dcrouter/test/suite/smtpclient_email-composition/test.cep-10.receipts-dsn.ts

import { tap, expect } from '@git.zone/tstest/tapbundle';
import { startTestSmtpServer } from '../../helpers/server.loader.js';
import { createSmtpClient } from '../../helpers/smtp.client.js';
import { Email } from '../../../ts/mail/core/classes.email.js';

let testServer: any;

tap.test('setup test SMTP server', async () => {
  testServer = await startTestSmtpServer({
    features: ['DSN'] // Enable DSN support
  });
  expect(testServer).toBeTruthy();
  expect(testServer.port).toBeGreaterThan(0);
});

tap.test('CEP-10: Read receipt headers', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Create email requesting read receipt
  const email = new Email({
    from: 'sender@example.com',
    to: ['recipient@example.com'],
    subject: 'Important: Please confirm receipt',
    text: 'Please confirm you have read this message',
    headers: {
      'Disposition-Notification-To': 'sender@example.com',
      'Return-Receipt-To': 'sender@example.com',
      'X-Confirm-Reading-To': 'sender@example.com',
      'X-MS-Receipt-Request': 'sender@example.com'
    }
  });

  // Monitor receipt headers
  const receiptHeaders: string[] = [];
  const originalSendCommand = smtpClient.sendCommand.bind(smtpClient);
  
  smtpClient.sendCommand = async (command: string) => {
    if (command.includes(':') && 
        (command.toLowerCase().includes('receipt') || 
         command.toLowerCase().includes('notification') ||
         command.toLowerCase().includes('confirm'))) {
      receiptHeaders.push(command.trim());
    }
    return originalSendCommand(command);
  };

  const result = await smtpClient.sendMail(email);
  expect(result).toBeTruthy();
  
  console.log('Read receipt headers sent:');
  receiptHeaders.forEach(header => {
    console.log(`  ${header}`);
  });

  await smtpClient.close();
});

tap.test('CEP-10: DSN (Delivery Status Notification) requests', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Check if server supports DSN
  const ehloResponse = await smtpClient.sendCommand('EHLO testclient.example.com');
  const supportsDSN = ehloResponse.includes('DSN');
  console.log(`Server DSN support: ${supportsDSN}`);

  // Create email with DSN options
  const email = new Email({
    from: 'sender@example.com',
    to: ['recipient@example.com'],
    subject: 'DSN Test Email',
    text: 'Testing delivery status notifications',
    dsn: {
      notify: ['SUCCESS', 'FAILURE', 'DELAY'],
      returnType: 'HEADERS',
      envid: `msg-${Date.now()}`
    }
  });

  // Monitor DSN parameters in SMTP commands
  let mailFromDSN = '';
  let rcptToDSN = '';
  const originalSendCommand = smtpClient.sendCommand.bind(smtpClient);
  
  smtpClient.sendCommand = async (command: string) => {
    if (command.startsWith('MAIL FROM')) {
      mailFromDSN = command;
    } else if (command.startsWith('RCPT TO')) {
      rcptToDSN = command;
    }
    return originalSendCommand(command);
  };

  await smtpClient.sendMail(email);
  
  console.log('\nDSN parameters in SMTP commands:');
  console.log('MAIL FROM command:', mailFromDSN);
  console.log('RCPT TO command:', rcptToDSN);
  
  // Check for DSN parameters
  if (mailFromDSN.includes('ENVID=')) {
    console.log('  ✓ ENVID parameter included');
  }
  if (rcptToDSN.includes('NOTIFY=')) {
    console.log('  ✓ NOTIFY parameter included');
  }
  if (mailFromDSN.includes('RET=')) {
    console.log('  ✓ RET parameter included');
  }

  await smtpClient.close();
});

