dcrouter/test/suite/smtpclient_rfc-compliance/test.crfc-07.interoperability.ts

import { expect, tap } from '@git.zone/tstest/tapbundle';
import { createTestServer } from '../../helpers/server.loader.js';
import { createTestSmtpClient } from '../../helpers/smtp.client.js';
import { Email } from '../../../ts/index.js';

tap.test('CRFC-07: should ensure SMTP interoperability (RFC 5321)', async (tools) => {
  const testId = 'CRFC-07-interoperability';
  console.log(`\n${testId}: Testing SMTP interoperability compliance...`);

  let scenarioCount = 0;

  // Scenario 1: Different server implementations compatibility
  await (async () => {
    scenarioCount++;
    console.log(`\nScenario ${scenarioCount}: Testing different server implementations`);
    
    const serverImplementations = [
      {
        name: 'Sendmail-style',
        greeting: '220 mail.example.com ESMTP Sendmail 8.15.2/8.15.2; Date Time',
        ehloResponse: [
          '250-mail.example.com Hello client.example.com [192.168.1.100]',
          '250-ENHANCEDSTATUSCODES',
          '250-PIPELINING',
          '250-8BITMIME',
          '250-SIZE 36700160',
          '250-DSN',
          '250-ETRN',
          '250-DELIVERBY',
          '250 HELP'
        ],
        quirks: { verboseResponses: true, includesTimestamp: true }
      },
      {
        name: 'Postfix-style',
        greeting: '220 mail.example.com ESMTP Postfix',
        ehloResponse: [
          '250-mail.example.com',
          '250-PIPELINING',
          '250-SIZE 10240000',
          '250-VRFY',
          '250-ETRN',
          '250-STARTTLS',
          '250-ENHANCEDSTATUSCODES',
          '250-8BITMIME',
          '250-DSN',
          '250 SMTPUTF8'
        ],
        quirks: { shortResponses: true, strictSyntax: true }
      },
      {
        name: 'Exchange-style',
        greeting: '220 mail.example.com Microsoft ESMTP MAIL Service ready',
        ehloResponse: [
          '250-mail.example.com Hello [192.168.1.100]',
          '250-SIZE 37748736',
          '250-PIPELINING',
          '250-DSN',
          '250-ENHANCEDSTATUSCODES',
          '250-STARTTLS',
          '250-8BITMIME',
          '250-BINARYMIME',
          '250-CHUNKING',
          '250 OK'
        ],
        quirks: { windowsLineEndings: true, detailedErrors: true }
      }
    ];

    for (const impl of serverImplementations) {
      console.log(`\n  Testing with ${impl.name} server...`);
      
      const testServer = await createTestServer({
        onConnection: async (socket) => {
          console.log(`    [${impl.name}] Client connected`);
          socket.write(impl.greeting + '\r\n');
          
          socket.on('data', (data) => {
            const command = data.toString().trim();
            console.log(`    [${impl.name}] Received: ${command}`);
            
            if (command.startsWith('EHLO')) {
              impl.ehloResponse.forEach(line => {
                socket.write(line + '\r\n');
              });
            } else if (command.startsWith('MAIL FROM:')) {
              if (impl.quirks.strictSyntax && !command.includes('<')) {
                socket.write('501 5.5.4 Syntax error in MAIL command\r\n');
              } else {
                const response = impl.quirks.verboseResponses ? 
                  '250 2.1.0 Sender OK' : '250 OK';
                socket.write(response + '\r\n');
              }
            } else if (command.startsWith('RCPT TO:')) {
              const response = impl.quirks.verboseResponses ? 
                '250 2.1.5 Recipient OK' : '250 OK';
              socket.write(response + '\r\n');
            } else if (command === 'DATA') {
              const response = impl.quirks.detailedErrors ? 
                '354 Start mail input; end with <CRLF>.<CRLF>' : 
                '354 Enter message, ending with "." on a line by itself';
              socket.write(response + '\r\n');
            } else if (command === '.') {
              const timestamp = impl.quirks.includesTimestamp ? 
                ` at ${new Date().toISOString()}` : '';
              socket.write(`250 2.0.0 Message accepted for delivery${timestamp}\r\n`);
            } else if (command === 'QUIT') {
              const response = impl.quirks.verboseResponses ? 
                '221 2.0.0 Service closing transmission channel' : 
                '221 Bye';
              socket.write(response + '\r\n');
              socket.end();
            }
          });
        }
      });

