Email + Calendar Integration — Automated Scheduling & Follow-ups¶

Architecture Overview¶

┌──────────┐     ┌──────────────┐     ┌───────────┐
│  Email   │────▶│  Automation  │────▶│ Calendar  │
│  Server  │     │    Layer     │     │  Server   │
└──────────┘     └──────┬───────┘     └───────────┘
                        │
                  ┌─────▼──────┐
                  │  Hermes    │
                  │  Agent     │
                  └────────────┘

The automation layer reads incoming emails, extracts scheduling intent or follow-up triggers, and creates or updates calendar events accordingly.

MCP Server Setup¶

Email Servers¶

Gmail MCP Server — provides list_gmail_messages, search_gmail, and get_gmail_message tools. Configure with OAuth credentials from Google Cloud Console with the Gmail readonly scope. This lets the agent scan inboxes for meeting requests, scheduling emails, and follow-up triggers.

Outlook MCP Server — provides equivalent tools for Microsoft 365 mailboxes. Requires Azure AD app registration with Mail.Read scope. Supports shared mailboxes, useful for team inboxes like scheduling@example.com.

Calendar Servers¶

Google Calendar MCP Server — provides list_my_calendar_events, search_my_calendar, and event detail retrieval. Configure with Google Calendar API scope. Supports multiple calendars — separate personal and team calendars.

Outlook Calendar MCP Server — provides the same capabilities for Microsoft 365 calendars. Handles delegated calendars and room resource lookups.

Core Automation Scenarios¶

1. Meeting Scheduling from Email¶

Trigger: New email arrives containing scheduling language ("let's meet", "find time", "schedule a call", Calendly/Doodle link).

Workflow: 1. Scan inbox for scheduling-related emails (cron: every 10 minutes) 2. Extract proposed times, duration, and attendees from email body 3. Check availability on target calendar(s) using list_my_calendar_events 4. If times are proposed: validate against availability, flag conflicts 5. If no times proposed: find the next 3 open slots based on working hours 6. Draft reply with availability OR confirm the proposed time 7. Mark email with "scheduling-pending" label until confirmed

Cron expression: */10 * * * * — checks inbox for new scheduling emails every 10 minutes during business hours.

2. Follow-Up Automation¶

Trigger: Email sent to a prospect or client with no reply after N days.

Workflow: 1. Monitor sent folder for emails tagged "needs-follow-up" 2. After [N] business days without reply, create a calendar reminder for the sender 3. Draft a gentle follow-up email template personalized with the original thread context 4. If still no reply after [2N] days: escalate to a calendar task with higher priority 5. If [3N] days: move to "cold" status and log for CRM update

Configuration: Define follow-up windows per contact category (hot lead: 3 days, warm lead: 5 days, client: 7 days).

Cron expression: 0 8 * * 1-5 — runs once each weekday morning to check for follow-up needs.

3. Availability Checking¶

Trigger: Someone asks "when are you free?" or a scheduling link is shared.

Workflow: 1. Agent reads the email requesting availability 2. Calls list_my_calendar_events for the requested date range 3. Identifies open slots based on working hours (configurable: default 9 AM–5 PM, timezone-aware) 4. Respects buffer rules (no back-to-back meetings, minimum 15-minute gaps) 5. Formats availability as a clean bulleted list with timezone notation 6. Optionally generates booking link text for insertion in the reply

Working hours config:

working_hours:
  monday: "09:00-17:00"
  tuesday: "09:00-17:00"
  wednesday: "09:00-17:00"
  thursday: "09:00-17:00"
  friday: "09:00-15:00"
  timezone: "America/Chicago"
  buffer_minutes: 15
  max_meetings_per_day: 6

4. Meeting Preparation Briefs¶

Trigger: 30 minutes before a scheduled meeting.

Workflow: 1. Agent detects upcoming meeting on calendar (cron: checks every 15 minutes) 2. Searches email for the meeting thread — pulls recent correspondence with attendees 3. Extracts action items, open questions, and decisions from previous meeting notes 4. Compiles a one-page prep brief: agenda, previous context, open items, preparation notes 5. Sends the brief via email or posts to the meeting's Slack channel 6. Includes links to relevant documents and previous meeting summaries

Cron expression: */15 * * * * — checks for upcoming meetings every 15 minutes.

Cron Schedule Summary¶

Task	Cron	Description
Scan for scheduling emails	`/10 * * *`	Detect meeting requests in inbox
Follow-up check	`0 8 * * 1-5`	Weekday morning follow-up sweep
Availability responder	On-demand	Triggered by specific email detection
Meeting prep brief	`/15 * * *`	Generate prep materials before meetings
Daily calendar digest	`0 7 * * *`	Morning email with today's schedule

Implementation Notes¶

Rate Limiting¶

Both Gmail and Outlook APIs have rate limits. Implement exponential backoff in your automation scripts. For high-volume inboxes, batch email scanning into a single operation rather than per-message calls.

Security Considerations¶

Use read-only API scopes where possible — the agent should suggest, not autonomously send emails or create calendar events without human review.
Store OAuth tokens securely; rotate refresh tokens on a schedule.
Never log email bodies or calendar event details to plaintext files.

Testing¶

Start with a "dry run" mode that logs proposed actions without executing them. After a week of dry runs that produce sensible output, enable execution one automation at a time. Monitor the first month closely — edge cases in scheduling language and timezone handling are the most common failure modes.

Extending¶

Add CRM integration to log meetings against contacts. Connect Slack to post daily schedule summaries to your direct-message channel. Wire up task management (Notion, Monday, Linear) to create prep tasks for meetings automatically.