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Squirrel User Guide

Covers Squirrel v1.3

What's New in v1.3

  • The Stash — after organizing, browse exactly what got sorted in a clean, Finder-style window. Icon, List, and Column views, Quick Look previews, and full keyboard navigation
  • Structure Presets — save your favorite folder structures (date format, Custom Format, Super Mode state) and switch between them with one click, right alongside your saved destinations
  • Smarter Custom Format — literal folder names now resolve exactly as typed, no more unexpected fallbacks to a default date tree
  • The {ROOT} token — an explicit way to tell Squirrel "no date folders at all," instead of leaving the Custom Format field blank
  • Redesigned Output zone — Destination and Structure are now separate, clearly labeled pickers
  • First-run welcome screen — a quick tour the first time you launch Squirrel, revisit it anytime from the Help menu

What Squirrel Does

Squirrel organizes your files automatically. Drop in a folder of photos from a shoot, choose where you want them to go, and Squirrel sorts everything by year, month, and day — reading the actual capture date from your files, not just when they were copied.

Turn on Super Folders, and Squirrel also sorts by file type — RAW here, JPEG there, video wherever you want it — fully organized, fully customizable, no extra effort. Save the setups you use often as presets, and confirm exactly what happened afterward in The Stash.

Getting Started

The first time you launch Squirrel, a short welcome screen walks through the basics. You can revisit it anytime from Help → Re-read First Run.

  1. Launch Squirrel
  2. Drag a folder of files onto the Input zone (left)
  3. Drag your destination folder onto the Output zone (right)
  4. Choose your folder structure (and turn on Super Mode if you want type-based sorting)
  5. Click Organize

That's the whole flow. Everything else is optional.

The Input Zone

The Input zone is where you drop the files you want to organize.

What you can drop in:

  • A single folder
  • Multiple folders at once
  • Folders containing subfolders — Squirrel finds all files recursively

Supported file types: Photos, RAW files (from every major camera manufacturer), video, audio, PDFs, documents, spreadsheets, archives, design files (including Photoshop, Illustrator, Affinity, and Pixelmator Pro), 3D files, eBooks, and project files (Xcode, Logic, Final Cut, Premiere, and more).

Removing files: Click the × button on any file row in the Preview panel to exclude it from the organize run. The file stays in its original location — it's just skipped.

Empty folders: You can drag in an empty folder. It contributes 0 files to the count. The Organize button stays disabled until at least one file is loaded.

The Output Zone

The Output zone now has two clearly labeled sections: Destination (where your files go) and Structure (how they're organized once there). They work independently, so you can mix and match — the same destination with different structures, or the same structure across different destinations.

Destination

  • Choose a saved preset or destination from the picker, or
  • Drag any folder onto the Output zone, or
  • Click to browse and pick a folder from Finder, or
  • Press ⌘O to open the folder picker

Select None — Choose a Folder from the picker at any time to clear the current destination.

What you can use as a destination:

  • Any folder on your Mac
  • An external drive or SSD
  • The root of a mounted drive (drag the drive icon directly)

Read-only destinations: If you drop a read-only folder or drive, Squirrel shows an error with an × button. Clear it and choose a writable location.

Deleted destinations: If the destination folder is deleted while it's set, Squirrel detects this when you click Organize and shows the error state.

Structure

Choose None — Use Preferences Default to organize using whatever is currently set in Preferences → Super Folders, or select a saved Structure Preset to apply a specific saved configuration for this run only.

When a Structure Preset is active, the Format dropdown below locks to show that preset's format — this is expected, and just means the preset is fully controlling the structure for this run. Your own Preferences settings are never changed by selecting a preset; switch back to None at any time to return to manual control.

Choose Create New Structure Preset... to jump straight to Preferences → Super Folders and build a new one.

The Folders Tab

Open Preferences (⌘,) and click the Folders tab (or Super Folders, if Super Mode is on). This is where you control how Squirrel names and structures the folders it creates — for both date sorting and, if you turn it on, type sorting.

Built-in formats:

  • Year / Month / Day — 2026/06/28/ (recommended for most workflows)
  • Year / Month — 2026/06/
  • Year — 2026/

Custom format: Choose Custom to build your own structure using format tokens. See Custom Format & the {ROOT} Token below for full details.

Custom Format & the {ROOT} Token

Available tokens:

  • {YYYY} — 4-digit year (2026)
  • {YY} — 2-digit year (26)
  • {MM} — month, formatted according to your Month Format preference (06, June, or Jun)
  • {DD} — day (28)
  • {ROOT} — no date folders at all (see below)

Click to insert: Below the field, click any token chip to add it to the end of your format — no need to type curly braces by hand.

Building your structure: Use / between tokens to create nested folders, the same way the built-in formats do. Use - or _ to separate tokens within a single folder name.

Example — nested folders: {YYYY}/{MM}/{DD} creates 2026/06/28/

Example — single folder name: {YYYY}-{MM}-{DD} creates 2026-06-28/

Literal text works too: You don't need any tokens at all. A Custom Format of client-work creates a single folder called client-work/ — Squirrel always respects exactly what you type.

