server/scripts/test_email.py

import asyncio
import os
import sys
from dotenv import load_dotenv

# Add server directory to path
sys.path.append(os.path.join(os.getcwd(), "server"))

load_dotenv()

async def test_email_config():
    print("🔍 Diagnosing Email Configuration...")
    
    smtp_host = os.getenv("SMTP_HOST", "smtp.gmail.com")
    smtp_port = int(os.getenv("SMTP_PORT", "587"))
    smtp_user = os.getenv("SMTP_USER")
    smtp_password = os.getenv("SMTP_PASSWORD")
    
    print(f"📡 SMTP Host: {smtp_host}:{smtp_port}")
    print(f"👤 SMTP User: {smtp_user}")
    print(f"🔑 SMTP Password: {'****' if smtp_password and smtp_password != 'your-app-password' else 'MISSING/PLACEHOLDER'}")
    
    if not smtp_user or not smtp_password or smtp_password == "your-app-password":
        print("\n❌ CRITICAL: SMTP credentials are not configured or are still using placeholders.")
        print("💡 TIP: If using Gmail, you must generate an 'App Password' from your Google Account settings.")
        return

    try:
        import aiosmtplib
        from email.mime.text import MIMEText
        from email.mime.multipart import MIMEMultipart
        
        print("\n🚀 Attempting to send test email...")
        
        message = MIMEMultipart()
        message["From"] = smtp_user
        message["To"] = smtp_user # Send to yourself
        message["Subject"] = "🏥 Customer Agent - SMTP Test"
        
        body = "Congratulations! Your SMTP configuration is working correctly."
        message.attach(MIMEText(body, "plain"))
        
        await aiosmtplib.send(
            message,
            hostname=smtp_host,
            port=smtp_port,
            start_tls=True,
            username=smtp_user,
            password=smtp_password,
            timeout=10
        )
        print("\n✅ SUCCESS: Test email sent successfully!")
        
    except Exception as e:
        print(f"\n❌ FAILED: {str(e)}")
        if "AuthenticationFailed" in str(e):
            print("💡 TIP: Verify your username and App Password. Ensure 'Less Secure Apps' is NOT what you're using for Gmail (it's deprecated).")
        elif "TimeoutError" in str(e):
            print("💡 TIP: Check your firewall or internet connection. Port 587 might be blocked.")

if __name__ == "__main__":
    asyncio.run(test_email_config())