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imsg

List, review, and send iMessage or SMS conversations from macOS Messages.app.

2|Updated May 23, 2026
Search Tags:#messaging#cli#macos#attachments#sms#imessage#messagesapp
One-click install
npx skills add https://github.com/enclawed/enclawed-oss --skill imsg-enclawed
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: imsg
Source: https://github.com/enclawed/enclawed-oss/tree/main/skills/imsg
Command: npx skills add https://github.com/enclawed/enclawed-oss --skill imsg-enclawed

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

This Skill removes the friction of working with Apple Messages by letting you list chats, review conversation history, watch for new messages, and send iMessage or SMS replies from a terminal workflow.

Core Features & Use Cases

  • Chat Discovery: Find recent conversations and identify the right recipient before taking action.
  • Conversation Review: Inspect message history, including attachment-aware views when you need more context.
  • Message Sending: Deliver text messages or attachments through iMessage or SMS on macOS Messages.app.
  • Use Case: A user wants to text a family member that they will be late, confirm the exact recipient, and send the message only after reviewing the content and service choice.

Quick Start

Ask the skill to find the correct Messages.app chat, confirm the recipient and message text, and then send the iMessage or SMS once you approve it.

Frequently Asked Questions about imsg

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I send iMessage or SMS from the command line on macOS?▼

The imsg CLI lets you send iMessage or SMS from the command line by interfacing with macOS Messages.app, requiring Full Disk Access and Automation permissions to deliver outbound messages to phone numbers or Apple IDs.

Can I list and review past iMessage conversations using a CLI tool?▼

Yes, you can list and review past iMessage conversations using this CLI tool, which provides chat discovery and message history lookup with attachment-aware views directly from macOS Messages.app.

What macOS permissions are required to manage Messages.app from the terminal?▼

To manage Messages.app from the terminal, you need macOS Full Disk Access and Automation permissions, which allow the imsg CLI to perform deterministic message operations like chat discovery and outbound messaging.

Does sending SMS from the macOS CLI support attachments?▼

Sending SMS from the macOS CLI supports attachments, allowing you to deliver files to recipients while also providing attachment-aware views when reviewing message history through the imsg tool.

What is the best way to automate text messaging on macOS without opening the Messages app?▼

The best way to automate text messaging on macOS without opening the Messages app is using a CLI tool like imsg, which handles chat discovery, conversation review, and outbound iMessage or SMS delivery directly from the terminal.

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