Important: Tokens must be uppercase. {yyyy} will not work — type {YYYY}, or use the token chips to avoid the issue entirely.

What's not allowed: A bare / on its own, a leading slash, or two slashes in a row are all treated as invalid and Squirrel will show an error rather than guess what you meant. If you're trying to organize with no date folders at all, use {ROOT} instead — see below.

The {ROOT} Token

{ROOT} is a special token for one specific case: you want no date folders whatsoever, with files landing directly in your destination (or directly into type folders, if Super Mode is on).

  • Click the {ROOT} chip to set it — this clears the field and replaces it with {ROOT} alone.
  • {ROOT} can only be used by itself. While it's active, the other token chips grey out, since combining {ROOT} with a date token wouldn't make sense.
  • If Super Mode is off, files land directly in your Output destination.
  • If Super Mode is on, files land in type folders directly under your Output destination — no date nesting at all.

Example: Destination is DesktopClean, Structure is {ROOT}, Super Mode is on → results in DesktopClean/RAW/, DesktopClean/Photo / Image/, and so on, with zero date folders.

Super Folders

Turn on Super Mode at the top of the Folders tab, and it becomes the Super Folders tab — right there in the tab bar, so you always know at a glance whether it's on.

The first time you turn it on, Squirrel shows a quick dialog explaining what's about to change. You can switch back to Normal Mode anytime, and the dialog won't bother you again if you check "Don't show this again."

What Super Mode does

Once it's on, Squirrel sorts your files by type as well as date. A type folder is automatically appended after your date structure — no configuration needed, though everything about it is customizable if you want more control.

Without Super Folders:
2026/06/28/
  IMG_001.ARW
  IMG_001.jpg
  clip_001.mov

With Super Folders:
2026/06/28/
  RAW/
    IMG_001.ARW
  Photo / Image/
    IMG_001.jpg
  Video/
    clip_001.mov

The two-column layout

With Super Mode on, the tab expands into two columns:

  • Categories (left) — manage which file types belong to which folder
  • Folder Structure (right) — the same date/format controls from the Folders tab, plus Live Preview showing your combined result (date structure + type folder), and a Save Current Structure... button at the bottom to save this configuration as a Structure Preset

Categories, out of the box

Squirrel starts you off with 14 built-in categories covering the file types photographers, video editors, and designers actually use — RAW, Photo/Image, Illustration, Design, Desktop Publishing, Documents, 3D, eBooks, Video, Video Projects, Audio, Audio Projects, Archives, and Code/Development. Any file type Squirrel doesn't recognize falls into Uncategorized rather than getting lost.

Every category is yours to change.

Renaming a category: Double-click its name, type a new one, and press Enter (or just click elsewhere — it saves either way). Press Escape if you change your mind mid-edit.

Adding a file type Squirrel already knows: Click the ••• menu on a category's header and choose to add a file type. Search for it by name.

Adding a file type Squirrel doesn't know: Type it directly in that same search field — no leading dot needed, .psd and psd both work the same. It's added to that category right away, and the dialog stays open so you can keep adding more.

Moving or removing a file type: Tap any file type chip. A small menu lets you move it to a different category or remove it entirely.

Creating a new category: Click + Add at the top of the Categories column and give it a name.

Deleting a category: Click the − next to a category. If it has more than one file type in it, Squirrel confirms before deleting — everything in it falls back to Uncategorized, nothing is lost.

Reordering categories: Use the ••• menu on any category to move it up or down in the list.

Everything you customize — renames, new categories, moved file types — is remembered across restarts. Any custom file type you add stays on your Mac. It's never sent anywhere.

Structure Presets

Structure Presets save a complete folder-structure configuration — date format or Custom Format string, Month Format, and Super Mode on/off — under a name, so you can switch between different workflows in one click without reconfiguring the Folders tab every time.

What's saved in a preset: structure/format, Custom Format string (including {ROOT}, if used), Month Format (captured at the moment you save — editing your global Month Format later won't change existing presets), and Super Mode state.

What's not saved: category customizations. Categories are always global and shared across every preset.

Saving a preset:

  1. Build the structure you want in Preferences → Super Folders
  2. Click Save Current Structure... at the bottom of the tab (or from the Output zone's Structure picker, or from Preferences → Presets)
  3. Check the live preview, give it a name, and save

Using a preset: Select it from the Structure picker in the Output zone. It applies to your current organize run only — your own Preferences → Super Folders settings are left untouched, so you can always switch back to None — Use Preferences Default to return to your manual configuration.

Managing presets: Go to Preferences → Presets to edit, rename, or delete a Structure Preset. Editing reopens the same structure editor you used to create it, pre-filled with its saved values.

Running Organize

Once files are loaded and a destination is set, the Preview panel shows exactly where every file will go — including type folders, if Super Mode is on.

Type-level folders in the preview start collapsed to keep things tidy on larger batches — click to expand any of them.

Review the preview. If everything looks right, click Organize.

