Email Check Sub-Skill

Purpose

This sub-skill handles intelligent inbox triage by connecting to Gmail or Outlook via MCP, analyzing unread emails, scoring them by importance, categorizing them, and generating reply suggestions for high-priority items.

Workflow

1. Detect Available Email Provider

Check which MCP tools are available:

• Gmail: search_gmail_messages, get_gmail_messages_content_batch, get_gmail_thread_content, list_gmail_labels
• Outlook: list-mail-messages, list-mail-folder-messages, get-mail-message

Prefer Gmail if both are available (better batch operations).

2. Fetch Unread Emails

For Gmail:

search_gmail_messages(query="is:unread", max_results=50)

For Outlook:

list-mail-messages (defaults to recent messages, filter for unread)

3. Batch Fetch Email Content

For Gmail:

get_gmail_messages_content_batch(message_ids=[...])  # Up to 25 at a time

If more than 25 unread, prioritize most recent first.

For Outlook:

get-mail-message for each message (sequential)

Limit to 25 emails maximum to avoid overwhelming analysis.

4. Score Each Email (0-100)

Apply the following scoring algorithm:

Base Score: 50

Sender Recognition (+20 to -20)

• +20: VIP/known contact (domain matches user's company, appears in sent folder frequently)
• +10: Recognized sender (has prior thread history)
• 0: Unknown sender with legitimate domain
• -15: Newsletter/automated sender (bulk email headers, unsubscribe links)
• -20: Notification sender (no-reply@, noreply@, automated@)

Direct Address (+15 to -10)

• +15: Primary recipient (To: field)
• 0: CC'd (CC: field)
• -10: BCC'd or mass email (many recipients)

Thread Depth (+10)

• +10: Reply in active thread (Re: subject, multiple messages in thread)
• 0: New email (no thread history)

Urgency Keywords (+15)

Check subject and first 200 characters for:

• urgent, ASAP, deadline, action required, immediate, time-sensitive, expiring, expires, due
• +15 if any urgency keyword found

Calendar/Meeting (+20)

• +20: Calendar invite, meeting request, event notification
• Detect via attachments (ics file) or subject patterns (Invitation:, Meeting:)

Deadline Detection (+25)

Parse email body for dates/deadlines:

• +25: Deadline within 48 hours
• +10: Deadline within 7 days
• 0: No deadline or deadline > 7 days

Business Relevance (+15 to -10)

If email-profile.md exists in parent directory:

• +15: Mentions user's key topics, clients, projects
• +5: Industry-relevant keywords
• -10: Off-topic or personal (if business inbox)

Final Score Calculation

Sum all adjustments to base score of 50. Clamp to 0-100 range.

5. Categorize Emails

Based on final score:

Score Range	Category	Action
85-100	Urgent	Immediate attention, generate reply suggestions
65-84	Important	Review soon, may need action
40-64	Routine	Normal priority, review when available
20-39	Low Priority	Skim or defer
0-19	Archive	Likely noise or automated

6. Generate Reply Suggestions

For emails scored 85+ (Urgent category):

1. Read full thread context using get_gmail_thread_content or equivalent
2. Check for email-profile.md in parent directory for user's:
   • Brand voice (professional, casual, direct, warm)
   • Common sign-off
   • Industry/role context
3. Draft two reply options:
   • Brief: 1-2 sentences, direct answer
   • Detailed: 1 paragraph with context

Do NOT draft replies if:

• Email requires research beyond available context
• Email needs user decision (approve/decline, choose option)
• Email is FYI/informational only
• Email is calendar invite (suggest accept/decline/tentative instead)

In these cases, output: "This email requires your personal attention: [reason]"

7. Output Format

## Inbox Summary

**X unread emails** | Y Urgent | Z Important | W Routine | V Low Priority

### Urgent (Action Required)

| # | From | Subject | Score | Suggested Action |
|---|------|---------|-------|------------------|
| 1 | sender@domain.com | Subject line | 95 | [Reply/Review/Respond] |
| 2 | ... | ... | 88 | ... |

---

### Important

| # | From | Subject | Score | Category |
|---|------|---------|-------|----------|
| 3 | ... | ... | 78 | Meeting follow-up |
| 4 | ... | ... | 70 | Client inquiry |

