name	email
description	Send and draft professional emails with seasonal HTML formatting, authentic writing style, contact lookup via Google Contacts, security-first approach, and Gmail MCP integration with Himalaya CLI fallback. This skill should be used for ALL email operations (mandatory per RULES.md).
category	communication
version	2.3.0

Email Agent Skill

✅ PRE-FLIGHT VERIFICATION

CRITICAL: Before proceeding with ANY email operation, verify this skill loaded correctly:

✅ This SKILL.md file loaded successfully
✅ You can see version 2.4.0 at the bottom of this file
✅ You can see the preferred email addresses section (Mark, Julie, Rose)
✅ You can see the Core Workflow section with recipient resolution

If ANY of these are missing:

🛑 STOP immediately - do NOT proceed with email
Report to user: "❌ Email skill did not load correctly"
Show the error you encountered
Ask user for guidance on how to proceed
NEVER use alternative approaches (email search, direct Gmail MCP)

Purpose

Send and draft professional emails on behalf of Arlen Greer with:

Automatic contact lookup via Google Contacts
Seasonal HTML formatting based on current date
Authentic professional writing style
Security-first approach with credential redaction
Gmail MCP primary, Himalaya CLI fallback

🔴 CRITICAL NAME RULE: User's name is "Arlen Greer" or "Arlen A. Greer"

✅ CORRECT: Arlen, Arlen Greer, Arlen A. Greer
❌ NEVER: Arlena (this is WRONG - system username confusion)
The system username is "arlenagreer" but the actual name is "Arlen"

When to Use This Skill

🔴 CRITICAL: This skill is MANDATORY for ALL email operations per RULES.md

Use this skill when:

User requests to send or draft an email
Email-related keywords detected: "email", "send", "compose", "draft", "message", "write to"
User mentions contacting someone by email
NO EXCEPTIONS - Even "simple" emails require this skill

Why Mandatory:

Provides Arlen's authentic writing style
Ensures seasonal HTML formatting
Handles contact lookup automatically
Enforces security-first approach
Maintains professional communication standards

Core Workflow

1. Recipient Resolution

Preferred Email Addresses (Skip Lookup):

These contacts have preferred email addresses that ALWAYS take precedence over Google Contacts lookup:

Mark Whitney → mark@dreamanager.com
Julie Whitney → julie@dreamanager.com
Rose Fletcher → rose@dreamanager.com

Context-Sensitive Routing:

Ed Korkuch → Context-based email selection:
- ed@dreamanager.com - For Dreamanager project-related communications
- ekorkuch@versacomputing.com - For all other topics
How to determine context:
- Dreamanager context indicators: project work, database, Rails app, deployments, features, bugs, investor/resident functionality
- Non-Dreamanager context: general consulting, other projects, non-project discussions
When in doubt: Default to ekorkuch@versacomputing.com for professional safety

Contact Lookup (for all other recipients):

~/.claude/skills/email/scripts/lookup_contact_email.rb --name "First Last"

⚠️ CRITICAL: Require BOTH first AND last name:

❌ WRONG: --name "John" or --name "Smith"
✅ RIGHT: --name "John Smith"

Error Handling:

If lookup fails (status = "error"): STOP immediately and prompt user for email
If multiple matches (note field present): Inform user, proceed with first match
Never proceed without valid email address

User Shorthands:

"bcc me" → Add arlenagreer@gmail.com to BCC field
"send to [Name]" → Look up contact email
"send to [email]" → Use email directly

🔴 CRITICAL: BCC Default Behavior:

Multiple Recipients (2+): MANDATORY - ALWAYS include arlenagreer@gmail.com in BCC field automatically
- This is NON-NEGOTIABLE - do NOT ask user permission
- Do NOT mention in conversation - just include it
- User wants copy of ALL group emails for record-keeping
Single Recipient: BCC only if user explicitly requests "bcc me"
Verification: Before sending ANY multi-recipient email, confirm BCC field includes arlenagreer@gmail.com

2. Security Review (MANDATORY)

🔒 BEFORE composing email, scan for sensitive information:

Never Include:

❌ Passwords (current, temporary, default)
❌ API keys, access tokens, auth credentials
❌ Private keys (SSH, PGP, certificates)
❌ Database credentials, connection strings
❌ Credit card information (use last 4 digits only)
❌ Social Security Numbers, government IDs
❌ Secret environment variables

When Sensitive Info Must Be Referenced:

✅ Good: "I've configured the API key (redacted for security)"
✅ Good: "API key: sk-proj-...XXXX (last 4 chars for verification)"
❌ Bad: "Here's your password: MyP@ssw0rd123"

Remember: Email is NOT ENCRYPTED. When in doubt, redact it out.

