How to make Sidecar connect automatically at login

What macOS does, and does not do

Apple gives you two ways to start Sidecar: Control Center → Screen Mirroring, or System Settings → Displays, the Add Display (+) menu, then your iPad. Both are manual, every time.

System Settings → Displays → Advanced has a switch called “Automatically reconnect to any nearby Mac or iPad”. It reads like the answer and it is not: it belongs to Universal Control, which shares one keyboard and mouse with an iPad that keeps running iPadOS. It does not bring Sidecar back after a restart.

Sidecar also ends when the Mac sleeps or you log out, and it cannot run at the login window at all. Anything that automates it works inside a logged-in session.

Make the manual route one click

1. On macOS 26 or 27, open System Settings → Menu Bar and turn on Screen Mirroring.
2. On macOS 15 or earlier, open System Settings → Control Center, find Screen Mirroring and choose Always Show in Menu Bar.
3. Click the new menu bar icon and pick your iPad. That is the whole connection.

If the iPad is not in the list, the cause is almost always one of the settings in the Sidecar compatibility check.

Put it on a keyboard shortcut

A shortcut saves the trip to the menu. It does not start Sidecar at login or bring it back after a drop; you still press the key each time.

Scripts that click for you, and why they keep breaking

Most free recipes are AppleScript that opens Control Center or Displays settings and clicks the iPad the way you would. It needs Accessibility permission for whatever runs it: Terminal, Script Editor, Shortcuts, Keyboard Maestro, or sshd if you trigger it over SSH.

The weakness is that the script depends on the exact layout of Apple’s menus. Published scripts broke with macOS 13.5, again across 15.1 to 15.3, and the Control Center approach stopped working in macOS 26, which pushed people to scripting System Settings instead. They also match menu labels in English, so they fail on a Mac set to another language, and they can pick an Apple TV that sits above the iPad in the list.

If you use one, expect to fix it after each major macOS upgrade, and keep the menu bar route as your fallback.

SidecarLauncher: a command-line switch

1. Download SidecarLauncher from its GitHub releases page. It is unsigned, so macOS blocks the first run; allow it under System Settings → Privacy & Security.
2. Run ./SidecarLauncher devices to list the iPads your Mac can see.
3. Connect with ./SidecarLauncher connect "My iPad", using the name exactly as listed, and end the session with ./SidecarLauncher disconnect "My iPad".

Because it does not click through menus, it survives interface changes better than a script. It is still a hobby project: its author confirms it on macOS 14, and on macOS 26 when built from source.

Its known failure is the one that matters for automation: connect fails with error -203 when the iPad is locked or asleep, even though the iPad still appears under devices. Wake and unlock the iPad, then retry. Users have also reported a black screen when it was triggered while the Mac itself was locked, so run it only in an unlocked session.

Running it at login, and after a drop

To start Sidecar without pressing anything, the script or SidecarLauncher has to run when you log in: add it under System Settings → General → Login Items, or install a LaunchAgent in ~/Library/LaunchAgents with RunAtLoad set.

A single attempt at login usually fails. For the first seconds after login Wi‑Fi and Bluetooth are still coming up, and the iPad is often asleep on the desk. Whatever you run has to wait and retry for a minute or two instead of giving up on the first error.

Login is only half of it. Nothing tells a script that Sidecar dropped, so after the Mac wakes or a cable is pulled you are back to manual. A few open-source projects add a background agent that watches for wake and unlock and reconnects with growing pauses between attempts; they are unsigned and lightly tested, so read the code before you install one.

Get the iPad side ready

1. The same Apple Account on both devices, with two-factor authentication on.
2. Wi‑Fi, Bluetooth and Handoff on, on both, even if you use a cable, and the iPad not sharing its cellular connection.
3. On a cable, tap Trust on the iPad the first time. A cable is also the steadier connection and keeps the iPad charged; see wired vs wireless Sidecar.
4. Nothing can start Sidecar on a locked iPad; the best any tool can do is wait until you wake it. An iPad that lives on a stand and a charger is easier to automate with a longer Auto-Lock under Settings → Display & Brightness.

If the Mac has no monitor

Everything above assumes the Mac already has a screen. On a Mac mini with nothing plugged in there is no display to start from: Sidecar typically connects and drops within seconds, and tools such as BetterTouchTool report failure. The Mac needs a display to exist first, from an HDMI dummy plug or a virtual display, and it has to reach the desktop without you, which means automatic login and FileVault off.

That setup has its own guide: connecting an iPad to a Mac mini as its display.

Which option does what

SideMini starts Sidecar when you log in, waits if the iPad is asleep and connects the moment you wake it, brings it back about two seconds after a dropped connection, and reapplies extend or mirror and your resolution every time. On a Mac with no monitor it gives the Mac a screen first, so the iPad can become its only display.