SMTP Settings

SMTP Email Setup for Tradeboard

Gmail Configuration Options

Choose the configuration that matches your Gmail setup:

Personal Gmail (Recommended)

After migration, go to Profile → SMTP Configuration and use:

SMTP Server: smtp.gmail.com
SMTP Port: 587
Username: your-email@gmail.com
Password: [App Password - see below]
Use TLS/SSL: Yes (checked)
From Email: your-email@gmail.com
HELO Hostname: smtp.gmail.com

Google Workspace (Business Gmail)

For business domains (e.g., user@yourcompany.com):

Option 1: SMTP Relay (Recommended for Businesses)

Requirements:

• Google Workspace Admin access
• Server IP registration in Google Admin Console

Configuration:

SMTP Server: smtp-relay.gmail.com
SMTP Port: 465
Username: your-email@yourcompany.com
Password: [App Password - see below]
Use TLS/SSL: Yes (checked)
From Email: your-email@yourcompany.com
HELO Hostname: smtp.gmail.com

Setup Steps:

1. Admin Console Setup:

   • Go to Google Admin Console

   • Navigate to Apps → Google Workspace → Gmail → SMTP relay service

   • Click Add another to create new relay

   • Configure these settings:

     Allowed senders: Only addresses in my domains
     Authentication: Require SMTP Authentication
     Encryption: Require TLS encryption

   • Add your server IP address to allowed IP ranges

   • Save the configuration

2. Find Your Server IP:

   # From your Tradeboard server, run:
   curl -4 ifconfig.me
   # Or visit: https://whatismyipaddress.com/

3. Register IP in Admin Console:

   • In SMTP relay settings, add your server IP to IP addresses
   • Format: YOUR.SERVER.IP.ADDRESS/32 (e.g., 203.0.113.15/32)

Option 2: Personal Gmail Settings (Alternative)

If SMTP relay setup is complex, use personal Gmail settings:

SMTP Server: smtp.gmail.com
SMTP Port: 587
Username: your-email@yourcompany.com
Password: [App Password]
Use TLS/SSL: Yes (checked)
From Email: your-email@yourcompany.com
HELO Hostname: smtp.gmail.com

App Password Setup (Required for Both)

For Personal Gmail:

1. Go to Google Account Settings
2. Enable 2-Factor Authentication (if not enabled)
3. Select App passwords
4. Choose Mail from dropdown
5. Generate password and copy the 16-character code
6. Use this password in Tradeboard (NOT your regular password)

For Google Workspace:

1. Go to Google Account Settings
2. Admin may need to enable App Passwords:
   • Admin Console → Security → API controls → App passwords
   • Enable "Allow users to manage their app passwords"
3. Follow same steps as personal Gmail above
4. If App Passwords unavailable, ask your IT administrator

Advanced Google Workspace Configuration

Admin Console SMTP Relay Settings

For enterprise deployments, configure these advanced settings:

1. Security Settings:

   Require TLS encryption: Yes
   Require SMTP Authentication: Yes
   Only accept mail from specified IP addresses: Yes

2. Rate Limiting:

   Per-user rate limit: 10,000 messages/day
   Per-domain rate limit: 1,000,000 messages/day

3. Routing Settings:

   Also deliver to Gmail mailbox: Optional
   Store and forward: Recommended for reliability

Multiple Domain Support

If you have multiple domains in Workspace:

1. Primary Domain Configuration:

   SMTP Server: smtp-relay.gmail.com
   From Email: noreply@primarydomain.com

2. Additional Domains:

   • Add all domains to Admin Console → Domains
   • Enable SMTP relay for each domain
   • Use same SMTP settings with appropriate From Email

Troubleshooting Google Workspace

Common Error: "Mail relay denied"

Solution 1 - IP Registration:

# Check your current IP
curl -4 ifconfig.me

# Add this IP to Google Admin Console:
# Apps → Gmail → SMTP relay service → IP addresses

Solution 2 - Authentication:

• Verify App Password is correctly generated
• Ensure 2FA is enabled on the account
• Check username format (full email address)

Solution 3 - Fallback to Personal Settings:

SMTP Server: smtp.gmail.com (instead of smtp-relay.gmail.com)
SMTP Port: 587 (instead of 465)

Error: "Authentication failed"

1. Check App Password:

   • Must be 16 characters without spaces
   • Generated specifically for "Mail"
   • Account must have 2FA enabled

2. Admin Policy Check:

   Admin Console → Security → Less secure app access
   Should be: "Allow users to manage their access to less secure apps"

3. Account Verification:

   • Ensure account is not suspended
   • Check for recent password changes

Testing Your Configuration

Step-by-Step Testing

1. Save SMTP Settings in Profile → SMTP Configuration
2. Click "Debug" to test connection and view detailed diagnostics
3. Click "Send Test" to send test email to yourself
4. Check your inbox (and spam folder)
5. Try Password Reset to test end-to-end functionality

