Squirrel User Guide

Covers Squirrel v1.5

What's New in v1.5

A rebuilt Stash. A sidebar by year and month, Icon, List and Column views, a preview panel with camera and video details, and search across everything in the run. After you organize, it opens on the first file you filed
Liquid Glass. Squirrel now uses the native look of macOS 26, in Light and Dark. Squirrel 1.5 requires macOS 26 or later
The Inspector. Operation, Format, Destination, Structure, Result and Summary now live together in a panel on the right of the main window
A redesigned Activity window. Runs are grouped by day, with search and a filter for Success, Partial and Failed
Stop with ⌘↩. While Squirrel is organizing, the same shortcut that starts a run stops it
Clear buttons. Remove what is in the Input or Output card with one click
One window. Squirrel is a single-window app. ⌘N no longer opens a second window
Reset All Data starts you over. After a reset, the Welcome screen appears again

Your presets, categories, saved destinations and activity history carry over unchanged.

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. It reads 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. 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 see it again anytime from Help → Re-read First Run.

Launch Squirrel
Drag a folder of files onto the Input card
Drag your destination folder onto the Output card
Choose your folder structure in the Inspector (and turn on Super Mode if you want type-based sorting)
Click Organize

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

The Main Window

The main window has three parts.

Input and Output cards (top left) are where you drop files and choose a destination.
The Preview (center) shows exactly where every file will go before anything moves.
The Inspector (right) holds your settings for this run: Operation, Format, Destination, Structure, the Result path and a Summary.

Below them is the Activity card, a short history of your recent runs.

Squirrel follows your Mac's appearance. To force Light or Dark, go to Preferences → General → Appearance.

The Input Card

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

What you can drop in:

A single folder
Multiple folders at once
Individual files
Folders containing subfolders. Squirrel finds all files recursively

While you drag: The card highlights and tells you how many files you are about to add. Release to add them.

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).

Clearing the card: Click the × button on the Input card to remove everything you loaded and return to the empty state. Your destination stays as it was.

Removing single files: Click the × button on any file row in the Preview to exclude it from the run. The file stays where it is. It is just skipped.

Files Squirrel cannot read: If Squirrel cannot read a folder, the card says "Some files can't be read". Choose Open System Settings to grant access, or Choose Again to pick something else.

Empty folders: You can drop an empty folder. It contributes 0 files, and Organize stays disabled until at least one file is loaded.

The Output Card

The Output card is where your files will land. Drag a folder onto it, click it to browse, or press ⌘O.

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)

Clearing the card: Click the × button on the Output card to clear the destination. Squirrel returns to the default output folder from Preferences, if you set one. If you did not, the card goes back to empty.

Read-only destinations: If you drop a folder or drive that Squirrel cannot write to, it shows an error. Clear it and choose a writable location.

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

Dropping a single file on the Output card does nothing. The destination must be a folder.

The Inspector

The Inspector on the right of the main window holds the settings for the current run. Changing them updates the Preview and the Result immediately.

Operation is Copy or Move. See Running Organize.
Format is the date structure: Year / Month / Day, Year / Month, Year, or Custom.
Destination is a picker of your saved destination presets. Choose None to clear the current destination and pick a folder yourself.
Structure is a picker of your saved structure presets. Choose None to organize with whatever is set in Preferences → Folders (or Super Folders).
Result shows the folder path your files will land in, for example 2026/06/28/. With Super Mode on, it ends with the type folder and shows a SUPER label.
Summary counts your files, conflicts and suspicious dates.

When Format is locked: If a Structure Preset is selected, Format locks and shows the preset's format. Hover over it to see why. This is expected. The preset is fully controlling the structure for this run. Your own Preferences are never changed by selecting a preset. If you choose a custom structure, Format is greyed out for the same reason.

Saving presets: To save the current destination or structure as a preset, use the Save options in the Destination and Structure pickers. See Destination Presets and Structure Presets.

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.

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. You do not 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 do not 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.

What's not allowed: A bare / on its own, a leading slash, or two slashes in a row are treated as invalid. Squirrel shows an error rather than guess what you meant. If you want no date folders at all, use {ROOT}.

The {ROOT} Token

{ROOT} is for one specific case: you want no date folders at all, 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 is active, the other token chips grey out.
If Super Mode is off, files land directly in your destination.
If Super Mode is on, files land in type folders directly under your destination, with no date nesting.

Example: Destination is DesktopClean, Structure is {ROOT}, Super Mode is on. The result is DesktopClean/RAW/, DesktopClean/Photo / Image/, and so on, with no date folders.

Super Folders

Turn on Super Mode at the top of the Folders tab, and it becomes the Super Folders tab, so the tab bar always shows whether it is on.

