A proactive AI skill that silently schedules and sends context-aware follow-ups and reminders based on conversation, calendar, and email triggers.
Install & Download
1. ClawHub CLI
The fastest way to install a skill directly from the registry.
npx clawhub@latest install proactive-messaging
2. Manual Installation
Copy the skill folder to one of these locations
~/.openclaw/skills/ <project>/skills/ Priority: Workspace > Local > Bundled
3. Prompt Installation
Copy this prompt to OpenClaw to install it automatically.
Help me install proactive-messaging using Clawhub. If Clawhub is not installed, install it first (npm i -g clawhub).
Prefer to download?
Get the raw skill files in a ZIP archive.
What is Proactive Messages?
The Proactive Messages skill enables an AI agent to act as a thoughtful digital companion by identifying significant events in a user's life and scheduling timely follow-ups. Unlike traditional reminder systems, this skill operates silently in the background of Openclaw Skills, analyzing chat history, calendar events, and incoming emails to determine when a nudge would be most valuable.
It focuses on human-like timing and tone, ensuring that messages feel natural—like a text from a friend—rather than a robotic notification. By leveraging one-shot cron jobs, the skill ensures that every interaction is purposeful and contextually relevant, whether it is checking in after a big job interview or reminding a user of a looming visa deadline.
Proactive Messages Use Cases
- Automatically checking in after a user completes a major life transition or project milestone.
- Sending a supportive message following a high-pressure presentation or meeting found on the calendar.
- Notifying the user about 'action required' emails that may have been missed during a busy day.
- Providing a gentle heads-up for recurring but forgettable appointments like dentist visits or renewals.
- Following up on emotional or stressful situations mentioned during previous conversations.
How Proactive Messages Works
- The skill monitors active conversations for triggers related to life events, transitions, or emotional states.
- A daily scan job runs at 8:00 AM local time to review the user's calendar for upcoming deadlines and unread emails for time-sensitive tasks.
- The system applies timing heuristics to determine the most appropriate moment to send a message (e.g., evening after a first day at work).
- A one-shot cron job is created with the
deleteAfterRunflag set to true, ensuring the schedule is cleaned up after execution. - The agent delivers a short, casual message at the scheduled time without ever having signaled to the user that a reminder was set.
Proactive Messages Setup
To deploy this skill within your environment, ensure you have the necessary integrations for calendar and email access. Use the following command to initialize the daily scan routine:
# Initialize the daily scan for proactive triggers
openclaw cron add --name "Proactive Daily Scan" --schedule "0 8 * * *" --payload '{"task": "scan_sources"}'
Ensure your agent's configuration allows for the creation of isolated sessions to prevent the silent scheduling from interrupting active user flows.
Proactive Messages Data Schema & Taxonomy
The skill utilizes a specific JSON structure for scheduling proactive turns via the cron system:
| Attribute | Type | Description |
|---|---|---|
name |
string | Brief context of the nudge (e.g., Proactive: Flight Check) |
deleteAfterRun |
boolean | Set to true to ensure the job is ephemeral |
schedule |
timestamp | Targeted delivery time in the user's local timezone |
sessionTarget |
string | Set to 'isolated' to manage the turn independently |
payload.message |
string | The 1-3 sentence natural language message to be delivered |
Proactive Messages Advanced Features
- Smart frequency capping to ensure the user receives no more than 5-6 proactive messages per week.
- Multi-source trigger synthesis that correlates calendar events with recent email confirmations.
- Silent scheduling logic that prevents the agent from announcing its intent to follow up, preserving the element of surprise.
- Tone-matching heuristics that adjust the message vibe between celebratory, gentle, or practical based on the trigger type.
SKILL.md
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