3. Date & Theme Selection

Determine Current Date:

Check system clock from <env> context
Never assume dates from knowledge cutoff

Apply Theme:

🎃 CRITICAL: HALLOWEEN THEME MANDATORY (October 30 - November 1, 2025): Use sophisticated Halloween atmospheric theme for ALL emails during this period
After November 1, 2025: Check for matching national holiday (takes priority)
Otherwise use seasonal theme based on date
See references/seasonal_themes.md for detailed styling

🎃 HALLOWEEN THEME ENFORCEMENT:

Dates: October 30, October 31, AND November 1, 2025
Mandatory: ALL outgoing emails MUST use Halloween theme during this period
No exceptions: Even routine business emails use the Halloween theme
Remove this section: On November 2, 2025

🎃 Special Halloween Theme (October 30 - November 1, 2025):

CRITICAL: This theme MUST be used for ALL outgoing emails on October 30, October 31, AND November 1, 2025. Remove this entire Halloween theme section on November 2nd, 2025.

Use this sophisticated, mature HTML theme:

<!DOCTYPE html>
<html lang="en">
<head>
  <meta charset="UTF-8">
  <meta name="viewport" content="width=device-width, initial-scale=1.0">
  <title>{{SUBJECT}}</title>
  <style>
    @keyframes moonGlow {
      0%, 100% {
        box-shadow: 0 0 40px rgba(255, 255, 255, 0.4),
                    0 0 80px rgba(255, 255, 255, 0.2),
                    0 0 120px rgba(255, 255, 255, 0.1);
      }
      50% {
        box-shadow: 0 0 60px rgba(255, 255, 255, 0.6),
                    0 0 100px rgba(255, 255, 255, 0.3),
                    0 0 160px rgba(255, 255, 255, 0.15);
      }
    }

    @keyframes cloudDrift {
      0% { transform: translateX(0); opacity: 0.8; }
      50% { opacity: 0.4; }
      100% { transform: translateX(-200px); opacity: 0.8; }
    }

    @keyframes twinkle {
      0%, 100% { opacity: 1; transform: scale(1); }
      50% { opacity: 0.3; transform: scale(0.8); }
    }

    @keyframes drift {
      0% { transform: translateY(0) rotate(0deg); opacity: 0; }
      10% { opacity: 1; }
      90% { opacity: 1; }
      100% { transform: translateY(100vh) rotate(360deg); opacity: 0; }
    }

    @keyframes floatSlow {
      0%, 100% { transform: translateY(0); }
      50% { transform: translateY(-20px); }
    }

    body {
      margin: 0;
      padding: 0;
      font-family: -apple-system, BlinkMacSystemFont, 'Segoe UI', Roboto, Oxygen, Ubuntu, Cantarell, sans-serif;
      background: radial-gradient(ellipse at center, #1a1a2e 0%, #000000 100%);
      min-height: 100vh;
      position: relative;
      overflow-x: hidden;
    }

    .moon {
      position: fixed;
      top: 80px;
      right: 100px;
      width: 120px;
      height: 120px;
      background: radial-gradient(circle at 30% 30%, #ffffff, #f5f5f5, #e0e0e0);
      border-radius: 50%;
      z-index: 1;
      animation: moonGlow 4s ease-in-out infinite;
    }

    .moon::before {
      content: '';
      position: absolute;
      width: 25px;
      height: 25px;
      background: radial-gradient(circle, rgba(180, 180, 180, 0.4), transparent);
      border-radius: 50%;
      top: 35%;
      left: 45%;
    }

    .moon::after {
      content: '';
      position: absolute;
      width: 18px;
      height: 18px;
      background: radial-gradient(circle, rgba(200, 200, 200, 0.3), transparent);
      border-radius: 50%;
      top: 55%;
      left: 25%;
    }

