Windows Organizer

Windows Organizer

Use when the user wants to clean up a Windows PC, free disk space, reorganize files, or reconcile files that live on both a Windows machine and Google Drive — while converging Windows, macOS, and Drive on one folder layout.

Pairs with mac-organizer (same canonical layout) and google-drive-organizer. To operate a specific remote Windows box over Tailscale SSH (connection details, WSL, runner), see dell-windows-host.

Triggers

• "clean up my Windows PC", "my C: drive is full", "free up space on Windows"
• "organize my Windows Desktop / Downloads / Documents"
• "the same files are on my Windows PC and Google Drive" / "find duplicates between Windows and Drive"
• "make my Windows folders match my Mac"
• "go over these one by one, don't delete anything, compare versions"

Phase 0 — Connect (or run locally)

Run everything below either directly in PowerShell on the box, or over SSH from another machine. For a specific pre-configured host, dell-windows-host has the exact connection recipe — reuse it and skip this phase.

Tailscale gives the network path. It does not log you in. The Windows OpenSSH server still authenticates by key or password. Tailscale SSH's keyless server is Linux-only, so a Windows node falls back to stock OpenSSH.

# from the Mac/Linux side — Windows node reachable on the tailnet
tailscale status                 # find the Windows node name + 100.x IP
tailscale ping <windows-node>
nc -z <ip> 22                    # OpenSSH server up?
ssh -i ~/.ssh/<key> <user>@<ip> "hostname; whoami"

Windows OpenSSH auth gotcha (the usual failure): for a member of the local Administrators group, the public key must go in C:\ProgramData\ssh\administrators_authorized_keys — not the user's ~/.ssh/authorized_keys — and that file needs tight ACLs, or sshd ignores it silently and you get Permission denied (publickey,password,...).

# on the Windows box, once, as admin — authorize a key for an admin user
$k = 'ssh-ed25519 AAAA... comment'
Add-Content C:\ProgramData\ssh\administrators_authorized_keys $k
icacls C:\ProgramData\ssh\administrators_authorized_keys /inheritance:r
icacls C:\ProgramData\ssh\administrators_authorized_keys /grant "Administrators:F" "SYSTEM:F"
Restart-Service sshd

Confirm the exact login username — whoami on the box prints hostname\username; the SSH user is the username part. Do not assume it matches the Mac user.

Run everything below either in an SSH session or directly in PowerShell on the box. Prefer PowerShell (pwsh/powershell) over cmd.

Phase 1 — Disk Space Audit

Get-PSDrive -PSProvider FileSystem | Select Name, @{n='FreeGB';e={[int]($_.Free/1GB)}}, @{n='UsedGB';e={[int](($_.Used)/1GB)}}

# biggest top-level buckets under the profile
$dirs = "$env:USERPROFILE\Desktop","$env:USERPROFILE\Downloads","$env:USERPROFILE\Documents","$env:LOCALAPPDATA","$env:APPDATA"
foreach ($d in $dirs) {
  $gb = [math]::Round((Get-ChildItem $d -Recurse -File -EA SilentlyContinue | Measure-Object Length -Sum).Sum/1GB, 2)
  "{0,8} GB  {1}" -f $gb, $d
}

Find the heavy caches:

Get-ChildItem "$env:USERPROFILE\Documents" -Recurse -Directory -EA SilentlyContinue |
  Where Name -in 'node_modules','.next','.turbo','dist','build' |
  Select FullName, @{n='GB';e={[math]::Round((Get-ChildItem $_.FullName -Recurse -File -EA SilentlyContinue|Measure Length -Sum).Sum/1GB,2)}} |
  Sort GB -Desc | Select -First 15

Phase 2 — Safe Cache Deletions (regenerable, always safe)

These are package-manager and build caches. They rebuild on next install/build.

# npm / yarn / pnpm / bun
npm cache clean --force
Remove-Item "$env:LOCALAPPDATA\npm-cache" -Recurse -Force -EA SilentlyContinue
Remove-Item "$env:LOCALAPPDATA\Yarn\Cache" -Recurse -Force -EA SilentlyContinue
Remove-Item "$env:LOCALAPPDATA\pnpm-store","$env:LOCALAPPDATA\pnpm\store" -Recurse -Force -EA SilentlyContinue
Remove-Item "$env:USERPROFILE\.bun\install\cache" -Recurse -Force -EA SilentlyContinue

# Playwright / Puppeteer browser downloads
Remove-Item "$env:USERPROFILE\AppData\Local\ms-playwright" -Recurse -Force -EA SilentlyContinue
Remove-Item "$env:USERPROFILE\.cache\puppeteer" -Recurse -Force -EA SilentlyContinue

# Windows temp
Remove-Item "$env:TEMP\*" -Recurse -Force -EA SilentlyContinue

# build caches inside repos (never inside node_modules)
Get-ChildItem "$env:USERPROFILE\Documents" -Recurse -Directory -EA SilentlyContinue |
  Where { $_.Name -in '.next','.turbo' -and $_.FullName -notmatch 'node_modules' } |
  ForEach-Object { Remove-Item $_.FullName -Recurse -Force -EA SilentlyContinue }

node_modules are regenerable but slow to rebuild — confirm with the user before mass-deleting them, then reinstall per repo with npm i / pnpm i.