tap.test('CEP-10: DSN notify options', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Test different DSN notify combinations
  const notifyOptions = [
    { notify: ['SUCCESS'], description: 'Notify on successful delivery only' },
    { notify: ['FAILURE'], description: 'Notify on failure only' },
    { notify: ['DELAY'], description: 'Notify on delays only' },
    { notify: ['SUCCESS', 'FAILURE'], description: 'Notify on success and failure' },
    { notify: ['NEVER'], description: 'Never send notifications' },
    { notify: [], description: 'Default notification behavior' }
  ];

  for (const option of notifyOptions) {
    console.log(`\nTesting DSN: ${option.description}`);
    
    const email = new Email({
      from: 'sender@example.com',
      to: ['recipient@example.com'],
      subject: `DSN Test: ${option.description}`,
      text: 'Testing DSN notify options',
      dsn: {
        notify: option.notify as any,
        returnType: 'HEADERS'
      }
    });

    // Monitor RCPT TO command
    let rcptCommand = '';
    const originalSendCommand = smtpClient.sendCommand.bind(smtpClient);
    
    smtpClient.sendCommand = async (command: string) => {
      if (command.startsWith('RCPT TO')) {
        rcptCommand = command;
      }
      return originalSendCommand(command);
    };

    await smtpClient.sendMail(email);
    
    // Extract NOTIFY parameter
    const notifyMatch = rcptCommand.match(/NOTIFY=([A-Z,]+)/);
    if (notifyMatch) {
      console.log(`  NOTIFY parameter: ${notifyMatch[1]}`);
    } else {
      console.log('  No NOTIFY parameter (default behavior)');
    }
  }

  await smtpClient.close();
});

tap.test('CEP-10: DSN return types', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Test different return types
  const returnTypes = [
    { type: 'FULL', description: 'Return full message on failure' },
    { type: 'HEADERS', description: 'Return headers only' }
  ];

  for (const returnType of returnTypes) {
    console.log(`\nTesting DSN return type: ${returnType.description}`);
    
    const email = new Email({
      from: 'sender@example.com',
      to: ['recipient@example.com'],
      subject: `DSN Return Type: ${returnType.type}`,
      text: 'Testing DSN return types',
      dsn: {
        notify: ['FAILURE'],
        returnType: returnType.type as 'FULL' | 'HEADERS'
      }
    });

    // Monitor MAIL FROM command
    let mailFromCommand = '';
    const originalSendCommand = smtpClient.sendCommand.bind(smtpClient);
    
    smtpClient.sendCommand = async (command: string) => {
      if (command.startsWith('MAIL FROM')) {
        mailFromCommand = command;
      }
      return originalSendCommand(command);
    };

    await smtpClient.sendMail(email);
    
    // Extract RET parameter
    const retMatch = mailFromCommand.match(/RET=([A-Z]+)/);
    if (retMatch) {
      console.log(`  RET parameter: ${retMatch[1]}`);
    }
  }

  await smtpClient.close();
});

tap.test('CEP-10: MDN (Message Disposition Notification)', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Create MDN request email
  const email = new Email({
    from: 'sender@example.com',
    to: ['recipient@example.com'],
    subject: 'Please confirm reading',
    text: 'This message requests a read receipt',
    headers: {
      'Disposition-Notification-To': 'sender@example.com',
      'Disposition-Notification-Options': 'signed-receipt-protocol=optional,pkcs7-signature',
      'Original-Message-ID': `<${Date.now()}@example.com>`
    }
  });

  const result = await smtpClient.sendMail(email);
  expect(result).toBeTruthy();

  // Simulate MDN response
  const mdnResponse = new Email({
    from: 'recipient@example.com',
    to: ['sender@example.com'],
    subject: 'Read: Please confirm reading',
    headers: {
      'Content-Type': 'multipart/report; report-type=disposition-notification',
      'In-Reply-To': `<${Date.now()}@example.com>`,
      'References': `<${Date.now()}@example.com>`,
      'Auto-Submitted': 'auto-replied'
    },
    text: 'The message was displayed to the recipient',
    attachments: [{
      filename: 'disposition-notification.txt',
      content: Buffer.from(`Reporting-UA: mail.example.com; MailClient/1.0
Original-Recipient: rfc822;recipient@example.com
Final-Recipient: rfc822;recipient@example.com
Original-Message-ID: <${Date.now()}@example.com>
Disposition: automatic-action/MDN-sent-automatically; displayed`),
      contentType: 'message/disposition-notification'
    }]
  });