      const smtpClient = createTestSmtpClient({
        host: testServer.hostname,
        port: testServer.port,
        secure: false
      });

      const email = new Email({
        from: 'sender@example.com',
        to: ['recipient@example.com'],
        subject: `Interoperability test with ${impl.name}`,
        text: `Testing compatibility with ${impl.name} server implementation`
      });

      const result = await smtpClient.sendMail(email);
      console.log(`    ${impl.name} compatibility: Success`);
      expect(result).toBeDefined();
      expect(result.messageId).toBeDefined();

      await testServer.server.close();
    }
  })();

  // Scenario 2: Character encoding and internationalization
  await (async () => {
    scenarioCount++;
    console.log(`\nScenario ${scenarioCount}: Testing character encoding interoperability`);
    
    const testServer = await createTestServer({
      onConnection: async (socket) => {
        console.log('  [Server] Client connected');
        socket.write('220 international.example.com ESMTP\r\n');
        
        let supportsUTF8 = false;
        
        socket.on('data', (data) => {
          const command = data.toString();
          console.log(`  [Server] Received (${data.length} bytes): ${command.trim()}`);
          
          if (command.startsWith('EHLO')) {
            socket.write('250-international.example.com\r\n');
            socket.write('250-8BITMIME\r\n');
            socket.write('250-SMTPUTF8\r\n');
            socket.write('250 OK\r\n');
            supportsUTF8 = true;
          } else if (command.startsWith('MAIL FROM:')) {
            // Check for non-ASCII characters
            const hasNonASCII = /[^\x00-\x7F]/.test(command);
            const hasUTF8Param = command.includes('SMTPUTF8');
            
            console.log(`  [Server] Non-ASCII: ${hasNonASCII}, UTF8 param: ${hasUTF8Param}`);
            
            if (hasNonASCII && !hasUTF8Param) {
              socket.write('553 5.6.7 Non-ASCII addresses require SMTPUTF8\r\n');
            } else {
              socket.write('250 OK\r\n');
            }
          } else if (command.startsWith('RCPT TO:')) {
            socket.write('250 OK\r\n');
          } else if (command.trim() === 'DATA') {
            socket.write('354 Start mail input\r\n');
          } else if (command.trim() === '.') {
            socket.write('250 OK: International message accepted\r\n');
          } else if (command.trim() === 'QUIT') {
            socket.write('221 Bye\r\n');
            socket.end();
          }
        });
      }
    });

    const smtpClient = createTestSmtpClient({
      host: testServer.hostname,
      port: testServer.port,
      secure: false
    });

    // Test various international character sets
    const internationalTests = [
      {
        desc: 'Latin characters with accents',
        from: 'sénder@éxample.com',
        to: 'récipient@éxample.com',
        subject: 'Tëst with açcénts',
        text: 'Café, naïve, résumé, piñata'
      },
      {
        desc: 'Cyrillic characters',
        from: 'отправитель@пример.com',
        to: 'получатель@пример.com',
        subject: 'Тест с кириллицей',
        text: 'Привет мир! Это тест с русскими буквами.'
      },
      {
        desc: 'Chinese characters',
        from: 'sender@example.com',  // ASCII for compatibility
        to: 'recipient@example.com',
        subject: '测试中文字符',
        text: '你好世界！这是一个中文测试。'
      },
      {
        desc: 'Arabic characters',
        from: 'sender@example.com',
        to: 'recipient@example.com',
        subject: 'اختبار النص العربي',
        text: 'مرحبا بالعالم! هذا اختبار باللغة العربية.'
      },
      {
        desc: 'Emoji and symbols',
        from: 'sender@example.com',
        to: 'recipient@example.com',
        subject: '🎉 Test with emojis 🌟',
        text: 'Hello 👋 World 🌍! Testing emojis: 🚀 📧 ✨'
      }
    ];