Windows built-in reclaimers (offer, don't auto-run — they need elevation):

cleanmgr /sagerun:1          # Disk Cleanup
Dism.exe /Online /Cleanup-Image /StartComponentCleanup   # WinSxS component store

Phase 3 — File Organization

Canonical structure (same as mac-organizer)

Converge Windows %USERPROFILE%\Documents, macOS ~/Documents, and the Google Drive root on one layout:

Documents/
├── {project}/          # one dir per project/brand (flat, no nesting)
│   ├── code/           # git repos
│   ├── assets/         # logos, brand images
│   ├── docs/           # strategy, specs
│   ├── content/        # marketing, social
│   └── research/
├── {you}/              # your personal "project"
│   ├── immigration/
│   ├── finances/
│   │   ├── invoices/
│   │   └── receipt-photos/
│   ├── health/
│   ├── legal/
│   ├── photos/
│   └── notes/

Desktop / Downloads sort (move, never delete)

$D = "$env:USERPROFILE\Desktop"
New-Item -ItemType Directory -Force "$D\Screenshots","$D\Documents","$D\Installers" | Out-Null

Move-Item "$D\Screenshot*.png" "$D\Screenshots\" -EA SilentlyContinue
Move-Item "$D\*.pdf"           "$D\Documents\"   -EA SilentlyContinue
Move-Item "$D\*.exe","$D\*.msi" "$D\Installers\" -EA SilentlyContinue

Phase 4 — Reconcile Windows vs Google Drive (report-only, no deletes)

The core job when the same files live on the Windows PC and in Google Drive. Never delete. Compare, classify, report. The human decides each action.

Method — hash + modified-time on both sides, match by relative path, classify:

Build the manifest on each side, then diff. Example (Windows side; produce a matching one for the Drive root, then join on Rel):

$root = "$env:USERPROFILE\Documents"
Get-ChildItem $root -Recurse -File -EA SilentlyContinue | ForEach-Object {
  [pscustomobject]@{
    Rel   = $_.FullName.Substring($root.Length).TrimStart('')
    Size  = $_.Length
    MTime = $_.LastWriteTimeUtc.ToString('o')
    Hash  = (Get-FileHash $_.FullName -Algorithm SHA256).Hash
  }
} | Export-Csv "$env:TEMP\windows-manifest.csv" -NoTypeInformation

Then join the two manifests on Rel (in PowerShell, or pull both CSVs to one machine and diff there) and emit the classification table above. Output is a report — a table plus a CSV of every non-identical file. No Remove-Item, no Move-Item in this phase.

Hashing gotchas:

• Google Drive for Desktop streams files. Get-FileHash on a Drive-streamed file forces a download; for a big tree, hash by size first and only hash SHA-256 where sizes match.
• Compare by content hash, never by name or size alone — same name + same size can still differ.
• Normalize path separators (\ vs /) and case before joining, or matches are missed.

After the user reviews the report, apply only the actions they approve — copy up, copy down, or move into the canonical layout. Deletion, if ever, is a separate explicit step the user asks for by name.

Phase 5 — Descriptive File Renaming

Windows has no on-device Apple Intelligence equivalent that's private-by-default. Options, cheapest first:

1. Directory-context naming (no AI, no network): derive a slug from the folder + date + a counter, e.g. invoices\2025-04\shaw-internet-2025-04.pdf. Deterministic, offline, good enough for most sorting.
2. Local OCR for scanned receipts/images via Tesseract (winget install UB-Mannheim.TesseractOCR), then the directory-context slug from the extracted text.
3. Cloud LLM only with explicit user opt-in — never send personal documents to a cloud model without asking.

Prefer 1. Reserve 2–3 for files the folder context can't name.

Guardrails

• Never delete in the reconcile phase. Phase 4 is report-only by design.
• Confirm the SSH username and that you're on the intended host (hostname) before any bulk operation.
• Move-Item before Remove-Item, always — moving into the canonical layout is reversible; deleting is not.
• Dry-run mass moves first: build the list with Get-ChildItem, show it, then act.
• Don't touch C:\Windows, Program Files, or another user's profile.