Mac app | Lookout Docs

The Mac app runs chats on this Mac, and starts and follows chats on your other machines. It runs on Macs with Apple silicon, and updates itself.

Install

Open Download on Lookout's site, sign in when it asks, and click Download.
Open the disk image and drag Lookout into Applications.
Before the first launch, run this once in Terminal:
```
xattr -cr /Applications/Lookout.app
```
Open Lookout from Applications.

If macOS says Lookout is damaged and can't be opened, that is expected until the app is notarized: run the command in step 3 and open Lookout again.

The window shows Sign in to Lookout until this Mac is signed in and on your account.

Click Continue with browser and sign in on the page that opens. The app picks up the sign-in by itself.
If your account already has another device, the app shows Add this Mac with a code. Enter that code on the other device to add this Mac. With no other device at hand, use your Recovery Key.

The first Mac on a new account then shows Save your Recovery Key, as Account and devices describes.

Menus

Menu	Items
Lookout	About Lookout, the update item (see Update), Settings (`⌘,`)
File	New Chat (`⌘N`), Open Folder (`⇧⌘O`)
View	Toggle Sidebar (`⌘\`), Back (`⌘[`), Forward (`⌘]`), zoom and full screen
Help	Lookout Docs, Keyboard Shortcuts, What's New, Send Feedback, Show Logs in Finder, Show Updates in Finder

Keyboard Shortcuts opens Settings › Keyboard. Keyboard shortcuts lists them all. Send Feedback starts a mail to Lookout's feedback address in your mail app, with the app's version in the subject. Collect a report says what to attach when you report a problem.

Update

Lookout checks for a new version shortly after it opens, then every hour. A new version shows as Update at the bottom of the sidebar, or in the top bar while the sidebar is hidden.

Click Update. It downloads while you keep working and shows its progress, such as Updating 42%.
Click Restart to update when it shows.

Running chats pause for a moment and pick up where they left off after the restart. If you don't restart, the update installs when you quit Lookout.

To check by hand, choose Lookout › Check for Updates, or open Settings › General and click Check for updates under Software update. Two switches there change the defaults:

Setting	Default	What it does
Check for updates automatically	On	Checks shortly after Lookout opens, then every hour
Download updates in the background	Off	Downloads a new version as soon as it is found, ready to restart

Lookout installs only updates signed with its release key, and deletes a download that fails the check. A version Lookout has pulled is never installed, even when it is already downloaded. If a new version fails to start, Lookout goes back to the version you had and doesn't install that one again.

After an update, a message says which version you are on. Its What's new shows the release notes. Help › What's New, and What's new in Settings › General, open the changelog in your browser. It is for signed-in readers: sign in with your Arcadia account and it opens.

Quit with chats running

Closing the window doesn't quit: Lookout and its chats keep running, and clicking Lookout in the Dock opens the window again.

Quitting while chats run shows a warning that names them, such as A chat is still running. It also names any command the agent started that is still running: quitting stops it.

Quit Anyway pauses the running chats. Each picks up where it stopped when Lookout opens again.
Cancel keeps Lookout open.

Restarting for an update never shows this warning: the chats pause and resume on their own, and the commands they started keep running across the restart. Neither does quitting while an update is ready: Lookout installs it as it quits, stopping running commands as any quit does, and the chats resume when it opens again.

Keep this Mac awake

While Use this Mac from your other devices is on, Lookout can keep the Mac from sleeping, so chats keep running and your other devices can reach it. Set it in Settings › Devices under This Mac, with Keep awake:

Choice	What it does
When plugged in (default)	Keeps the Mac awake on power while a chat runs here or your other devices can reach it. On battery, it sleeps when idle as usual
Always	The same, on battery too
Never	macOS sleeps the Mac when idle as usual, and your other devices show it as asleep

Locking the screen or a sleeping display does not stop Lookout. Closing the lid puts the Mac to sleep unless it is on power with an external display connected.

Dictate a message

Click Dictate (the microphone) in the message box. The first time, macOS asks to let Lookout use the microphone.
Speak. A take can run up to 20 minutes, and is transcribed while you speak, so the text comes about a second after you stop whatever its length. Level bars and the take's time stand where the model's name was, and the stop button where the microphone was; while the last words are transcribed, the bars wait in a slow shimmer.
Press Enter or click the stop button to put the text at the cursor. Press Esc to throw the take away.

The text goes to the chat you recorded in. If you moved to another chat while it was transcribed, it goes onto the end of that chat's draft, and a toast opens the chat.

Lookout keeps every take on this Mac until its text is in the message box: the recording is deleted once the text is in, and the rest after a day. When Lookout doesn't answer, a toast says Dictation kept, and Retry sends the same recording again; a reload of the window picks the take up by itself. Right-click the microphone for Recent dictations, the day's last five, to insert or copy one again, or to retry or discard one that wasn't transcribed.

Dictation is transcribed on this Mac, in English. The first recording starts a one-time download of the speech model (464 MB). Until the model is ready, macOS 26 and later transcribe with the speech engine built into macOS; on an earlier macOS, a take made during the download fails and says how far the download has come.

Sounds

Lookout plays a sound when a chat finishes, but not when you stop it yourself. Turn it off in Settings › General under Sounds with Play a sound when a chat finishes. For another sound, click Choose file next to Sound and pick a sound file. Preview plays it.

Notifications

While Lookout's window is not in front, it posts a macOS notification when something needs you. Click one to open what it names.

Notification	When
The chat's title, with Finished, Needs your answer (its reply asked you something), Needs you to go on (it can't go on without you), Stopped with an error, Stopped: plan limit reached, Stopped: round limit reached, Stopped: output limit reached or Stopped early, see the summary	A project chat's turn ends while that chat isn't on screen. A turn you stopped, or one a restart paused, posts nothing
The chat's title and needs your input	A chat asks you a question
An agent's name and the first line of its message	One of your agents sends you a message
An agent's name and the first line of its reply	An agent's turn that needs you ends: its reply to you, or an answer you were waiting for that it passed on. One conversation posts at most one in five minutes
The agent and who it couldn't answer, with what went wrong	An agent's turn stops where someone must act, such as a provider that needs a new sign-in
A device's name and wants to join your Lookout account	A device asks to join your account. This one plays a sound, and the Dock icon bounces

The Dock icon's badge counts the chats you haven't read and the chats that wait on you, each once, while the window is in the background. To change how notifications show, or turn them off, open Lookout in Notifications in macOS System Settings.

Logs

Help › Show Logs in Finder opens ~/.lookout/desktop, the folder with the app's log files, such as server.log and update.log, and renderer.jsonl: the window's crashes, hangs and errors, any error the app itself didn't expect (recorded there instead of shown in a dialog), and its memory and slow frames each minute. Attach these files when you report a problem with the app.

Uninstall

To take this Mac off your account first, open Settings › Devices and click Remove this Mac from your account at the bottom of the page.
Quit Lookout.
Drag Lookout from Applications to the Trash.
If you installed the lookout command on this Mac, uninstall it as CLI shows.
To delete your chats, settings and checkpoints on this Mac too, delete the ~/.lookout folder.

Troubleshooting

Troubleshooting lists symptoms and their fixes.

Quickstart: From an invitation to a reviewed change, and back again, in eight steps.
Keyboard shortcuts: Every keyboard shortcut in the Mac app, grouped by where it works.
Troubleshooting: Find your symptom and its fix, run the doctor check, and collect what to send when you need help.