    .stars {
      position: fixed;
      width: 100%;
      height: 100%;
      z-index: 0;
    }

    .star {
      position: absolute;
      width: 2px;
      height: 2px;
      background: white;
      border-radius: 50%;
      animation: twinkle 3s ease-in-out infinite;
    }

    .cloud {
      position: fixed;
      font-size: 80px;
      opacity: 0.2;
      z-index: 2;
      animation: cloudDrift 40s linear infinite;
    }

    .cloud-1 { top: 100px; right: -100px; animation-delay: 0s; }
    .cloud-2 { top: 200px; right: -100px; animation-delay: 10s; }

    .leaf {
      position: fixed;
      font-size: 30px;
      animation: drift 30s linear infinite;
      z-index: 0;
    }

    .fog {
      position: fixed;
      bottom: 0;
      left: 0;
      width: 100%;
      height: 200px;
      background: linear-gradient(to top, rgba(138, 43, 226, 0.3), transparent);
      z-index: 0;
    }

    .email-container {
      position: relative;
      z-index: 10;
      max-width: 600px;
      margin: 60px auto;
      padding: 20px;
    }

    .main-content {
      background: linear-gradient(135deg,
        rgba(25, 20, 35, 0.92),
        rgba(45, 25, 55, 0.92),
        rgba(35, 25, 45, 0.92));
      backdrop-filter: blur(10px);
      border-radius: 12px;
      padding: 50px 40px;
      box-shadow: 0 8px 32px rgba(0, 0, 0, 0.4);
      border: 1px solid rgba(255, 255, 255, 0.1);
      animation: fadeIn 1s ease-out;
    }

    h1 {
      color: #b794f6;
      font-family: 'Garamond', serif;
      font-size: 28px;
      margin: 0 0 30px 0;
      text-align: center;
      font-weight: 300;
      letter-spacing: 2px;
    }

    p {
      color: #e0e0e0;
      line-height: 1.8;
      margin: 0 0 20px 0;
      font-size: 16px;
    }

    .signature {
      margin-top: 40px;
      padding-top: 20px;
      border-top: 1px solid rgba(255, 255, 255, 0.2);
      color: #d0d0d0;
      font-size: 14px;
    }

    @media only screen and (max-width: 600px) {
      .email-container { padding: 15px; }
      .main-content { padding: 30px 25px; }
      .moon { width: 80px; height: 80px; top: 40px; right: 40px; }
    }
  </style>
</head>
<body>
  <div class="moon"></div>

  <div class="stars">
    <div class="star" style="top: 15%; left: 20%; animation-delay: 0s;"></div>
    <div class="star" style="top: 25%; left: 80%; animation-delay: 0.5s;"></div>
    <div class="star" style="top: 40%; left: 10%; animation-delay: 1s;"></div>
    <div class="star" style="top: 60%; left: 70%; animation-delay: 1.5s;"></div>
    <div class="star" style="top: 70%; left: 30%; animation-delay: 2s;"></div>
    <div class="star" style="top: 35%; left: 50%; animation-delay: 0.7s;"></div>
    <div class="star" style="top: 80%; left: 60%; animation-delay: 2.5s;"></div>
    <div class="star" style="top: 20%; left: 45%; animation-delay: 1.2s;"></div>
    <div class="star" style="top: 50%; left: 85%; animation-delay: 1.8s;"></div>
    <div class="star" style="top: 65%; left: 15%; animation-delay: 2.2s;"></div>
    <div class="star" style="top: 10%; left: 65%; animation-delay: 0.3s;"></div>
    <div class="star" style="top: 75%; left: 40%; animation-delay: 2.7s;"></div>
  </div>

  <div class="cloud cloud-1">☁️</div>
  <div class="cloud cloud-2">☁️</div>

  <div class="leaf" style="left: 10%; animation-delay: 0s;">🍂</div>
  <div class="leaf" style="left: 30%; animation-delay: 5s;">🍁</div>
  <div class="leaf" style="left: 50%; animation-delay: 10s;">🍂</div>
  <div class="leaf" style="left: 70%; animation-delay: 15s;">🍁</div>
  <div class="leaf" style="left: 90%; animation-delay: 20s;">🍂</div>