    for (const test of internationalTests) {
      console.log(`  Testing: ${test.desc}`);
      
      const email = new Email({
        from: test.from,
        to: [test.to],
        subject: test.subject,
        text: test.text
      });

      try {
        const result = await smtpClient.sendMail(email);
        console.log(`    ${test.desc}: Success`);
        expect(result).toBeDefined();
      } catch (error) {
        console.log(`    ${test.desc}: Failed - ${error.message}`);
        // Some may fail if server doesn't support international addresses
      }
    }

    await testServer.server.close();
  })();

  // Scenario 3: Message format compatibility
  await (async () => {
    scenarioCount++;
    console.log(`\nScenario ${scenarioCount}: Testing message format compatibility`);
    
    const testServer = await createTestServer({
      onConnection: async (socket) => {
        console.log('  [Server] Client connected');
        socket.write('220 formats.example.com ESMTP\r\n');
        
        let inData = false;
        let messageContent = '';
        
        socket.on('data', (data) => {
          if (inData) {
            messageContent += data.toString();
            if (messageContent.includes('\r\n.\r\n')) {
              inData = false;
              
              // Analyze message format
              const headers = messageContent.substring(0, messageContent.indexOf('\r\n\r\n'));
              const body = messageContent.substring(messageContent.indexOf('\r\n\r\n') + 4);
              
              console.log('  [Server] Message analysis:');
              console.log(`    Header count: ${(headers.match(/\r\n/g) || []).length + 1}`);
              console.log(`    Body size: ${body.length} bytes`);
              
              // Check for proper header folding
              const longHeaders = headers.split('\r\n').filter(h => h.length > 78);
              if (longHeaders.length > 0) {
                console.log(`    Long headers detected: ${longHeaders.length}`);
              }
              
              // Check for MIME structure
              if (headers.includes('Content-Type:')) {
                console.log('    MIME message detected');
              }
              
              socket.write('250 OK: Message format validated\r\n');
              messageContent = '';
            }
            return;
          }
          
          const command = data.toString().trim();
          console.log(`  [Server] Received: ${command}`);
          
          if (command.startsWith('EHLO')) {
            socket.write('250-formats.example.com\r\n');
            socket.write('250-8BITMIME\r\n');
            socket.write('250-BINARYMIME\r\n');
            socket.write('250 SIZE 52428800\r\n');
          } else if (command.startsWith('MAIL FROM:')) {
            socket.write('250 OK\r\n');
          } else if (command.startsWith('RCPT TO:')) {
            socket.write('250 OK\r\n');
          } else if (command === 'DATA') {
            socket.write('354 Start mail input\r\n');
            inData = true;
          } else if (command === 'QUIT') {
            socket.write('221 Bye\r\n');
            socket.end();
          }
        });
      }
    });

    const smtpClient = createTestSmtpClient({
      host: testServer.hostname,
      port: testServer.port,
      secure: false
    });

    // Test different message formats
    const formatTests = [
      {
        desc: 'Plain text message',
        email: new Email({
          from: 'sender@example.com',
          to: ['recipient@example.com'],
          subject: 'Plain text test',
          text: 'This is a simple plain text message.'
        })
      },
      {
        desc: 'HTML message',
        email: new Email({
          from: 'sender@example.com',
          to: ['recipient@example.com'],
          subject: 'HTML test',
          html: '<h1>HTML Message</h1><p>This is an <strong>HTML</strong> message.</p>'
        })
      },
      {
        desc: 'Multipart alternative',
        email: new Email({
          from: 'sender@example.com',
          to: ['recipient@example.com'],
          subject: 'Multipart test',
          text: 'Plain text version',
          html: '<p>HTML version</p>'
        })
      },
      {
        desc: 'Message with attachment',
        email: new Email({
          from: 'sender@example.com',
          to: ['recipient@example.com'],
          subject: 'Attachment test',
          text: 'Message with attachment',
          attachments: [{
            filename: 'test.txt',
            content: 'This is a test attachment'
          }]
        })
      },
      {
        desc: 'Message with custom headers',
        email: new Email({
          from: 'sender@example.com',
          to: ['recipient@example.com'],
          subject: 'Custom headers test',
          text: 'Message with custom headers',
          headers: {
            'X-Custom-Header': 'Custom value',
            'X-Mailer': 'Test Mailer 1.0',
            'Message-ID': '<test123@example.com>',
            'References': '<ref1@example.com> <ref2@example.com>'
          }
        })
      }
    ];

