name: email description: Send and draft professional emails with seasonal HTML formatting, authentic writing style, contact lookup via Google Contacts, security-first approach, and Google Gmail API via Ruby CLI. This skill should be used for ALL email operations (mandatory per RULES.md). category: communication version: 3.0.0

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 2.5.0 at the bottom of this file
✅ You can see the preferred email addresses section (Mark, Julie, Rose, Ellerton/Michael)
✅ 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 → mark@dreamanager.com
Julie Whitney → julie@dreamanager.com
Rose Fletcher → rose@dreamanager.com
Jayson Bernstein → jayson@alt.bio
Susan Butch → sbutch@alt.bio
Kevin Blair → kblair@alt.bio
Ryan Walsh → rwalsh@alt.bio

Project-Specific Contacts:

Ellerton Whitney / Michael Whitney (when in ellerton project) → ewhitney@dailyaffairsnow.com
- ⚠️ 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:
- jayson@alt.bio
- sbutch@alt.bio
- kblair@alt.bio
- rwalsh@alt.bio
Dreamanager Team or Five Star Team → Send to all four:
- mark@dreamanager.com
- julie@dreamanager.com
- rose@dreamanager.com
- ed@dreamanager.com (Dreamanager context)

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 (🔴 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):

🔍 Scan user's original request for any sensitive data
🔍 Scan email body you're about to compose for any secrets
🔍 Scan code snippets or technical examples for credentials
🔍 Scan URLs for embedded tokens (e.g., ?token=... or ?api_key=...)
🔍 Scan configuration examples for default/example credentials
🔒 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):

Check existence: Verify file exists at specified path using File.exist?(path)
Verify readability: Ensure file can be accessed and read
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
Presentations: .ppt, .pptx, .key
Images: .jpg, .jpeg, .png, .gif
Archives: .zip, .tar, .gz
Any file type Gmail accepts (most common formats)

Security Considerations:

Verify filenames don't contain sensitive information
Ensure files don't contain credentials or API keys
Check file content if generating programmatically
Warn about potentially sensitive file types (e.g., .env, .key, .pem)

6. 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

7. Send or Draft

Primary Method: Google Gmail API via CLI

Use the gmail_manager.rb script for all email operations:

Send Email (without attachments):

echo '{
  "to": ["recipient@example.com"],
  "subject": "Subject Line",
  "body_html": "<html>...</html>",
  "cc": [],
  "bcc": [],
  "attachments": []
}' | ~/.claude/skills/email/scripts/gmail_manager.rb send

Send Email with Attachments:

echo '{
  "to": ["recipient@example.com"],
  "subject": "Monthly Report",
  "body_html": "<html><p>Please see the attached monthly report.</p></html>",
  "cc": [],
  "bcc": [],
  "attachments": [
    "/Users/arlenagreer/Documents/monthly_report.pdf",
    "/Users/arlenagreer/Documents/summary_charts.xlsx"
  ]
}' | ~/.claude/skills/email/scripts/gmail_manager.rb send

Create Draft (without attachments):

echo '{
  "to": ["recipient@example.com"],
  "subject": "Draft Subject",
  "body_html": "<html>...</html>",
  "cc": [],
  "bcc": [],
  "attachments": []
}' | ~/.claude/skills/email/scripts/gmail_manager.rb draft

Create Draft with Attachments:

echo '{
  "to": ["recipient@example.com"],
  "subject": "Draft with Files",
  "body_html": "<html><p>Draft content with attachments.</p></html>",
  "cc": [],
  "bcc": [],
  "attachments": ["/absolute/path/to/document.pdf"]
}' | ~/.claude/skills/email/scripts/gmail_manager.rb draft

Important Notes:

BCC to arlenagreer@gmail.com is automatically added by the script
No need to manually include in BCC field - script handles it
For multiple recipients, just list all addresses in the to array
JSON input via STDIN, JSON output via STDOUT

First-Time OAuth Setup:

# Script will prompt with authorization URL if not authenticated
~/.claude/skills/email/scripts/gmail_manager.rb send

# Follow the instructions:
# 1. Visit the provided authorization URL
# 2. Grant access to Gmail, Calendar, and Contacts
# 3. Copy the authorization code
# 4. Complete authorization:
~/.claude/skills/email/scripts/gmail_manager.rb auth <YOUR_CODE>

OAuth Scopes:

https://www.googleapis.com/auth/gmail.modify - Send, draft, and read emails
https://www.googleapis.com/auth/calendar - Calendar operations (shared token)
https://www.googleapis.com/auth/contacts - Contact lookups (shared token)

Shared Token: Uses the same OAuth token as calendar and contacts skills at ~/.claude/.google/token.json

Bundled Resources

Scripts

scripts/gmail_manager.rb

Send and draft emails via Google Gmail API
Automatic BCC to arlenagreer@gmail.com
Shared OAuth token with calendar and contacts skills
Requires: ~/.claude/.google/client_secret.json and ~/.claude/.google/token.json

Commands:

# Complete OAuth authorization
gmail_manager.rb auth <code>

# Send email (JSON input via STDIN)
echo '{"to":["test@example.com"],"subject":"Test","body_html":"<p>Hello</p>"}' | gmail_manager.rb send

# Create draft (JSON input via STDIN)
echo '{"to":["test@example.com"],"subject":"Draft","body_html":"<p>Draft</p>"}' | gmail_manager.rb draft

