Outlook Automation Skill

Automate Classic Outlook on Windows using the `outlookctl` CLI tool. This skill enables AI-assisted email management with built-in safety guardrails.

What This Skill Does

Requirements

Key Safety Features

1. **Draft-First Workflow**: All emails are created as drafts first, never auto-sent

2. **Explicit Confirmation**: Sending requires user approval with `--confirm-send YES`

3. **Preview Before Send**: Always show email preview to user before sending

4. **Audit Logging**: All send operations are logged for accountability

Available Commands

Check Outlook Status

```bash

outlookctl doctor

```

Verifies Classic Outlook is running and COM automation is available.

List Emails

```bash

List recent emails (metadata only by default)

outlookctl list --count 10

List from specific folder

outlookctl list --folder "Sent Items" --count 5

Include body content

outlookctl list --count 3 --include-body

```

**Note**: Always retrieve metadata only unless user explicitly requests body content.

Search Emails

```bash

Search by sender

outlookctl search --from "[email protected]"

Search unread only

outlookctl search --unread-only --count 10

Search by subject

outlookctl search --subject "meeting"

Combine filters

outlookctl search --from "[email protected]" --unread-only --include-body-snippet

```

Get Specific Email

```bash

Get by Entry ID

outlookctl get --entry-id "ENTRY_ID_HERE"

Get by index in folder

outlookctl get --folder "Inbox" --index 0

```

Draft Email

```bash

Create draft with plain text

outlookctl draft --to "[email protected]" --subject "Subject" --body-text "Body content"

Create draft with HTML

outlookctl draft --to "[email protected]" --subject "Subject" --body-html "<p>HTML content</p>"

Multiple recipients

outlookctl draft --to "[email protected]" --to "[email protected]" --cc "[email protected]"

```

**Important**: Draft command creates a draft in Outlook. Always show the draft preview to the user before proceeding to send.

Send Draft Email

```bash

Send requires explicit confirmation

outlookctl send --entry-id "DRAFT_ENTRY_ID" --confirm-send YES

```

**Critical**: The `--confirm-send YES` flag is required. Never send without explicit user approval.

Save Attachments

```bash

List attachments

outlookctl attachments list --entry-id "EMAIL_ENTRY_ID"

Save all attachments

outlookctl attachments save --entry-id "EMAIL_ENTRY_ID" --output-dir "./downloads"

Save specific attachment by index

outlookctl attachments save --entry-id "EMAIL_ENTRY_ID" --output-dir "./downloads" --index 0

```

Workflow Instructions

When User Asks to Read/Search Emails

1. Use `outlookctl list` or `outlookctl search` with appropriate filters

2. Retrieve metadata only by default (no `--include-body`)

3. If user wants to read specific email content, use `outlookctl get` with the entry ID

4. Present results in a clear, organized format

When User Asks to Draft/Send Email

1. **NEVER auto-send emails**

2. Create draft using `outlookctl draft` command

3. Show the draft details to user (to, subject, body preview)

4. Ask user explicitly: "Would you like me to send this email?"

5. Only if user confirms, use `outlookctl send --entry-id DRAFT_ID --confirm-send YES`

6. Inform user that email has been sent and audit log has been created

When User Asks to Summarize Emails

1. Search/list relevant emails with `--include-body-snippet` (not full body)

2. Analyze the snippets and metadata

3. Provide concise summary

4. If deeper analysis needed, ask user if they want you to fetch full body content

Error Handling

All commands output JSON. Check for `error` field in response:

```json

{

"error": "Error description",

"error_code": "ERROR_CODE",

"remediation": "Suggested fix"

}

```

Common error codes:

If you encounter `OUTLOOK_UNAVAILABLE`, suggest user runs `outlookctl doctor` to diagnose.

Examples

Example 1: Summarize Recent Unread Emails

```bash

Get unread emails with snippets

outlookctl search --unread-only --count 10 --include-body-snippet

```

Then summarize the results for the user.

Example 2: Draft and Send Reply

1. Find email to reply to:

```bash

outlookctl search --from "[email protected]" --count 1

```

2. Create draft reply:

```bash

outlookctl draft --to "[email protected]" --subject "Re: Original Subject" --body-text "Reply content"

```

3. Show draft to user and ask for confirmation

4. If user confirms:

```bash

outlookctl send --entry-id "DRAFT_ENTRY_ID" --confirm-send YES

```

Example 3: Find and Save Attachments

1. Search for email with attachments:

```bash

outlookctl search --subject "Invoice" --count 5

```

2. List attachments:

```bash

outlookctl attachments list --entry-id "EMAIL_ENTRY_ID"

```

3. Save attachments:

```bash

outlookctl attachments save --entry-id "EMAIL_ENTRY_ID" --output-dir "./invoices"

```

Important Constraints

1. **Local Only**: This tool only works with locally installed Classic Outlook on Windows

2. **No Auto-Send**: NEVER send emails without explicit user confirmation

3. **Draft First**: Always create drafts before sending

4. **Metadata Default**: Don't fetch email bodies unless necessary

5. **Exact Confirmation**: Send confirmation must be exactly `--confirm-send YES`

Running Commands During Development

If `outlookctl` is not in PATH, use:

```bash

uv run --project "C:/path/to/outlookctl" python -m outlookctl.cli <command>

```

Or from the project directory:

```bash

uv run python -m outlookctl.cli <command>

```

Troubleshooting