Outlook Automation

Outlook Automation

This skill enables email and calendar automation through Classic Outlook on Windows using the outlookctl CLI tool.

How to Run Commands

Run all commands using this pattern from any directory:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli <command> [options]

For convenience, define this alias at the start of your session:

alias outlookctl='uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli'

Quick Start

Before using any commands, verify the environment:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli doctor

Available Commands

Email Commands

Calendar Commands

Tip: Use --calendar "Name" to access non-default calendars (e.g., --calendar "Family").

Safety Rules

CRITICAL: Follow these rules when handling email and calendar operations:

Email Safety

1. Never auto-send emails - Always create drafts first and get explicit user confirmation before sending
2. Draft-first workflow - Use draft to create drafts, show the user a preview, then send only after approval
3. Explicit confirmation required - The send command requires --confirm-send YES flag
4. Metadata by default - Body content is only retrieved when explicitly requested

Calendar Safety

1. Meetings are drafts by default - When creating a meeting with attendees, invitations are NOT sent automatically
2. Explicit send required - Use calendar send --confirm-send YES to send meeting invitations
3. Show preview first - Always show the user meeting details before sending invitations
4. Responding is safe - Accepting/declining meetings does not require extra confirmation

Workflows

Reading and Searching Email

To list recent emails:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli list --count 10

To search for specific emails:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli search --from "sender@example.com" --since 2025-01-01

To get full message content (only when user asks):

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli get --id "<entry_id>" --store "<store_id>" --include-body

Creating and Sending Email (Draft-First)

Step 1: Create a draft

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli draft --to "recipient@example.com" --subject "Subject" --body-text "Message body"

Step 2: Show user the preview (subject, recipients, body summary)

Step 3: Only after user confirms, send the draft

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli send --draft-id "<entry_id>" --draft-store "<store_id>" --confirm-send YES

Replying to Messages

# Create reply draft
uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli draft --to "recipient@example.com" --subject "Re: Original" --body-text "Reply text" --reply-to-id "<entry_id>" --reply-to-store "<store_id>"

Saving Attachments

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli attachments save --id "<entry_id>" --store "<store_id>" --dest "./attachments"

Calendar Workflows

Viewing Calendar Events

To list upcoming events (next 7 days by default):

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar list

To list events for a specific date range:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar list --start "2025-01-20" --days 14

To view a shared calendar:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar list --calendar "colleague@example.com"

To get full event details:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar get --id "<entry_id>" --store "<store_id>" --include-body

Creating Events (Personal Appointments)

For events without attendees (no invitations needed):

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar create --subject "Focus Time" --start "2025-01-20 14:00" --duration 120

Creating Meetings (Draft-First Workflow)

Step 1: Create the meeting (saved as draft, no invitations sent)

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar create \
  --subject "Team Sync" \
  --start "2025-01-20 10:00" \
  --duration 60 \
  --location "Conference Room A" \
  --attendees "alice@example.com,bob@example.com" \
  --body "Agenda:\n1. Project updates\n2. Next steps"

Step 2: Show user the meeting preview (subject, time, attendees, location)

Step 3: Only after user confirms, send the invitations

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar send --id "<entry_id>" --store "<store_id>" --confirm-send YES

Creating Meetings with Teams Link

To include a Teams meeting URL in the body:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar create \
  --subject "Virtual Meeting" \
  --start "2025-01-20 15:00" \
  --duration 30 \
  --attendees "team@example.com" \
  --teams-url "https://teams.microsoft.com/l/meetup-join/..."

Note: The Teams URL is embedded in the meeting body. For full Teams integration (automatic link generation), create the meeting in Outlook manually.

Creating Recurring Events

Weekly standup every Monday and Wednesday:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar create \
  --subject "Daily Standup" \
  --start "2025-01-20 09:00" \
  --duration 15 \
  --recurrence "weekly:monday,wednesday:until:2025-12-31"

Responding to Meeting Invitations

To accept a meeting:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar respond --id "<entry_id>" --store "<store_id>" --response accept

To decline a meeting:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar respond --id "<entry_id>" --store "<store_id>" --response decline

To tentatively accept:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar respond --id "<entry_id>" --store "<store_id>" --response tentative

To respond without notifying the organizer:

uv run --project "C:/Users/GordonMickel/work/outlookctl" python -m outlookctl.cli calendar respond --id "<entry_id>" --store "<store_id>" --response accept --no-response

Output Format

All commands output JSON with a consistent structure. Key fields:

• version: Schema version (currently "1.0")
• success: Boolean for operation result
• Message IDs include entry_id and store_id for stable references

Reference Documentation

For detailed information, see:

• CLI Reference - Complete command options
• JSON Schema - Output format details
• Security - Data handling and safety
• Troubleshooting - Common issues

Requirements

• Windows with Classic Outlook running
• uv installed and in PATH
• outlookctl project at: C:/Users/GordonMickel/work/outlookctl

Error Handling

If commands fail, check:

1. Classic Outlook is running (not New Outlook)
2. doctor command passes all checks
3. Message IDs are valid and not expired