# List messages (optional query parameter)
echo '{"query":"is:unread","max_results":10}' | gmail_manager.rb list

Output Format:

Success: {"status": "success", "operation": "send", "message_id": "...", "thread_id": "...", "recipients": {...}}
Error: {"status": "error", "error_code": "...", "message": "..."}

Exit Codes:

0: Success
1: Operation failed
2: Authentication error
3: API error
4: Invalid arguments

OAuth Scopes:

https://www.googleapis.com/auth/gmail.modify
https://www.googleapis.com/auth/calendar
https://www.googleapis.com/auth/contacts

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 API Unavailable:

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

Attachment Issues:

File not found:
- STOP email workflow immediately
- Display error: "❌ Attachment file not found: [path]"
- PROMPT user: "Please provide the correct absolute path for [filename]"
- WAIT for user response - do not proceed without valid path
File not readable (permission denied):
- STOP and report: "❌ Cannot read file: [path] (Permission denied)"
- Suggest user check file permissions: ls -la [path]
- Ask for alternative file or corrected permissions
- WAIT for resolution before proceeding
File too large (>10MB individual, >25MB total):
- Warn: "⚠️ Attachment is [size]MB. Gmail limit is 25MB total."
- For large files: "Consider using cloud storage (Google Drive, Dropbox) and sharing a link instead."
- Ask user: "Would you like to proceed with attachment, use a cloud link, or remove the file?"
- WAIT for user decision
Multiple attachment validation failure:
- List all files with issues: "❌ The following attachments have problems:"
- Show specific error for each file (not found, unreadable, too large)
- WAIT for user to resolve all issues before proceeding
Sensitive file detected (.env, .key, .pem, credentials):
- STOP immediately with warning: "🚨 WARNING: Potentially sensitive file detected: [filename]"
- Explain risk: "This file type typically contains credentials or secrets."
- Ask: "Are you sure you want to attach this file? (yes/no)"
- If yes, remind about security review step
- If no, ask for alternative or proceed without attachment

Pre-Send Checklist

🔴 CRITICAL: Security (Check FIRST - MANDATORY):

✅ API Tokens: ALL tokens redacted or removed (ZERO TOLERANCE)
✅ API Keys: No AWS, Google, or service API keys visible
✅ Passwords: No passwords or credentials of any kind
✅ Access Tokens: OAuth, JWT, bearer tokens all redacted
✅ URLs: Checked for embedded tokens (?token=, ?api_key=, auth parameters)
✅ Code Examples: Configuration and code snippets sanitized
✅ Log Outputs: System logs and debug output sanitized
✅ Database Credentials: Connection strings and DB passwords removed
⚠️ IF ANY SENSITIVE DATA FOUND: STOP immediately and redact before sending

🔴 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

Attachments (if applicable):

✅ All attachment file paths are absolute and valid
✅ All files exist and are readable (verified with File.exist?)
✅ Total attachment size <25MB (Gmail limit)
✅ Individual files <10MB (warn if larger)
✅ Attachment filenames are professional and descriptive
✅ No sensitive files accidentally attached (.env, .key, .pem, credentials)
✅ Filenames don't contain sensitive information
✅ Attachment content referenced appropriately in email body

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

Attachments:

# Validate file exists
File.exist?("/path/to/file.pdf")

# Include in JSON payload
"attachments": ["/absolute/path/to/file.pdf"]

# Multiple files
"attachments": ["/path/file1.pdf", "/path/file2.xlsx"]

Version History

3.3.0 (2025-12-04) - Added project-specific contacts section with Ellerton Whitney / Michael Whitney for ellerton project (ewhitney@dailyaffairsnow.com). Includes greeting name override - must be addressed as "Michael" in all ellerton project communications.
3.2.0 (2025-11-20) - ATTACHMENT SUPPORT DOCUMENTATION: Added comprehensive attachment workflow documentation. New section 5 "Handle Attachments" with file validation, path resolution, size limits, and security checks. Updated Send/Draft examples with attachment field. Enhanced Pre-Send Checklist with 8 attachment validation items. Added 5 attachment error handling scenarios. Quick Reference updated with attachment validation examples. Technical capability existed since v3.0.0 but was undocumented - now fully documented and integrated into workflow.
3.1.0 (2025-11-12) - Added preferred email addresses for American Laboratory Trading team members (Jayson Bernstein, Susan Butch, Kevin Blair, Ryan Walsh). Added team aliases: "ALT Team" for american_laboratory_trading project (sends to all four ALT members), and "Dreamanager Team"/"Five Star Team" (sends to Mark Whitney, Julie Whitney, Rose Fletcher, Ed Korkuch at their @dreamanager.com addresses).
3.0.0 (2025-11-09) - Migrated to Google CLI pattern using gmail_manager.rb Ruby script. Now uses google-apis-gmail_v1 gem with AUTH_GMAIL_MODIFY scope for direct Gmail API access. Shares OAuth token (~/.claude/.google/token.json) with calendar and contacts skills. Automatic BCC injection handled by script. Himalaya CLI available as fallback. Future-ready for email reading capabilities. NOTE: Attachment support was included in gmail_manager.rb (lines 106-132 send_email, 171-197 draft_email) but not documented in SKILL.md until v3.2.0.
2.5.0 (2025-11-04) - Removed Halloween atmospheric theme as scheduled. Emails now return to standard seasonal themes (Fall theme for current period: September 23 - December 20).
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

email

SKILL.md