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imessage

Send and receive iMessages and SMS on macOS with SMS fallback.

Updated Aug 27, 2026
Search Tags:#automation#validation#macos#sms#imessage#messages-app#delivery-failure
One-click install
npx skills add https://github.com/cris-m/flopsy --skill imessage-cris-m
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: imessage
Source: https://github.com/cris-m/flopsy/tree/main/src/team/templates/skills/imessage
Command: npx skills add https://github.com/cris-m/flopsy --skill imessage-cris-m

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Send and receive iMessages and SMS via Apple Messages on macOS, with delivery failure recovery and recipient format validation.

Core Features & Use Cases

  • Send iMessages and SMS to contacts by name, Apple ID, or phone number
  • Validate recipient formats and automatically fallback to SMS if iMessage is unavailable
  • Provide recovery guidance and status updates for delivery failures
  • Use case: reply to an iMessage conversation or initiate a new one from the bot

Quick Start

Ask to send an iMessage to a contact by name or number and let the tool manage delivery checks and SMS fallback automatically.

Frequently Asked Questions about imessage

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

FAQPage Schema
How do I automate sending iMessage and SMS on macOS?▼

You can automate sending iMessage and SMS on macOS by routing messages through the Apple Messages app. The automation validates recipient formats and falls back to SMS if iMessage delivery is unavailable.

What happens when an iMessage delivery fails on macOS?▼

When an iMessage delivery fails on macOS, the automation provides recovery guidance, status updates, and an automatic fallback to SMS to ensure the message reaches the recipient.

Can I send an iMessage to a contact using their name instead of a phone number?▼

Yes, you can send an iMessage to a contact by name, Apple ID, or phone number. The tool validates the recipient format before attempting message delivery.

Do I need the Messages app open to send automated iMessages on macOS?▼

Yes, you need macOS with the Messages app open and a configured iMessage gateway. These prerequisites are required for the automation to send messages and handle delivery failures.

How does SMS fallback work when iMessage is unavailable?▼

SMS fallback triggers when iMessage delivery is not possible. The automation detects the delivery failure and automatically resends the message as an SMS to ensure successful delivery.

Are there limitations to automating messages through the macOS Messages app?▼

The main limitation is platform dependency: automating messages requires macOS with the Messages app open and a configured iMessage gateway to handle the delivery and SMS fallback processes.

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