Lookout

AI screen assistant for macOS
Sees your screen. Helps you navigate. Takes action.

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🧭 About

Every day, people call their kids, coworkers, or IT help desk to ask "how do I do this on my computer?" They're staring at the screen, trying to describe what they see, while someone on the other end guesses what they're looking at.

Lookout was inspired by helping parents and co-workers with their computers. Instead of a phone call where you're both guessing, Lookout can actually see the screen and give specific, contextual guidance — "Click the blue Save button in the top-right corner" instead of "there should be a button somewhere."

It's like a knowledgeable friend looking over your shoulder.

✨ Features

	Feature	Details
👁️	Screen Vision	Captures all connected displays via ScreenCaptureKit
🧠	Context Aware	Knows what apps are running, what windows are open
🎯	Specific Guidance	References actual buttons, menus, and text it can see
🛠️	Takes Action	Opens apps, finds files, searches your Mac
⚡	Streaming	Responses appear in real-time as they're generated
📸	Smart Capture	Auto-screenshots on first message or after inactivity; on-demand tool for follow-ups
💬	Long Conversations	Strips old images, auto-summarizes history to stay in context
🧑‍💻	Personalizable	Custom context via ~/.lookout/context.md
📝	Memory	Saves notes about you across sessions for better help over time

🚀 Install

git clone https://github.com/AnthonyDavidAdams/Lookout.git
cd Lookout
./install.sh

Builds the app, installs to /Applications, creates your config, and offers to launch.

Or build manually: ./build.sh && open Lookout.app

Prerequisites

• macOS 14 (Sonoma) or later
• Xcode Command Line Tools (xcode-select --install)
• A Claude API key

First Run

1. Click the eye icon in your menu bar
2. Enter your Claude API key
3. Grant Screen Recording when prompted
4. Ask anything about your screen

🎨 Personalize

Edit ~/.lookout/context.md to tell Lookout about yourself:

I'm not very technical, please explain things simply.
I use my Mac for photo editing with Lightroom and Photoshop.
My name is Mom.

Or edit directly in the app: right-click menu bar icon → Settings → Context tab

Lookout also learns about you over time — it saves notes about what you work on, what you struggle with, and your preferences in ~/.lookout/notes.md.

💡 Usage

Action	How
Toggle panel	Left-click menu bar eye icon
Menu	Right-click menu bar icon
Move panel	Drag anywhere
Close	Click the X or left-click the icon

Example Questions

"What apps do I have open?" "How do I change my wallpaper?" "Can you find my recent PDFs?" "Open Safari for me" "I'm trying to export this document — where's the export button?"

🔧 How It Works

Pure Swift, zero dependencies. Built with:

• SwiftUI — floating chat panel
• ScreenCaptureKit — multi-display capture (excludes own window)
• Claude API — vision + tool use with streaming responses
• NSPanel — non-activating floating window

Tools Available to the AI

Tool	What it does
capture_screen	Take a fresh screenshot of all displays
list_applications	See what's installed on the Mac
search_files	Spotlight search for files and folders
open_item	Open any app, file, or folder
save_note	Remember something about the user
read_notes	Recall notes from previous sessions

Architecture

Lookout/
├── install.sh                        # One-click installer
├── build.sh                          # Build from source
└── Lookout/
    ├── LookoutApp.swift              # Entry point
    ├── AppDelegate.swift             # Menu bar + panel
    ├── FloatingPanel.swift           # NSPanel subclass
    ├── Models/Message.swift
    ├── Views/
    │   ├── ChatView.swift            # Chat interface
    │   ├── MessageView.swift         # Markdown message bubbles
    │   └── SettingsView.swift        # API key + context editor
    └── Services/
        ├── ScreenCaptureService.swift      # Multi-display capture
        ├── ClaudeAPIService.swift          # Streaming + tool use
        ├── ConversationManager.swift       # History + summarization
        ├── SystemContextService.swift      # Running apps + windows
        ├── CustomContextService.swift      # ~/.lookout/context.md
        └── ActionService.swift             # Tool implementations

📄 License

CC BY-NC 4.0 — free for non-commercial use with attribution.

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Provided as a public utility by Earth Pilot — Mission Support for Spaceship Earth.