The first time you turn it on, Squirrel asks you to confirm and explains what is about to change. Check Don't show this again to skip it in future. You can switch back to Normal Mode at any time.

Super Mode is teal. Wherever you see teal in Squirrel (the type folders in the Preview and the Stash, the SUPER label, the Super Mode switch), it means Super Mode is on. With Super Mode off, nothing is teal.

What Super Mode does

Once it is on, Squirrel sorts your files by type as well as date. A type folder is added after your date structure automatically.

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 has two columns:

Categories (left) is where you manage which file types belong to which folder.
Folder Structure (right) has the same date and format controls as the Folders tab, a Live Preview of your combined result (date structure plus type folder), and a Save Current Structure... button to save this setup as a Structure Preset.

Categories, out of the box

Squirrel starts you off with 14 built-in categories: RAW, Photo / Image, Illustration, Design, Desktop Publishing, Documents, 3D, eBooks, Video, Video Projects, Audio, Audio Projects, Archives, and Code / Development. Any file type Squirrel does not recognize goes into Uncategorized, so nothing gets lost.

Every category is yours to change.

Renaming a category: Double-click its name, type a new one, and press Return. Press Escape to cancel.

Adding a file type Squirrel already knows: Click the + on a category's header. Search for the type by name.

Adding a file type Squirrel does not know: Type it into the same search field. A leading dot is optional, so .psd and psd work the same. It is added to that category right away.

Moving or removing a file type: Click any file type chip. Choose a different category to move it, or remove it. Removing a file type asks you to confirm first.

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

Deleting a category: Click the − on a category. Squirrel confirms before deleting. Its file types fall back to Uncategorized, so nothing is lost.

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

Searching: Use the search field above the categories to find a category or a file type quickly.

Everything you customize is remembered across restarts. Custom file types stay on your Mac and are never sent anywhere.

Structure Presets

Structure Presets save a complete folder-structure setup under a name, so you can switch between workflows in one click without reconfiguring the Folders tab.

What's saved in a preset: the format, the Custom Format string (including {ROOT}, if used), the Month Format at the moment you save (changing your global Month Format later does not change existing presets), and whether Super Mode is on.

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

Saving a preset:

Build the structure you want in Preferences → Super Folders (or Folders)
Click Save Current Structure... at the bottom of the tab, or use the Structure picker in the Inspector, or Preferences → Presets
Check the live preview, give it a name, and save

Using a preset: Choose it from the Structure picker in the Inspector. It applies to the current run only. Your own Preferences are left untouched. Choose None in the picker to go back to them.

Managing presets: Go to Preferences → Presets to edit, rename or delete a Structure Preset. Editing opens the same editor you used to create it, filled in with its saved values. Deleting asks you to confirm first.

Running Organize

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

Folders in the Preview show a count of the files inside. Click a folder to expand or collapse it.

Review the Preview. If everything looks right, click Organize or press ⌘↩.

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 keep your originals. Use Move when you are done with the source and want to clean up.

While Squirrel is organizing: The Preview becomes a progress panel with the number of files done, a progress bar and the file being processed. The Inspector and the Input and Output cards are dimmed until the run is over.

Stopping a run: Click Stop, or press ⌘↩ again. Squirrel stops after the file it is working on. Files already organized stay where they landed, and Squirrel shows "Organize cancelled".

Warnings

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

Duplicate Files

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

For each duplicate, choose:

Skip: do not copy or move this file. Leave it as it 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 choice for every duplicate at once. The default is Skip.

Suspicious Dates

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

Continue: organize the file using that date as it is.
Skip: leave the file out of this run.

Disk Space

If the total size of your files is more than the free space at the destination, Squirrel warns you and disables Organize.

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

When Organize Finishes

When the run is over, the Preview becomes a result panel.

Green check: the files were organized. The panel shows the number of files, their total size, how long it took, and how many were skipped.
Amber warning: every file was skipped, usually because they already exist at the destination. Nothing was organized.

Two buttons close the panel:

Done dismisses it. You can also press Escape. Your input clears and your destination stays set, ready for the next batch.
Open The Stash opens The Stash on the run you just finished. This button appears when Use The Stash is on in Preferences.

After a run, the Reset button is called New Run.

The Stash

The Stash is a browser for the files you just organized. It looks and works like Finder, and it mirrors the folders Squirrel actually created, whether that is date folders, type folders or {ROOT}.

The Stash is a browser, not a file manager. It does not rename, move or delete anything. Use it to confirm a run went where you expected, then use Finder for anything else.

