Mac automation with Shortcuts: the triggers worth setting up, and where they stop
Most Mac automation advice is either a screenshot tour of the Shortcuts app or a wall of AppleScript. Neither answers the question you actually have: which automations survive a real working week, and which ones you build once, admire, and never trigger again. The pattern is clear enough — automations earn their keep replacing something you do on a schedule or on an event, and they disappoint when you ask them to replace something you do constantly.
Two different things both called "a shortcut"
The Shortcuts app holds shortcuts (a sequence of actions you run) and automations (a trigger that runs a shortcut for you). Different sidebar sections, different problems. A shortcut you run saves keystrokes. An automation saves you having to remember.
The second one only arrived on the Mac in macOS 26 Tahoe. Before that, Macs had the Shortcuts app but no Automation tab — triggers were an iPhone and iPad feature, and anything event-driven meant Folder Actions, Calendar alarms, or a launch agent. On macOS 15 or earlier, the first half of this article applies and the second half doesn't yet.
Eight ways to run a shortcut (most people know one)
Open a shortcut, open its details pane, and you're looking at every place macOS will surface it. Apple documents all of these:
| Where | How you set it up | Best for |
|---|---|---|
| Keyboard shortcut | Add Keyboard Shortcut, then press the keys | Anything you run twice a day or more |
| Menu bar | Pin in Menu Bar | Things you run occasionally and want to see |
| Quick Action | Use as Quick Action | Acting on files you right-click in Finder |
| Services menu | Services Menu in the details pane | Acting on selected text in any app |
| Finder | Finder under Quick Actions | The Action menu in a Finder window |
| Dock | File → Add to Dock | Shortcuts you want visible without a hotkey |
| Share sheet | Show in Share Sheet | Sending the current thing somewhere |
| Control Center | Run Shortcut in Edit Controls | One-handed, no hotkey to remember |
The keyboard shortcut is the one that changes your day, and it has a failure mode nobody warns you about: some combinations are reserved by the system and won't fire, and others get swallowed by whatever app is frontmost. A new hotkey that does nothing is a collision, not a bug — Mac shortcut conflicts covers how to find the app that took it. Control-Option plus a letter is nearly always free and comfortable; Control-Command plus a letter is next safest. Avoid anything with Command alone.
The automation triggers macOS 26 brought to the Mac
Shortcuts → Automation in the sidebar → the + button. Pick a trigger, then build the shortcut it runs. On a Mac the triggers include:
- Time of Day and Alarm
- Email and Message — from a specific person, or with text in the subject
- Folder — when an item is added, modified, or removed
- External Drive, Display, Wi-Fi, Bluetooth — connected or disconnected
- Battery Level and Charger
- App — opened or quit
- Focus — turning on or off; Stage Manager — turning on or off
Each carries a Run Immediately toggle and a Notify When Run toggle. Set them deliberately: an automation that asks permission every time becomes a notification you dismiss without reading, which is worse than no automation. Leave the notification on until you trust it, then turn it off.
The four that actually stick
- Folder → a downloads janitor. When an item lands in
~/Downloads, sort it — screenshots one way, PDFs another, installers left alone. People keep this one because the alternative is a folder with 4,000 items in it. - Time of Day → an end-of-day reset. At 18:00, quit the work-only apps and set a Focus. The value isn't the seconds saved; it's that the boundary happens whether or not you feel like enforcing it.
- Wi-Fi → context switching. The office network turns a Focus on, the home network turns it off. Pairs with Focus modes, which do the notification half properly.
- App → guard rails. When a specific app opens, turn on Do Not Disturb; when it quits, turn it off. The cheapest deep-work trigger there is, because it's tied to what you actually do rather than to a time you intended to do it.
Everything else is real but narrow. Display and External Drive sound far more useful than they turn out to be, which brings us to the interesting part.
Where Mac automation stops: your windows
The most-requested Mac automation among people with an external monitor is "when I plug in my display, put my windows back where they belong." macOS 26 delivered the first half of that sentence: the Display trigger genuinely fires on connect and disconnect.
The second half is thinner. Shortcuts does have window actions, under Scripting → Windows:
- Find Windows — the open windows, with filters on title, app name, width, height, X and Y position and window index, plus sort and limit
- Move Window — moves one, with a Bring to Front toggle
- Resize Window — nine fixed positions (Fit Screen, the four halves, the four quarters) or explicit Width × Height dimensions
That's a real API, and for a fixed layout on a known display it works: build it once, trigger it on display connect, four apps land in four corners. But look at those nine positions: halves, quarters, full screen. No thirds — not the two-thirds-and-a-third split that is the most useful arrangement on a wide display. To get one you drop into Dimensions and type pixel values, and pixel values are per-display, so the shortcut that works at your desk breaks on the laptop screen and breaks again on the monitor in the meeting room.
None of that touches the real problem anyway. Restoring a layout on plug-in is a once-a-day event. Rearranging windows is a hundred-times-a-day event — a doc beside a browser, the editor widened, the terminal pushed to the bottom third. No trigger fires for that, because the trigger is you deciding mid-thought that the window should be elsewhere. That wants a fast manual control, not a script.
That's the gap Let's Tile is built for: press one shortcut, a grid drops over the current window, steer with the arrow keys, press return. Nothing to memorise and no pixel values — the free 3 × 2 grid gives halves, thirds, two-thirds, quarters and full screen, including the thirds Shortcuts can't express, and it's the same keystrokes on every display. Pro ($9.99 once, no account, no subscription) adds grids you define yourself and a different grid per display, remembered automatically, which answers "my monitor is back" better than any automation does.
The same logic covers the other half. An automation can open an app; it can't get you to the specific window you're picturing, because only you know which one that is. That's Let's Switch and Option-Tab. Between the two, "where do windows go" and "which window do I want" stop needing a trigger at all.
A sane starting set
Build in this order: one keyboard shortcut for the thing you do most, the downloads folder automation, one Focus automation tied to an app or a network — then stop. Add more only when you catch yourself repeating something, not because a trigger exists. Four automations you trust beat twenty you half-remember.
Frequently asked questions
Do Mac automations work when the Mac is asleep? No. The Mac has to be awake for a trigger to fire. A time-of-day automation scheduled while the lid was closed runs when the Mac wakes, not at the scheduled minute.
Can I run a shortcut from Spotlight? Apple's documentation of the ways to run a shortcut lists the Dock, Control Center, Finder, the Quick Actions menu, the Touch Bar, the Services menu, a keyboard shortcut and the Share sheet — not Spotlight. For a type-a-few-letters launcher, that's a launcher app's job.
Why doesn't my new keyboard shortcut do anything? Almost always a collision — with a system shortcut you can't override, or with the frontmost app, which gets first refusal on every key combination. Try it in Finder; if it fires there and not in your editor, the editor is taking it.
Can an automation arrange my windows on a schedule? It can move and resize specific windows to halves, quarters, full screen, or explicit pixel dimensions. It can't do thirds without pixel math, and hard-coded values are tied to one display size. Workable for a fixed daily layout; wrong tool for ongoing rearrangement.