  <div class="fog"></div>

  <div class="email-container">
    <div class="main-content">
      <p>Hi {{RECIPIENT_NAME}},</p>

      {{CONTENT}}

      <div class="signature">
        <p>-Arlen</p>
      </div>
    </div>
  </div>
</body>
</html>

Theme Features:

Sophisticated dark atmospheric design with purple/violet accents
Detailed moon with realistic glow and crater effects
Drifting clouds, twinkling stars, floating autumn leaves
Elegant typography with proper spacing
Mobile-responsive with adaptive sizing
No explicit "Halloween" or holiday references (mature thematic approach)

Season Ranges (for non-special dates):

Spring: March 20 - June 20
Summer: June 21 - September 22
Fall: September 23 - December 20
Winter: December 21 - March 19

4. Compose Content

Apply Arlen's Writing Style:

Professional but approachable tone
Direct and solution-oriented
Lead with status/accomplishment
Use bullets for multiple items
Offer proactive support

See references/writing_style_guide.md for:

Greeting patterns
Email structure templates
Communication scenarios
Language patterns
Closing conventions

Signature & Footer Requirements:

Standard: -Arlen
Formal: -Arlen A. Greer (for senior executives, legal, contracts)
❌ ABSOLUTELY NO AI ATTRIBUTION OR AUTOMATION NOTES
❌ NO FOOTERS beyond signature - emails must end with signature only
❌ FORBIDDEN PHRASES: "generated by", "automation", "Claude Code", "AI-generated", "Co-Authored-By"
Emails MUST appear to come directly from Arlen with no indication of automation

5. Create HTML Email

Use Template: assets/email_template.html

Replace Placeholders:

{{SUBJECT}} - Email subject line
{{RECIPIENT_NAME}} - Recipient's first name
{{CONTENT}} - Email body content

Apply Seasonal Styling:

Replace seasonal-header background
Update h1 color
Set link colors
See references/seasonal_themes.md for color palettes

Mobile Responsive:

Template includes responsive styles
Max-width: 600px
Adjusts for mobile viewports

6. Send or Draft

Primary Method: Gmail MCP

Available tools:

mcp__gmail__send_email - Send immediately
mcp__gmail__draft_email - Create draft for review

Example:

mcp__gmail__send_email({
  to: ["recipient1@example.com", "recipient2@example.com"],
  subject: "Project Update",
  htmlBody: "<html>...</html>",
  mimeType: "text/html",
  bcc: ["arlenagreer@gmail.com"] // MANDATORY for 2+ recipients - ALWAYS include automatically
})

Fallback Method: Himalaya CLI

If Gmail MCP unavailable, use Himalaya CLI.

See references/himalaya_cli.md for:

Configuration details
Send commands (plain text and HTML)
Troubleshooting

Basic HTML send:

himalaya message send << 'EOF'
From: arlenagreer@gmail.com
To: recipient@example.com
Subject: Subject Here
MIME-Version: 1.0
Content-Type: text/html; charset=utf-8

<!DOCTYPE html>
<html>...</html>
EOF

Bundled Resources

Scripts

scripts/lookup_contact_email.rb

Query Google Contacts by name
Returns email address via JSON output
Requires: ~/.claude/.google/client_secret.json and ~/.claude/.google/token.json

Usage:

~/.claude/skills/email/scripts/lookup_contact_email.rb --name "John Smith"

Output:

Success: {"status": "success", "email": "john@example.com", "name": "John Smith"}
Error: {"status": "error", "code": "NO_MATCH_FOUND", "message": "..."}

Exit Codes:

0: Success
1: No match found
2: Authentication error
3: API error
4: Invalid arguments

References

references/seasonal_themes.md

Detailed seasonal color palettes and CSS
National holiday themes with styling
Season determination logic
HTML examples for each theme

references/writing_style_guide.md

Comprehensive Arlen writing style examples
Email structure templates
Communication scenarios
Language patterns and conventions

references/himalaya_cli.md

Himalaya CLI configuration and usage
Send commands for plain text and HTML
Troubleshooting and error handling

Assets

assets/email_template.html

Base HTML email template
Mobile-responsive structure
Placeholder system for content
Ready for seasonal theme injection

Error Handling

Contact Lookup Fails:

STOP email workflow immediately
Display error: "❌ Contact lookup failed: No contact found for '[Name]'"
PROMPT user: "Please provide an email address for [Name] to continue."
WAIT for user response - do not assume or guess
Only proceed once valid email provided

Authentication Issues:

Check credentials: ~/.claude/.google/client_secret.json
Verify token: ~/.claude/.google/token.json
Re-authenticate if needed or request manual email

Gmail MCP Unavailable:

Automatically offer Himalaya CLI fallback
Provide clear instructions for CLI method
Confirm user wants to proceed

Pre-Send Checklist

🔒 Security (Check FIRST):

✅ No passwords or credentials visible
✅ API keys and tokens redacted
✅ URLs checked for embedded auth
✅ Log outputs sanitized

🔴 Name Validation (CRITICAL):

✅ No references to "Arlena" (incorrect name - must be "Arlen")
✅ All name references use "Arlen" or "Arlen Greer" or "Arlen A. Greer"
✅ Scan entire email body and footer for incorrect name variants

🚫 Footer & Attribution Validation (CRITICAL):

✅ NO automation notes ("generated by", "automation", "Claude Code")
✅ NO AI attribution ("AI-generated", "Co-Authored-By: Claude")
✅ Footer contains ONLY signature (-Arlen or -Arlen A. Greer)
✅ Email ends immediately after signature - no additional text

Content & Style:

✅ Recipient email resolved
✅ BCC VERIFICATION (CRITICAL): If 2+ recipients, arlenagreer@gmail.com MUST be in BCC field - NO EXCEPTIONS
✅ Current date verified from system clock
✅ Appropriate seasonal/holiday theme applied (Halloween theme Oct 30 - Nov 1, 2025)
✅ Writing style matches Arlen's voice
✅ Proper greeting and closing
✅ Mobile responsive HTML

Quick Reference

Contact Lookup:

~/.claude/skills/email/scripts/lookup_contact_email.rb --name "First Last"

Season Determination: Check date in <env> → Apply corresponding theme from references/seasonal_themes.md

Writing Style: Follow patterns in references/writing_style_guide.md

HTML Template: Use assets/email_template.html with seasonal styling

Signature: -Arlen (standard) or -Arlen A. Greer (formal) - NO AI attribution

Version History

2.4.0 (2025-10-30) - Added special Halloween atmospheric theme for October 30-31, 2025. Sophisticated dark design with moon, stars, clouds, and autumn leaves. Theme automatically applies to all outgoing emails on these dates. Instructions included to remove theme on November 1st, 2025.
2.3.0 (2025-10-30) - Added automatic BCC default behavior: arlenagreer@gmail.com is now automatically included in BCC field when sending to 2+ recipients (no user request needed). Single-recipient emails still require explicit "bcc me" request.
2.2.0 (2025-10-29) - Enhanced recipient resolution with preferred email addresses: Mark Whitney, Julie Whitney, and Rose Fletcher now use @dreamanager.com addresses. Added context-sensitive routing for Ed Korkuch (ed@dreamanager.com for Dreamanager project, ekorkuch@versacomputing.com for other topics).
2.1.0 (2025-10-28) - CRITICAL FIX: Added explicit name validation (Arlen vs Arlena) and strengthened footer/attribution prohibition with comprehensive pre-send checklist
2.0.0 (2025-10-23) - Restructured with skill-creator best practices: extracted references/ (seasonal_themes.md, writing_style_guide.md, himalaya_cli.md), moved script to scripts/, created assets/ with email_template.html, streamlined SKILL.md for progressive disclosure
1.7.0 (2025-10-20) - Added three new known recipient shortcuts: Mark Whitney, Julie Whitney, Rose Fletcher
1.6.0 (2025-10-19) - Added known recipient shortcut: Ed Korkuch
1.5.0 (2025-10-19) - Enhanced documentation with robustness improvements
1.4.0 (2025-10-19) - Added "bcc me" shorthand
1.3.0 (2025-10-19) - Removed AI attribution from emails
1.2.0 (2025-10-19) - Enhanced contact lookup error handling
1.1.0 (2025-10-19) - Added comprehensive security requirements
1.0.0 (2025-10-19) - Initial email skill creation

Install Skill

SKILL.md