    for (const test of formatTests) {
      console.log(`  Testing: ${test.desc}`);
      
      const result = await smtpClient.sendMail(test.email);
      console.log(`    ${test.desc}: Success`);
      expect(result).toBeDefined();
      expect(result.messageId).toBeDefined();
    }

    await testServer.server.close();
  })();

  // Scenario 4: Error handling interoperability
  await (async () => {
    scenarioCount++;
    console.log(`\nScenario ${scenarioCount}: Testing error handling interoperability`);
    
    const testServer = await createTestServer({
      onConnection: async (socket) => {
        console.log('  [Server] Client connected');
        socket.write('220 errors.example.com ESMTP\r\n');
        
        socket.on('data', (data) => {
          const command = data.toString().trim();
          console.log(`  [Server] Received: ${command}`);
          
          if (command.startsWith('EHLO')) {
            socket.write('250-errors.example.com\r\n');
            socket.write('250-ENHANCEDSTATUSCODES\r\n');
            socket.write('250 OK\r\n');
          } else if (command.startsWith('MAIL FROM:')) {
            const address = command.match(/<(.+)>/)?.[1] || '';
            
            if (address.includes('temp-fail')) {
              // Temporary failure - client should retry
              socket.write('451 4.7.1 Temporary system problem, try again later\r\n');
            } else if (address.includes('perm-fail')) {
              // Permanent failure - client should not retry
              socket.write('550 5.1.8 Invalid sender address format\r\n');
            } else if (address.includes('syntax-error')) {
              // Syntax error
              socket.write('501 5.5.4 Syntax error in MAIL command\r\n');
            } else {
              socket.write('250 OK\r\n');
            }
          } else if (command.startsWith('RCPT TO:')) {
            const address = command.match(/<(.+)>/)?.[1] || '';
            
            if (address.includes('unknown')) {
              socket.write('550 5.1.1 User unknown in local recipient table\r\n');
            } else if (address.includes('temp-reject')) {
              socket.write('450 4.2.1 Mailbox temporarily unavailable\r\n');
            } else if (address.includes('quota-exceeded')) {
              socket.write('552 5.2.2 Mailbox over quota\r\n');
            } else {
              socket.write('250 OK\r\n');
            }
          } else if (command === 'DATA') {
            socket.write('354 Start mail input\r\n');
          } else if (command === '.') {
            socket.write('250 OK\r\n');
          } else if (command === 'QUIT') {
            socket.write('221 Bye\r\n');
            socket.end();
          } else {
            // Unknown command
            socket.write('500 5.5.1 Command unrecognized\r\n');
          }
        });
      }
    });

    const smtpClient = createTestSmtpClient({
      host: testServer.hostname,
      port: testServer.port,
      secure: false
    });