Copy vs Move:

  • Copy — files are duplicated at the destination. Originals stay where they are.
  • Move — files are moved to the destination. Originals are removed.

Use Copy when you want to preserve your originals. Use Move when you're done with the source and want to clean up.

Warnings

Squirrel catches problems before they become mistakes. Warnings appear in the panel below the Preview.

Duplicate Files

A duplicate warning means a file with the same name already exists at the destination — including, with Super Folders on, two files that would land in the same type folder even though they came from different dates.

For each duplicate, choose:

  • Skip — don't copy or move this file. Leave it as-is.
  • Overwrite — replace the existing file at the destination.
  • Rename — copy the file with a _1 suffix (for example, IMG_001_1.jpg).

Use Apply to all to set the same resolution for all duplicates at once.

Suspicious Dates

A suspicious date warning means Squirrel detected an unusual date — either very old (before 2000) or in the future.

  • Continue — organize the file using the suspicious date as-is.
  • Skip — exclude the file from this organize run.

Disk Space

If the total size of your files exceeds the available space at the destination, Squirrel warns you before organizing.

Remove large files from the input (click × on their row) until the warning clears, then organize.

The Completion Card

After organizing, the Completion Card shows what happened.

  • Green checkmark — files were organized successfully
  • Amber warning — all files were skipped (usually because they already exist at the destination)
  • Shows file count, total size, and operation (copied or moved)

Click Dismiss to close the card. Your input clears, your output destination stays set — ready for the next batch.

The Stash

The Stash is a read-only browser that shows you exactly what got organized after a run — a Finder-style window mirroring the destination folder structure that was just produced, whatever combination of date folders, type folders, or {ROOT} was used.

The Stash is a browser, not a file manager — it doesn't rename, move, or delete anything. Use it to confirm a run went where you expected, then hand off to Finder for anything else.

Opening The Stash:

  • Automatically after a successful organize run, if enabled in Preferences → General
  • On demand anytime via View → Open The Stash, or its keyboard shortcut
  • Always shows the most recent successful run — running organize again while The Stash is open replaces its contents and brings it forward automatically

View modes: Icon, List, and Column, switchable using the icon buttons at the top of the window.

  • Icon — adjustable icon size, drill into folders by double-clicking
  • List — expandable outline with disclosure triangles, shows size, kind, and modified date
  • Column — Finder-style side-by-side columns; select a file to see a live preview — including an actual image preview for photos — plus its size, kind, dimensions, and modified date in the rightmost column

Navigating:

  • Double-click a folder to open it, double-click a file to open it in its default app
  • Right-click any item for Reveal in Finder
  • ⌘-click or Shift-click to select multiple items
  • Use the search field to filter visible files and folders
  • Arrow keys move selection and drill in/out of folders in List and Column view
  • Select a file and press Spacebar for a Quick Look preview
  • Use the size slider at the bottom of the window to adjust icon size, row height, or column width, depending on the current view

Turning it on or off: In Preferences → General, toggle Show The Stash after organizing.

Destination Presets

Save your most-used output folders as presets so you don't have to drag them in every time.

Saving a preset:

  1. Set your output destination
  2. Click Save as Preset below the Output zone
  3. Give it a name (for example, "Jones Wedding", "Client SSD", or "Archive Drive")
  4. The preset is saved and appears in the picker

Using a preset: Select it from the Destination picker in the Output zone. The destination loads immediately. Select None — Choose a Folder to clear it.

Managing presets: Go to Preferences → Presets to rename, reorder, add new destinations, or delete presets. Presets you add here appear in the main window immediately, and vice versa.

Preferences

Open Preferences with ⌘, or from the Squirrel menu.

General

  • Default Operation — set Copy or Move as your default
  • Default Conflict Resolution — what Squirrel does with duplicates by default (Skip, Overwrite, or Rename)
  • Appearance — System, Light, or Dark mode
  • The Stash — turn automatic opening on or off after each organize run
  • Reset All Data — clears all activity history, presets, saved destinations, categories, and preferences. Returns Squirrel to its original state.

Folders / Super Folders

See The Folders Tab, Custom Format & the {ROOT} Token, and Super Folders above. This one tab handles date structure, Custom Format, and, once Super Mode is on, type categories.

Presets

Manage your saved destination presets and Structure Presets. See Destination Presets and Structure Presets above.

Keyboard Shortcuts

Shortcut Action
⌘R Reset
⌘↩ Organize
⌘, Open Preferences
⌘⇧A Open Activity window
⌘⇧S Open The Stash
⌘⇧L Export diagnostic log
⌘O Open folder picker for output
Escape Dismiss completion card
Spacebar Quick Look preview (in The Stash)
Arrow keys Navigate folders/selection (in The Stash)

Activity Window

Open the Activity window with ⌘⇧A, or from View → Open Activity Window, to see a log of every organize run.

Each entry shows the date, number of files, total size, and operation. Click an entry to expand and see per-file detail.

Getting Help

If you'd like a refresher on the basics anytime, choose Help → Re-read First Run to see the welcome screen again.