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Lookout keeps its data in one folder on each machine, and a few files of its own in each project folder.

Lookout's folder

~/.lookout, in the home folder of the user Lookout runs as. Only that user can read it.

PathHolds
lookout.dbyour projects and chats: every message, tool call and to-do list
settings.jsonyour settings
customize.jsonyour connectors, and which skills and plugins are on
providers/your provider sign-ins and API keys, each in a file only you can read, and the plan usage each provider last reported
secrets/your agents' secret values and the passwords of their site logins (the passwords sealed), and your connectors' signing keys. Only you can read them, and they never go into an agent's own folder or its export
connectors/your connectors' sign-ins and secrets, what their tools may do, and their recent activity
projects/a folder for each project folder: its checkpoints, chat transcripts, the full output of long tool results, the tool output compaction cleared, and the context each summary replaced; and a repo- folder for each git repository with its project memory (a folder outside git keeps its memory in its own folder)
memory/your memory in the Everywhere scope
skills/your skills in the Everywhere scope
plugins/the plugins you installed
attachments/the images and files you attached to messages, and the images and screenshots an agent viewed (where an image compaction cleared is read back from)
browser/the browser agents drive. profile/ is the profile every chat shares, and sections/ holds one for each sidebar section whose agents share their own: the cookies and site storage of every site an agent signed in to, so treat them like saved passwords. Lookout caps each profile's web cache at 32 MB. sessions/ keeps each browser session's screenshots, downloads and page text too long for the chat. Deleting a section removes its profile: see Driving a browser
agents/a folder for each agent with everything it owns: its working folder, its memory, its transcripts, its checkpoints and its photo
worktrees/the folders of chats that run in a worktree, and in <project>/.pool/ removed ones kept for the next worktree chat and, on a Mac, the checkout new ones are cloned from
workspaces/folders Lookout made for projects with no folder of yours, such as Start from scratch
models/the speech model dictation downloads the first time you dictate
dictation/each dictation until its text is in the message box (the recording), then its text for a day, readable only by you
shells/a record of each command an agent is running, with its output so far, so Lookout can pick it up again after a restart
network/this machine's place on your account: its device key, its session and the names of your other machines
cli/the lookout command's releases, where the install line installed it
desktop/the Mac app's logs

In a project folder

Lookout reads these files from your project:

FileWhat it does
AGENTS.md, CLAUDE.md, .lookout/rules/, .cursor/rules/the project's rules, read from each of its folders when a chat starts, and again at the next step after an edit: see Rules
.gitignore, .lookoutignore, .cursorignorepaths the agent's file tools leave alone, in any folder of the project: see Keep the agent out of files
.lookout/mcp.jsonthe project's connectors: see Share connectors with a project
.lookout/skills/the project's skills
.lookout/worktree.jsonthe commands run when a worktree is made or removed, the PATH and variables for the project's commands, and the commands the project requires: see The worktree file

And writes these, in .lookout/:

FileWhat it holds
.lookout/terminals/the output of each command the agent runs, one file per command. Once the folder is removed, they go to terminals/ in its data folder instead, so the folder is never made again
.lookout/.gitignorekeeps the files above out of git. rules/ and skills/ stay yours to commit. A .gitignore you wrote there yourself is left as it is

Logs

WhereWhat
~/.lookout/desktop/server.logwhat the Mac app's server prints. Help › Show Logs in Finder opens its folder
~/.lookout/desktop/update.logeach update check, download and restart of the Mac app
~/Library/Caches/com.arcadia.lookout/updates/the updates the Mac app downloaded. Help › Show Updates in Finder opens it
journalctl --user -u lookout -fthe service on a Linux server, run as the user Lookout runs as. The installer prints the command for your install
~/Library/Logs/lookout/node.logthe service on a Mac that runs the lookout command without the app

What an export holds

Export in a chat's menu saves the whole chat as a .zip named after its title. The Mac app asks where to save it.

In the archiveWhat it holds
README.mdwhat is where in the archive
export.jsonwhat the archive holds, and which files the chat named that were gone
thread.json, project.jsonthe chat's and the project's settings: title, model, effort, mode, folder
entries.jsonlevery message, tool call and result, in order
todos.jsonthe chat's to-do list
usage.jsonthe tokens each turn used, and the totals
checkpoints.json, diffs/the chat's checkpoints and the diffs between them
transcript/the chat's transcript, and those of its subagents
agent-tools/the full output of long tool results
attachments/the images attached to its messages
terminals/, spill/the command output and cleared tool output the chat named

The archive holds what the chat saw, so it can contain secrets. See What an export contains.

Delete Lookout's data

  1. To take the machine off your account first, see Sign out or leave your account.
  2. On a machine with the lookout command, uninstall it as CLI shows. Its releases are in ~/.lookout/cli, so deleting the folder alone leaves the command and its service with nothing to run.
  3. Quit Lookout.
  4. Delete ~/.lookout. This machine's chats, settings, checkpoints, memory, sign-ins and worktrees go with it: merge or push a worktree's work first.

Your project folders stay as they are. Delete a project's .lookout/ folder to remove Lookout's files from it.

  • Rules: The instruction files a chat reads from each of its folders, how an edit reaches a running chat, and the ignore files that keep the agent out of paths.
  • Safety: What the agent can reach on your machine, what limits it, and how to undo what it did.
  • Troubleshooting: Find your symptom and its fix, run the doctor check, and collect what to send when you need help.