  console.log('\nSimulating MDN response...');
  await smtpClient.sendMail(mdnResponse);
  console.log('MDN response sent successfully');

  await smtpClient.close();
});

tap.test('CEP-10: Multiple recipients with different DSN', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Email with multiple recipients, each with different DSN settings
  const email = new Email({
    from: 'sender@example.com',
    to: [
      'important@example.com',
      'normal@example.com',
      'optional@example.com'
    ],
    subject: 'Multi-recipient DSN Test',
    text: 'Testing per-recipient DSN options',
    dsn: {
      recipients: {
        'important@example.com': { notify: ['SUCCESS', 'FAILURE', 'DELAY'] },
        'normal@example.com': { notify: ['FAILURE'] },
        'optional@example.com': { notify: ['NEVER'] }
      },
      returnType: 'HEADERS'
    }
  });

  // Monitor RCPT TO commands
  const rcptCommands: string[] = [];
  const originalSendCommand = smtpClient.sendCommand.bind(smtpClient);
  
  smtpClient.sendCommand = async (command: string) => {
    if (command.startsWith('RCPT TO')) {
      rcptCommands.push(command);
    }
    return originalSendCommand(command);
  };

  await smtpClient.sendMail(email);
  
  console.log('\nPer-recipient DSN settings:');
  rcptCommands.forEach(cmd => {
    const emailMatch = cmd.match(/<([^>]+)>/);
    const notifyMatch = cmd.match(/NOTIFY=([A-Z,]+)/);
    if (emailMatch) {
      console.log(`  ${emailMatch[1]}: ${notifyMatch ? notifyMatch[1] : 'default'}`);
    }
  });

  await smtpClient.close();
});

tap.test('CEP-10: DSN with ORCPT', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Test ORCPT (Original Recipient) parameter
  const email = new Email({
    from: 'sender@example.com',
    to: ['forwarded@example.com'],
    subject: 'DSN with ORCPT Test',
    text: 'Testing original recipient tracking',
    dsn: {
      notify: ['SUCCESS', 'FAILURE'],
      returnType: 'HEADERS',
      orcpt: 'rfc822;original@example.com'
    }
  });

  // Monitor RCPT TO command for ORCPT
  let hasOrcpt = false;
  const originalSendCommand = smtpClient.sendCommand.bind(smtpClient);
  
  smtpClient.sendCommand = async (command: string) => {
    if (command.includes('ORCPT=')) {
      hasOrcpt = true;
      console.log('ORCPT parameter found:', command);
    }
    return originalSendCommand(command);
  };

  await smtpClient.sendMail(email);
  
  if (!hasOrcpt) {
    console.log('ORCPT parameter not included (may not be implemented)');
  }

  await smtpClient.close();
});

tap.test('CEP-10: Receipt request formats', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Test various receipt request formats
  const receiptFormats = [
    {
      name: 'Simple email',
      value: 'receipts@example.com'
    },
    {
      name: 'With display name',
      value: '"Receipt Handler" <receipts@example.com>'
    },
    {
      name: 'Multiple addresses',
      value: 'receipts@example.com, backup@example.com'
    },
    {
      name: 'With comment',
      value: 'receipts@example.com (Automated System)'
    }
  ];

  for (const format of receiptFormats) {
    console.log(`\nTesting receipt format: ${format.name}`);
    
    const email = new Email({
      from: 'sender@example.com',
      to: ['recipient@example.com'],
      subject: `Receipt Format: ${format.name}`,
      text: 'Testing receipt address formats',
      headers: {
        'Disposition-Notification-To': format.value
      }
    });

