Django Gmail SMTP Authentication Issue

Based on your description, you're facing a common but frustrating issue with Gmail SMTP authentication in Django. Let me address your specific questions:

Potential Causes and Solutions

Android/Pydroid 3 Specific Issues

Yes, there can be Android-specific SMTP quirks when using Pydroid 3. Mobile environments often have different network configurations and security policies that can affect SMTP connections. The fact that your standalone scripts work but Django doesn't suggests an environment-specific issue.

Alternative Email Providers

Switching to a dedicated email service provider like Mailgun or SendGrid is often a good solution for production applications. These services:

• Provide more reliable delivery
• Offer better debugging tools
• Have simpler authentication processes
• Include analytics and monitoring

Google Security Policies

Even with an app-specific password, Google might still be blocking the connection due to:

• IP-based restrictions (especially on mobile networks)
• Unusual login patterns
• Security policies specific to your Google account

Troubleshooting Steps

1. Verify your app password is correctly entered (no spaces or typos)

2. Try explicit SSL configuration:

   PYTHONCopied
   EMAIL_BACKEND = 'django.core.mail.backends.smtp.EmailBackend'
   EMAIL_HOST = 'smtp.gmail.com'
   EMAIL_PORT = 465
   EMAIL_USE_SSL = True
   EMAIL_USE_TLS = False
   EMAIL_HOST_USER = 'myapp@gmail.com'
   EMAIL_HOST_PASSWORD = 'app-specific-password'

3. Test with a timeout setting:

   PYTHONCopied
   EMAIL_TIMEOUT = 60  # seconds

4. Check if your Google account has any security alerts that might be blocking the connection

5. Try a direct SMTP test within your Django environment:

   PYTHONCopied
   import smtplib
   from email.mime.text import MIMEText
   
   def test_smtp():
       server = smtplib.SMTP('smtp.gmail.com', 587)
       server.set_debuglevel(1)  # Enable verbose debug output
       server.starttls()
       server.login('myapp@gmail.com', 'app-specific-password')
       msg = MIMEText('Test message')
       msg['Subject'] = 'Test Subject'
       msg['From'] = 'myapp@gmail.com'
       msg['To'] = 'recipient@example.com'
       server.send_message(msg)
       server.quit()

If these steps don't resolve the issue, switching to Mailgun or SendGrid would be a practical solution, especially for production applications.