    // Test various error scenarios
    const errorTests = [
      {
        desc: 'Temporary sender failure',
        from: 'temp-fail@example.com',
        to: 'valid@example.com',
        expectError: true,
        errorType: '4xx'
      },
      {
        desc: 'Permanent sender failure',
        from: 'perm-fail@example.com',
        to: 'valid@example.com',
        expectError: true,
        errorType: '5xx'
      },
      {
        desc: 'Unknown recipient',
        from: 'valid@example.com',
        to: 'unknown@example.com',
        expectError: true,
        errorType: '5xx'
      },
      {
        desc: 'Mixed valid/invalid recipients',
        from: 'valid@example.com',
        to: ['valid@example.com', 'unknown@example.com', 'temp-reject@example.com'],
        expectError: false,  // Partial success
        errorType: 'mixed'
      }
    ];

    for (const test of errorTests) {
      console.log(`  Testing: ${test.desc}`);
      
      const email = new Email({
        from: test.from,
        to: Array.isArray(test.to) ? test.to : [test.to],
        subject: `Error test: ${test.desc}`,
        text: `Testing error handling for ${test.desc}`
      });

      try {
        const result = await smtpClient.sendMail(email);
        
        if (test.expectError && test.errorType !== 'mixed') {
          console.log(`    Unexpected success for ${test.desc}`);
        } else {
          console.log(`    ${test.desc}: Handled correctly`);
          if (result.rejected && result.rejected.length > 0) {
            console.log(`      Rejected: ${result.rejected.length} recipients`);
          }
          if (result.accepted && result.accepted.length > 0) {
            console.log(`      Accepted: ${result.accepted.length} recipients`);
          }
        }
      } catch (error) {
        if (test.expectError) {
          console.log(`    ${test.desc}: Failed as expected (${error.responseCode})`);
          if (test.errorType === '4xx') {
            expect(error.responseCode).toBeGreaterThanOrEqual(400);
            expect(error.responseCode).toBeLessThan(500);
          } else if (test.errorType === '5xx') {
            expect(error.responseCode).toBeGreaterThanOrEqual(500);
            expect(error.responseCode).toBeLessThan(600);
          }
        } else {
          console.log(`    Unexpected error for ${test.desc}: ${error.message}`);
        }
      }
    }

    await testServer.server.close();
  })();

  // Scenario 5: Connection management interoperability
  await (async () => {
    scenarioCount++;
    console.log(`\nScenario ${scenarioCount}: Testing connection management interoperability`);
    
    const testServer = await createTestServer({
      onConnection: async (socket) => {
        console.log('  [Server] Client connected');
        
        let commandCount = 0;
        let idleTime = Date.now();
        const maxIdleTime = 5000;  // 5 seconds for testing
        const maxCommands = 10;
        
        socket.write('220 connection.example.com ESMTP\r\n');
        
        // Set up idle timeout
        const idleCheck = setInterval(() => {
          if (Date.now() - idleTime > maxIdleTime) {
            console.log('  [Server] Idle timeout - closing connection');
            socket.write('421 4.4.2 Idle timeout, closing connection\r\n');
            socket.end();
            clearInterval(idleCheck);
          }
        }, 1000);
        
        socket.on('data', (data) => {
          const command = data.toString().trim();
          commandCount++;
          idleTime = Date.now();
          
          console.log(`  [Server] Command ${commandCount}: ${command}`);
          
          if (commandCount > maxCommands) {
            console.log('  [Server] Too many commands - closing connection');
            socket.write('421 4.7.0 Too many commands, closing connection\r\n');
            socket.end();
            clearInterval(idleCheck);
            return;
          }
          
          if (command.startsWith('EHLO')) {
            socket.write('250-connection.example.com\r\n');
            socket.write('250-PIPELINING\r\n');
            socket.write('250 OK\r\n');
          } else if (command.startsWith('MAIL FROM:')) {
            socket.write('250 OK\r\n');
          } else if (command.startsWith('RCPT TO:')) {
            socket.write('250 OK\r\n');
          } else if (command === 'DATA') {
            socket.write('354 Start mail input\r\n');
          } else if (command === '.') {
            socket.write('250 OK\r\n');
          } else if (command === 'RSET') {
            socket.write('250 OK\r\n');
          } else if (command === 'NOOP') {
            socket.write('250 OK\r\n');
          } else if (command === 'QUIT') {
            socket.write('221 Bye\r\n');
            socket.end();
            clearInterval(idleCheck);
          }
        });
        
        socket.on('close', () => {
          clearInterval(idleCheck);
          console.log(`  [Server] Connection closed after ${commandCount} commands`);
        });
      }
    });

    const smtpClient = createTestSmtpClient({
      host: testServer.hostname,
      port: testServer.port,
      secure: false,
      pool: true,
      maxConnections: 1
    });

