iMessageWatcher

A macOS menu bar app that monitors iMessages from a specific contact and automatically creates calendar events and reminders using a local LLM.

What It Does

iMessageWatcher watches your iMessage database for new messages from a contact you choose. When a message mentions a plan, appointment, or task, it sends the conversation to a local Ollama LLM which extracts structured data and creates calendar events or reminders automatically.

Requirements

• macOS 14+
• Ollama running locally
• Xcode Command Line Tools (xcode-select --install)

Install

Option A: Download Pre-Built App

1. Grab iMessageWatcher.zip from the latest release
2. Unzip and move iMessageWatcher.app to your Applications folder
3. Since the app is unsigned, macOS will block it on first launch — right-click the app and choose Open, then click Open again in the dialog

Option B: Build from Source

git clone https://github.com/rfaile313/iMessageWatcher.git
cd iMessageWatcher
bash build.sh
open build/iMessageWatcher.app

On first launch you'll be prompted to:

1. Grant Full Disk Access (System Settings > Privacy & Security > Full Disk Access)
2. Grant Calendar and Reminders access
3. Enter the 10-digit phone number of the contact to monitor

Ollama Setup

brew install ollama
ollama serve
ollama pull llama3:8b-instruct-q8_0   # instruct model recommended; reasoning models like deepseek-r1 tend to hallucinate

The app checks for Ollama availability on each scan cycle. The default model is llama3:8b-instruct-q8_0 but you can change it in Preferences.

Configuration

All settings are accessible from the menu bar under Preferences.

Setting	Default	Description
Contact Phone	(empty)	10-digit phone number to monitor
Poll Interval	60s	How often to check for new messages
Ollama Model	llama3:8b-instruct-q8_0	Which Ollama model to use for classification
Calendar	System default	Which calendar to create events in
Reminder List	System default	Which reminder list to use
Use Calendar	On	Create calendar events from detected plans
Use Due Reminders	Off	Send tasks to the Due app
Use Apple Reminders	Off	Create Apple Reminders from detected tasks
Use ntfy	Off	Push notifications via ntfy.sh
ntfy Topic	(empty)	Your ntfy topic name

Permissions

Permission	Why
Full Disk Access	Read the iMessage database (~/Library/Messages/chat.db)
Calendar	Create events in Apple Calendar
Reminders	Create reminders in Apple Reminders

The app will prompt you for each permission on first launch.

How It Works

The entire app is 4 files with no Xcode project and no external dependencies:

File	Purpose
main.swift	App entry point (5 lines)
AppDelegate.swift	All app logic: menu bar, SQLite scanning, LLM classification, EventKit, preferences
Info.plist	Bundle metadata and permission descriptions
build.sh	Build script: generates app icon, compiles, bundles into .app

On each poll cycle it:

1. Queries chat.db for new messages from the monitored contact
2. Builds a transcript with recent context
3. Sends it to Ollama with a structured prompt
4. Parses the JSON response into events and tasks
5. Creates calendar events / reminders as configured
6. Optionally sends a push notification via ntfy

Logs are written to ~/Library/Logs/iMessageWatcher.log.