Expected Test Results

Debug Output (Success):

OK: SMTP connection successful
OK: Authentication passed
OK: TLS encryption enabled
OK: Server ready to accept messages

Debug Output (Common Issues):

FAIL: Mail relay denied → Check IP registration in Admin Console
FAIL: Authentication failed → Verify App Password
FAIL: Connection timeout → Check firewall/network settings

Testing Different Scenarios

1. Test from Different IPs: If using multiple servers
2. Test Different From Addresses: Verify domain permissions
3. Test High Volume: Check rate limiting behavior
4. Test Failed Authentication: Verify error handling

Production Deployment Best Practices

Security Recommendations

1. Use Dedicated Service Account:

   Create: noreply@yourcompany.com
   Purpose: SMTP authentication only
   Permissions: Minimal (just send email)

2. IP Whitelist Management:

   • Use static IP addresses for production servers
   • Document all registered IPs
   • Regular audit of IP permissions

3. Monitor Email Logs:

   • Track successful/failed send attempts
   • Monitor for suspicious activity
   • Set up alerts for authentication failures

Performance Optimization

1. Connection Pooling: Use persistent SMTP connections when possible
2. Rate Limiting: Respect Google's sending limits
3. Retry Logic: Implement exponential backoff for failures
4. Queue Management: Handle high-volume email sending

Common Issues & Solutions

Personal Gmail Issues

• Authentication Failed: Use App Password, not regular password
• Connection Failed: Try port 587 instead of 465
• 2FA Required: Enable 2-Factor Authentication first

Google Workspace Issues

• Mail relay denied:
  • Register server IP in Admin Console
  • Verify SMTP relay service is enabled
  • Check authentication credentials
• Admin restrictions:
  • App passwords may be disabled by admin
  • Less secure app access may be blocked
  • Contact IT administrator for policy changes
• Domain verification:
  • Ensure domain is verified in Workspace
  • Check MX records are properly configured
  • Verify user account is active

Network & Firewall Issues

• Port blocking: Ensure ports 587/465 are open outbound
• Proxy servers: Configure SMTP through corporate proxy if needed
• DNS resolution: Verify smtp.gmail.com resolves correctly

Alternative Email Providers

Microsoft 365 / Outlook

Business (Exchange Online):

SMTP Server: smtp.office365.com
SMTP Port: 587
Username: your-email@yourcompany.com
Password: [Account Password or App Password]
Use TLS/SSL: Yes (checked)
From Email: your-email@yourcompany.com
HELO Hostname: smtp.office365.com

Personal Outlook/Hotmail:

SMTP Server: smtp-mail.outlook.com
SMTP Port: 587
Username: your-email@outlook.com
Password: [Account Password]
Use TLS/SSL: Yes (checked)
From Email: your-email@outlook.com
HELO Hostname: smtp-mail.outlook.com

Yahoo Mail

SMTP Server: smtp.mail.yahoo.com
SMTP Port: 587
Username: your-email@yahoo.com
Password: [App Password from Yahoo Account Security]
Use TLS/SSL: Yes (checked)
From Email: your-email@yahoo.com
HELO Hostname: smtp.mail.yahoo.com

Custom SMTP Providers

SendGrid:

SMTP Server: smtp.sendgrid.net
SMTP Port: 587
Username: apikey
Password: [SendGrid API Key]

Mailgun:

SMTP Server: smtp.mailgun.org
SMTP Port: 587
Username: [Mailgun SMTP Username]
Password: [Mailgun SMTP Password]

Enterprise Integration

Load Balancing

For high-availability setups:

1. Configure multiple SMTP servers
2. Implement failover logic
3. Monitor server health
4. Balance email load across servers

Compliance & Logging

1. Audit Requirements:
   • Log all email send attempts
   • Track recipient information (hashed)
   • Monitor for compliance violations
2. Data Retention:
   • Configure log retention periods
   • Implement secure log storage
   • Regular compliance audits

Monitoring & Alerting

Set up monitoring for:

• SMTP connection failures
• Authentication errors
• Rate limit violations
• Unusual sending patterns

Support & Resources

Google Support Links

• Google Workspace SMTP Relay - General SMTP relay documentation
• App Passwords Setup - How to generate App Passwords
• Admin Console Guide - SMTP relay service configuration

Tradeboard Resources

• Built-in Debug: Use SMTP Debug function in profile
• Log Files: Check Tradeboard logs for detailed error messages
• GitHub Issues: Report SMTP-specific problems
• Documentation: /docs/PASSWORD_RESET.md for complete system overview

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That's it! Your Tradeboard can now send emails for password resets and notifications using your preferred email provider. Choose the configuration that best fits your organization's setup and security requirements.