Here are a few title options, focusing on the question format and incorporating key elements from the article: Option 1 (Direct and Problem-Focused): * WAMP, Sendmail, and Gmail: Why Am I Getting Co

Sendmail Integration with WAMP and PHP: Troubleshooting Connection Timeouts and Email Delivery Failures

This article discusses the challenges faced when attempting to send emails using Sendmail in conjunction with WAMP on Windows 8.1 using a Gmail account. Common errors encountered, including connection timeouts and graceful connection closures, are addressed in detail.

Connection Timeout Error (Error #10060)

When using port 465, the error "Socket Error #10060Connection timed out" is typically encountered. This occurs because Sendmail requires Administrator privileges to establish a secure connection on this port.

Graceful Connection Closure with No Email Delivery

When using port 587, the error "Connection Closed Gracefully" appears in the error log. However, no email is actually sent. This is because the appropriate SSL settings are not configured in Sendmail.ini.

Solution

1. Run Sendmail.exe as Administrator:
   Right-click Sendmail.exe, select "Properties", navigate to the "Compatibility" tab, and enable "Execute as administrator" for all users.
2. Configure Sendmail.ini for SSL:
   Add the following settings to Sendmail.ini:

smtp_ssl=ssl

3. Verify PHP Mail Settings:
   In php.ini, ensure that the following settings are configured correctly:

smtp_port = 465
sendmail_path="C:\wamp\sendmail\sendmail.exe -t"

Additional Notes:

• Ensure that the SSL module is activated in Apache.
• Verify that PHP is using the php_open_ssl and php_socket extensions.
• If using a third-party SMTP proxy like stunnel, ensure it is properly configured.

By implementing these steps, Sendmail will be granted the necessary privileges to send emails successfully using Gmail SMTP.

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