---

### Routine & Low Priority

- **Routine (40-64)**: X emails - [grouped summary by sender/topic]
- **Low Priority (20-39)**: Y emails - newsletters, notifications
- **Archive (<20)**: Z emails - automated/noise

---

### Suggested Replies

#### 1. Re: [Subject] (to: sender@domain.com)

**Context:** [Why this email scored high, key points]

**Brief Option:**
> [1-2 sentence reply]
>
> [Sign-off]

**Detailed Option:**
> [Paragraph with more context/explanation]
>
> [Sign-off]

#### 2. Re: [Next urgent email]

[Repeat format]

---

### Emails Requiring Personal Attention

- **#X - [Subject]**: Needs decision on [topic]
- **#Y - [Subject]**: Requires research before responding

Scoring Signal Reference

Signal	Score Impact	Detection
Direct To: address	+15	Check To: field
VIP/known sender	+20	Domain match, sent folder history
Active thread	+10	Thread ID, Re: in subject
Urgency keywords	+15	Subject/body scan
Calendar invite	+20	.ics attachment, invite headers
Deadline <48h	+25	Date parsing in body
Deadline <7d	+10	Date parsing in body
Business relevance	+15	Match email-profile.md topics
CC'd (not primary)	-10	CC: field
Newsletter	-20	Unsubscribe link, bulk headers
Notification	-15	no-reply@ sender
Unknown sender	-10	No thread history

Reply Suggestion Guidelines

Tone Adaptation

If email-profile.md exists, adapt replies to match:

• Professional: Formal, structured, clear
• Casual: Friendly, conversational
• Direct: Brief, action-oriented
• Warm: Personable, relationship-focused

Default to professional-friendly if no profile exists.

Reply Structure

Brief Option:

• Answer the core question/request
• 1-2 sentences maximum
• Clear next step if needed

Detailed Option:

• Address all points raised
• Provide context or explanation
• 1 paragraph (3-5 sentences)
• Suggest next steps or timeline

When NOT to Draft

• Email asks for approval/decision → Suggest: "Review and approve/decline X"
• Email requires data you don't have → "This email requires your personal attention: needs [data/info]"
• Email is complex multi-part → "This email requires your personal attention: multiple decisions needed"
• Email is FYI only → Suggested Action: "Review (no response needed)"

Error Handling

No MCP Connection

If neither Gmail nor Outlook MCP is available:

Error: No email provider connected. Please ensure Gmail MCP or Outlook MCP is configured.

Empty Inbox

## Inbox Summary
**0 unread emails** - Your inbox is clear!

MCP Rate Limits

If batch fetch fails, fall back to individual message retrieval (slower but reliable).

Thread Context Unavailable

If get_gmail_thread_content fails, draft replies based on single message only (note: "Limited context - single message view").

Integration Points

email-profile.md (optional)

If exists in parent directory (../email-profile.md), use for:

• Brand voice detection
• Business relevance scoring
• Reply tone/style matching
• Common topics/clients list

Gmail-Specific Features

• Use labels to refine categorization (e.g., skip "Promotions" labeled emails)
• Check sent folder for sender recognition

Outlook-Specific Features

• Use folder structure for context (Inbox vs Focused)
• Leverage categories if available

Performance Optimization

• Batch fetch 25 emails at a time (Gmail)
• Limit analysis to 50 most recent unread
• Cache sender recognition data during session
• Prioritize most recent emails if >50 unread

Output Constraints

• Keep total output under 2000 lines
• Group routine/low priority emails by topic/sender
• Only show full details for Urgent and Important categories
• Collapse archived emails into summary count

Quality Gates

Before outputting digest:

1. Verify all urgency scores are justified with signal breakdown
2. Ensure reply suggestions are actionable (not generic)
3. Check that "personal attention" notes explain why
4. Confirm categories align with score ranges
5. Validate that batch operations completed successfully

Success Criteria

A successful email check session should:

• Identify all truly urgent emails (no false negatives)
• Minimize false positives in Urgent category (precision > 80%)
• Provide actionable reply drafts for top 3-5 emails
• Complete analysis in <30 seconds for 25 emails
• Output clear next actions for each category