaded 3 days ago)
        This appears to be a bank statement from Chase for November 2025.

        [Options presented:]
        - "Upload to Financial" - This is a financial statement
        - "Delete" - Move to trash
        - "Keep in place" - Leave in Downloads

User: [Selects "Upload to Financial"]

Claude: Uploaded to Google Drive → Financial/Chase-Statement-Nov-2025.pdf
        Delete local copy?

        [Options: Yes/No]

User: [Selects "Yes"]

Claude: Done. Moving to next file...

        File 2: "Zoom-installer.dmg" (15 MB, downloaded 2 weeks ago)
        This is an application installer for Zoom.

        [Options presented:]
        - "Delete" - Installer likely no longer needed
        - "Keep for now" - Leave in place

Notes

• ALWAYS use trash instead of rm, rm -rf, or rm -r for ALL deletions — files, directories, caches, everything. This ensures recoverability. The only exceptions are commands that manage their own cleanup (e.g., npm cache clean --force, brew cleanup).
• Always read/analyze file content before suggesting a folder
• The suggested folder should be the first option presented
• Include a brief reason why the folder was suggested
• Learn from user's choices during the session (if they keep picking "Work" for certain file types, prioritize that)
• When uncertain about content, default to "Documents" as the suggestion