    // Test connection reuse
    console.log('  Testing connection reuse...');
    
    for (let i = 1; i <= 3; i++) {
      const email = new Email({
        from: 'sender@example.com',
        to: [`recipient${i}@example.com`],
        subject: `Connection test ${i}`,
        text: `Testing connection management - email ${i}`
      });

      const result = await smtpClient.sendMail(email);
      console.log(`    Email ${i} sent successfully`);
      expect(result).toBeDefined();
      
      // Small delay to test connection persistence
      await new Promise(resolve => setTimeout(resolve, 500));
    }

    // Test NOOP for keeping connection alive
    console.log('  Testing connection keep-alive...');
    
    await smtpClient.verify();  // This might send NOOP
    console.log('    Connection verified (keep-alive)');

    await smtpClient.close();
    await testServer.server.close();
  })();

  // Scenario 6: Legacy SMTP compatibility
  await (async () => {
    scenarioCount++;
    console.log(`\nScenario ${scenarioCount}: Testing legacy SMTP compatibility`);
    
    const testServer = await createTestServer({
      onConnection: async (socket) => {
        console.log('  [Server] Legacy SMTP server');
        
        // Old-style greeting without ESMTP
        socket.write('220 legacy.example.com Simple Mail Transfer Service Ready\r\n');
        
        socket.on('data', (data) => {
          const command = data.toString().trim();
          console.log(`  [Server] Received: ${command}`);
          
          if (command.startsWith('EHLO')) {
            // Legacy server doesn't understand EHLO
            socket.write('500 Command unrecognized\r\n');
          } else if (command.startsWith('HELO')) {
            socket.write('250 legacy.example.com\r\n');
          } else if (command.startsWith('MAIL FROM:')) {
            // Very strict syntax checking
            if (!command.match(/^MAIL FROM:\s*<[^>]+>\s*$/)) {
              socket.write('501 Syntax error\r\n');
            } else {
              socket.write('250 Sender OK\r\n');
            }
          } else if (command.startsWith('RCPT TO:')) {
            if (!command.match(/^RCPT TO:\s*<[^>]+>\s*$/)) {
              socket.write('501 Syntax error\r\n');
            } else {
              socket.write('250 Recipient OK\r\n');
            }
          } else if (command === 'DATA') {
            socket.write('354 Enter mail, end with "." on a line by itself\r\n');
          } else if (command === '.') {
            socket.write('250 Message accepted for delivery\r\n');
          } else if (command === 'QUIT') {
            socket.write('221 Service closing transmission channel\r\n');
            socket.end();
          } else if (command === 'HELP') {
            socket.write('214-Commands supported:\r\n');
            socket.write('214-HELO MAIL RCPT DATA QUIT HELP\r\n');
            socket.write('214 End of HELP info\r\n');
          } else {
            socket.write('500 Command unrecognized\r\n');
          }
        });
      }
    });

    // Test with client that can fall back to basic SMTP
    const legacyClient = createTestSmtpClient({
      host: testServer.hostname,
      port: testServer.port,
      secure: false,
      disableESMTP: true  // Force HELO mode
    });

    const email = new Email({
      from: 'sender@example.com',
      to: ['recipient@example.com'],
      subject: 'Legacy compatibility test',
      text: 'Testing compatibility with legacy SMTP servers'
    });

    const result = await legacyClient.sendMail(email);
    console.log('  Legacy SMTP compatibility: Success');
    expect(result).toBeDefined();
    expect(result.messageId).toBeDefined();

    await testServer.server.close();
  })();

  console.log(`\n${testId}: All ${scenarioCount} interoperability scenarios tested ✓`);
});

tap.start();