email

Email Agent Skill

✅ PRE-FLIGHT VERIFICATION

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

1. ✅ This SKILL.md file loaded successfully
2. ✅ You can see version 2.5.0 at the bottom of this file
3. ✅ You can see the preferred email addresses section (Mark, Julie, Rose, Ellerton/Michael)
4. ✅ 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, manual Gmail API calls)

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 API via Ruby script 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 → [email protected]
• Julie Whitney → [email protected]
• Rose Fletcher → [email protected]
• Jayson Bernstein → [email protected]
• Susan Butch → [email protected]
• Kevin Blair → [email protected]
• Ryan Walsh → [email protected]

Project-Specific Contacts:

• Ellerton Whitney / Michael Whitney (when in ellerton project) → [email protected]
  • ⚠️ GREETING NAME: Address as "Michael" (not Ellerton)
  • Applies to all email communications in the ellerton project context

Team Aliases:

• ALT Team (when in american_laboratory_trading project) → Send to all four:

  • [email protected]
  • [email protected]
  • [email protected]
  • [email protected]

• Dreamanager Team or Five Star Team → Send to all four:

  • [email protected]
  • [email protected]
  • [email protected]
  • [email protected] (Dreamanager context)

Context-Sensitive Routing:

• Ed Korkuch → Context-based email selection:

  • [email protected] - For Dreamanager project-related communications
  • [email protected] - 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 [email protected] 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 [email protected] 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 [email protected] 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 [email protected]

2. Security Review (🔴 CRITICAL - MANDATORY)

🔴 CRITICAL: BEFORE composing ANY email, MUST scan ALL content for sensitive information:

NEVER Include These in Emails (Zero Tolerance):

• ❌ API Tokens - Including app-specific tokens, bearer tokens, service tokens
• ❌ API Keys - AWS keys, Google API keys, service API keys, authentication keys
• ❌ Access Tokens - OAuth tokens, JWT tokens, session tokens, refresh tokens
• ❌ Passwords - Current, temporary, default, or any password variations
• ❌ Auth Credentials - Username/password pairs, login credentials, auth strings
• ❌ Private Keys - SSH keys, PGP keys, certificates, signing keys
• ❌ Database Credentials - Connection strings, database passwords, DB URLs with credentials
• ❌ Credit Card Information - Full numbers (use last 4 digits only if absolutely necessary)
• ❌ Social Security Numbers - Or any government-issued ID numbers
• ❌ Secret Environment Variables - AWS credentials, secret keys, config secrets

🔴 CRITICAL API Token Examples (MUST REDACT):

❌ WRONG: "The API token is: j22pamuqie56upqinzeeNj"
❌ WRONG: "Use api_token=abc123xyz456 for authentication"
❌ WRONG: "Bearer token: eyJhbGciOiJIUzI1NiIsInR5cCI6..."

✅ CORRECT: "I've configured the API token (redacted for security)"
✅ CORRECT: "API token: ...XXXX (last 4 chars: Nj)"
✅ CORRECT: "The authentication token has been set up in the system"
✅ CORRECT: "Token configured (see secure documentation for access)"

When Sensitive Info Must Be Referenced:

• Reference it exists but NEVER include actual value
• Use "...XXXX" notation with last 4 characters only if verification needed
• Direct recipient to secure channel (secure docs, password manager, encrypted communication)
• Provide system location where they can find it securely

Scanning Procedure (MANDATORY):

1. 🔍 Scan user's original request for any sensitive data
2. 🔍 Scan email body you're about to compose for any secrets
3. 🔍 Scan code snippets or technical examples for credentials
4. 🔍 Scan URLs for embedded tokens (e.g., ?token=... or ?api_key=...)
5. 🔍 Scan configuration examples for default/example credentials
6. 🔒 REDACT immediately if ANY sensitive data found

Remember: Email is NOT ENCRYPTED. When in doubt, redact it out. NEVER compromise security for convenience.

3. Date & Theme Selection

Determine Current Date:

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

Apply Theme:

• Check for matching national holiday (takes priority)
• Otherwise use seasonal theme based on date
• See references/seasonal_themes.md for detailed styling

Season Ranges:

• 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. Handle Attachments

Detect Attachment Requests:

• Keywords: "attach", "attachment", "include", "send with", "along with", "please see attached"
• File references: Specific paths, file names, document descriptions
• Examples: "attach the report", "include invoice.pdf", "send with the contract"

File Path Resolution:

• Absolute paths: Use directly (e.g., /Users/name/Documents/report.pdf)
• Relative paths: Resolve to absolute using current working directory
• File names only: STOP and ask user for full absolute path
• User workspace: Check common locations (~/Documents, ~/Downloads, current directory)

File Validation (🔴 CRITICAL - MANDATORY):

1. Check existence: Verify file exists at specified path using File.exist?(path)
2. Verify readability: Ensure file can be accessed and read
3. Size awareness: Gmail has 25MB total attachment size limit
   • Warn if single file >10MB
   • Calculate total size for multiple attachments
   • Suggest alternatives (cloud storage links) for large files

Multiple Attachments:

• Support array of file paths: ["file1.pdf", "file2.docx", "image.png"]
• Validate each file individually before proceeding
• All files must exist and be readable
• Total size must not exceed Gmail's 25MB limit

Attachment Array Format:

attachments: [
  "/absolute/path/to/report.pdf",
  "/absolute/path/to/invoice.xlsx",
  "/absolute/path/to/presentation.pptx"
]

Supported File Types:

• Documents: .pdf, .doc, .docx, .txt, .rtf
• Spreadsheets: .xls, .xlsx, .csv
• Prese

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