Opening The Stash:

Press ⌘⇧S, or choose View → Open The Stash
Click the Stash button in the main window's toolbar
Click Open The Stash on the result panel after a run

Right after a run, The Stash opens on the first file Squirrel organized. It is selected, its folder is open, and the preview panel shows it. The Stash always shows the most recent successful run. Organizing again replaces what it shows.

The window:

Sidebar (left): your run by year and month, with a count on each folder. Click a folder to go there.
Content (center): the files and folders, in the view mode you choose.
Path bar (bottom): the full path of the folder you are in. Click any part to jump to it.
Preview panel (right): details for the selected item (see below).

Toolbar: From left to right, Back and Home, a button to show or hide the sidebar, the view mode buttons, Show in Finder, a button to show or hide the preview panel, and the search field.

View modes:

Icons: thumbnails of your files, with a size slider. Double-click a folder to open it.
List: an expandable outline with size, kind and modified date, and a row-height slider.
Columns: Finder-style side-by-side columns that open to the full path of the file you are on.

The preview panel

Select a file to see it in the preview panel.

A large preview, the file name and its kind and size
Three buttons: Quick Look, Show in Finder and Open
Information: Kind, Size, Dimensions, Created, Modified, Last Opened and Where
Camera (photos): camera, lens, focal length, aperture, shutter and ISO, when the photo has them
Video (video files): Duration, Resolution, Codec and Frame Rate

For a folder, the panel shows its kind, number of items and location. With nothing selected, the panel is empty.

Searching

Type in the search field to look through everything in the run, not just the folder you are in. Results appear as one list with each file's folder underneath. Select a result to see it in the preview panel, or open its folder. Clear the field to return to where you were.

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 more than one item
Arrow keys move the selection, and open or close folders in List and Columns
Return opens the selected item
Space shows a Quick Look preview of the selected file
Drag a file out of The Stash to Finder to copy it there

Turning The Stash on or off: In Preferences → General, use the Use The Stash switch. When it is off, the Stash button, the View → Open The Stash item, ⌘⇧S and the Open The Stash button all go away.

The Activity Window

The Activity window is the full history of your organize runs. Open it with ⌘⌥0, or choose View → Open Activity Window.

Runs are grouped by day. Each run shows:

A status mark: a green check for success, an orange warning for partial, a red × for failed
What happened, such as "Copied 176 files"
The time, total size and how long it took

Click a run to expand it. Each file shows its name, where it went, and when. Recent entries read "just now".

Searching and filtering: Type in the search field to find a file by name. Use the filter button next to it to show only Success, Partial or Failed runs. Choose All to see everything again.

The smaller Activity card in the main window shows your latest runs. Press ⌘⇧A to show or hide it.

Destination Presets

Save your most-used output folders as presets so you do not have to drag them in every time.

Saving a preset:

Set your output destination
Choose to save it as a preset from the Destination picker in the Inspector
Give it a name (for example, "Jones Wedding", "Client SSD", or "Archive Drive")
The preset is saved and appears in the picker

Using a preset: Choose it from the Destination picker in the Inspector. The destination loads immediately. Choose None to clear it.

Managing presets: Go to Preferences → Presets to rename, add or delete destination presets. Presets you add there appear in the main window immediately, and the other way around. Deleting a preset asks you to confirm first.

Preferences

Open Preferences with ⌘, or from the Squirrel menu. The window resizes to fit each tab.

General

Default output folder: the destination Squirrel starts with. Click Choose to pick one
Operation: Copy or Move as your default
Conflict resolution: what Squirrel does with duplicates by default (Skip, Overwrite or Rename)
Appearance: System, Light or Dark
Use The Stash: turns The Stash on or off. See The Stash
Reset All Data: clears all activity history, presets, saved destinations, categories and preferences. Squirrel asks you to confirm with Reset Everything, then returns to its original state and shows the Welcome screen again

Folders / Super Folders

See The Folders Tab, Custom Format & the {ROOT} Token and Super Folders. 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.

Keyboard Shortcuts

Shortcut	Action
⌘R	Reset (New Run, after a run)
⌘↩	Organize. While organizing, Stop
⌘O	Choose the output folder
⌘,	Open Preferences
⌘⇧A	Show or hide the Activity card
⌘⌥0	Open the Activity window
⌘⇧S	Open The Stash
⌘⇧L	Export diagnostic log
Escape	Dismiss the result panel
Space	Quick Look preview (in The Stash)
Return	Open the selected item (in The Stash)
Arrow keys	Move selection and open or close folders (in The Stash)

Getting Help

If you would like a refresher on the basics, choose Help → Re-read First Run to see the Welcome screen again.

Need more help? Visit getochre.app/support.php. To include a report with your message, press ⌘⇧L to export a diagnostic log. It contains no file names or personal information, only the app version, your preferences and activity counts.