    // Monitor the header
    let receiptHeader = '';
    const originalSendCommand = smtpClient.sendCommand.bind(smtpClient);
    
    smtpClient.sendCommand = async (command: string) => {
      if (command.toLowerCase().includes('disposition-notification-to:')) {
        receiptHeader = command.trim();
      }
      return originalSendCommand(command);
    };

    await smtpClient.sendMail(email);
    console.log(`  Sent as: ${receiptHeader}`);
  }

  await smtpClient.close();
});

tap.test('CEP-10: Non-delivery reports', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Simulate bounce/NDR structure
  const ndrEmail = new Email({
    from: 'MAILER-DAEMON@example.com',
    to: ['original-sender@example.com'],
    subject: 'Undelivered Mail Returned to Sender',
    headers: {
      'Auto-Submitted': 'auto-replied',
      'Content-Type': 'multipart/report; report-type=delivery-status',
      'X-Failed-Recipients': 'nonexistent@example.com'
    },
    text: 'This is the mail delivery agent at example.com.\n\n' +
          'I was unable to deliver your message to the following addresses:\n\n' +
          '<nonexistent@example.com>: User unknown',
    attachments: [
      {
        filename: 'delivery-status.txt',
        content: Buffer.from(`Reporting-MTA: dns; mail.example.com
X-Queue-ID: 123456789
Arrival-Date: ${new Date().toUTCString()}

Final-Recipient: rfc822;nonexistent@example.com
Original-Recipient: rfc822;nonexistent@example.com
Action: failed
Status: 5.1.1
Diagnostic-Code: smtp; 550 5.1.1 User unknown`),
        contentType: 'message/delivery-status'
      },
      {
        filename: 'original-message.eml',
        content: Buffer.from('From: original-sender@example.com\r\n' +
                           'To: nonexistent@example.com\r\n' +
                           'Subject: Original Subject\r\n\r\n' +
                           'Original message content'),
        contentType: 'message/rfc822'
      }
    ]
  });

  console.log('\nSimulating Non-Delivery Report (NDR)...');
  const result = await smtpClient.sendMail(ndrEmail);
  expect(result).toBeTruthy();
  console.log('NDR sent successfully');

  await smtpClient.close();
});

tap.test('CEP-10: Delivery delay notifications', async () => {
  const smtpClient = createSmtpClient({
    host: testServer.hostname,
    port: testServer.port,
    secure: false,
    connectionTimeout: 5000,
    debug: true
  });

  await smtpClient.connect();

  // Simulate delayed delivery notification
  const delayNotification = new Email({
    from: 'postmaster@example.com',
    to: ['sender@example.com'],
    subject: 'Delivery Status: Delayed',
    headers: {
      'Auto-Submitted': 'auto-replied',
      'Content-Type': 'multipart/report; report-type=delivery-status',
      'X-Delay-Reason': 'Remote server temporarily unavailable'
    },
    text: 'This is an automatically generated Delivery Delay Notification.\n\n' +
          'Your message has not been delivered to the following recipients yet:\n\n' +
          '  recipient@remote-server.com\n\n' +
          'The server will continue trying to deliver your message for 48 hours.',
    attachments: [{
      filename: 'delay-status.txt',
      content: Buffer.from(`Reporting-MTA: dns; mail.example.com
Arrival-Date: ${new Date(Date.now() - 3600000).toUTCString()}
Last-Attempt-Date: ${new Date().toUTCString()}

Final-Recipient: rfc822;recipient@remote-server.com
Action: delayed
Status: 4.4.1
Will-Retry-Until: ${new Date(Date.now() + 172800000).toUTCString()}
Diagnostic-Code: smtp; 421 4.4.1 Remote server temporarily unavailable`),
      contentType: 'message/delivery-status'
    }]
  });

  console.log('\nSimulating Delivery Delay Notification...');
  await smtpClient.sendMail(delayNotification);
  console.log('Delay notification sent successfully');

  await smtpClient.close();
});

tap.test('cleanup test SMTP server', async () => {
  if (testServer) {
    await testServer.stop();
  }
});

export default tap.start();