update

test/suite/smtpclient_connection/test.ccm-03.starttls-upgrade.ts

@@ -0,0 +1,200 @@
+import { tap, expect } from '@git.zone/tstest/tapbundle';
+import { startTestServer, stopTestServer, type ITestServer } from '../../helpers/server.loader.js';
+import { createSmtpClient } from '../../../ts/mail/delivery/smtpclient/index.js';
+import type { SmtpClient } from '../../../ts/mail/delivery/smtpclient/smtp-client.js';
+import { Email } from '../../../ts/mail/core/classes.email.js';
+
+let testServer: ITestServer;
+let smtpClient: SmtpClient;
+
+tap.test('setup - start SMTP server with STARTTLS support', async () => {
+  testServer = await startTestServer({
+    port: 2528,
+    tlsEnabled: true, // Enables STARTTLS capability
+    authRequired: false
+  });
+  
+  expect(testServer.port).toEqual(2528);
+});
+
+tap.test('CCM-03: STARTTLS Upgrade - should upgrade plain connection to TLS', async () => {
+  const startTime = Date.now();
+  
+  try {
+    // Create SMTP client starting with plain connection
+    smtpClient = createSmtpClient({
+      host: testServer.hostname,
+      port: testServer.port,
+      secure: false, // Start with plain connection
+      connectionTimeout: 10000,
+      tls: {
+        rejectUnauthorized: false // For self-signed test certificates
+      },
+      debug: true
+    });
+    
+    // The client should automatically upgrade to TLS via STARTTLS
+    const isConnected = await smtpClient.verify();
+    expect(isConnected).toBeTrue();
+    
+    const duration = Date.now() - startTime;
+    console.log(`✅ STARTTLS upgrade completed in ${duration}ms`);
+    
+  } catch (error) {
+    const duration = Date.now() - startTime;
+    console.error(`❌ STARTTLS upgrade failed after ${duration}ms:`, error);
+    throw error;
+  }
+});
+
+tap.test('CCM-03: STARTTLS Upgrade - should send email after upgrade', async () => {
+  const email = new Email({
+    from: 'test@example.com',
+    to: 'recipient@example.com',
+    subject: 'STARTTLS Upgrade Test',
+    text: 'This email was sent after STARTTLS upgrade',
+    html: '<p>This email was sent after <strong>STARTTLS upgrade</strong></p>'
+  });
+  
+  const result = await smtpClient.sendMail(email);
+  
+  expect(result.success).toBeTrue();
+  expect(result.acceptedRecipients).toContain('recipient@example.com');
+  expect(result.rejectedRecipients.length).toEqual(0);
+  
+  console.log('✅ Email sent successfully after STARTTLS upgrade');
+  console.log('📧 Message ID:', result.messageId);
+});
+
+tap.test('CCM-03: STARTTLS Upgrade - should handle servers without STARTTLS', async () => {
+  // Start a server without TLS support
+  const plainServer = await startTestServer({
+    port: 2529,
+    tlsEnabled: false // No STARTTLS support
+  });
+  
+  try {
+    const plainClient = createSmtpClient({
+      host: plainServer.hostname,
+      port: plainServer.port,
+      secure: false,
+      connectionTimeout: 5000,
+      debug: true
+    });
+    
+    // Should still connect but without TLS
+    const isConnected = await plainClient.verify();
+    expect(isConnected).toBeTrue();
+    
+    // Send test email over plain connection
+    const email = new Email({
+      from: 'test@example.com',
+      to: 'recipient@example.com',
+      subject: 'Plain Connection Test',
+      text: 'This email was sent over plain connection'
+    });
+    
+    const result = await plainClient.sendMail(email);
+    expect(result.success).toBeTrue();
+    
+    await plainClient.close();
+    console.log('✅ Successfully handled server without STARTTLS');
+    
+  } finally {
+    await stopTestServer(plainServer);
+  }
+});
+
+tap.test('CCM-03: STARTTLS Upgrade - should respect TLS options during upgrade', async () => {
+  const customTlsClient = createSmtpClient({
+    host: testServer.hostname,
+    port: testServer.port,
+    secure: false, // Start plain
+    connectionTimeout: 10000,
+    tls: {
+      rejectUnauthorized: false,
+      minVersion: 'TLSv1.2',
+      ciphers: 'HIGH:!aNULL:!MD5'
+    }
+  });
+  
+  const isConnected = await customTlsClient.verify();
+  expect(isConnected).toBeTrue();
+  
+  await customTlsClient.close();
+  console.log('✅ Custom TLS options applied during STARTTLS upgrade');
+});
+
+tap.test('CCM-03: STARTTLS Upgrade - should handle upgrade failures gracefully', async () => {
+  // Create a mock scenario where STARTTLS might fail
+  // This would typically happen with certificate issues or protocol mismatches
+  
+  let errorCaught = false;
+  
+  try {
+    const strictTlsClient = createSmtpClient({
+      host: testServer.hostname,
+      port: testServer.port,
+      secure: false,
+      connectionTimeout: 5000,
+      tls: {
+        rejectUnauthorized: true, // Strict validation with self-signed cert
+        servername: 'wrong.hostname.com' // Wrong hostname
+      }
+    });
+    
+    await strictTlsClient.verify();
+    await strictTlsClient.close();
+  } catch (error) {
+    errorCaught = true;
+    expect(error).toBeInstanceOf(Error);
+    console.log('✅ STARTTLS upgrade failure handled gracefully');
+  }
+  
+  // Should fail due to certificate validation
+  expect(errorCaught).toBeTrue();
+});
+
+tap.test('CCM-03: STARTTLS Upgrade - should maintain connection state after upgrade', async () => {
+  const stateClient = createSmtpClient({
+    host: testServer.hostname,
+    port: testServer.port,
+    secure: false,
+    connectionTimeout: 10000,
+    tls: {
+      rejectUnauthorized: false
+    }
+  });
+  
+  // Connect and verify
+  await stateClient.verify();
+  expect(stateClient.isConnected()).toBeTrue();
+  
+  // Send multiple emails to verify connection remains stable
+  for (let i = 0; i < 3; i++) {
+    const email = new Email({
+      from: 'test@example.com',
+      to: 'recipient@example.com',
+      subject: `STARTTLS State Test ${i + 1}`,
+      text: `Message ${i + 1} after STARTTLS upgrade`
+    });
+    
+    const result = await stateClient.sendMail(email);
+    expect(result.success).toBeTrue();
+  }
+  
+  await stateClient.close();
+  console.log('✅ Connection state maintained after STARTTLS upgrade');
+});
+
+tap.test('cleanup - close SMTP client', async () => {
+  if (smtpClient && smtpClient.isConnected()) {
+    await smtpClient.close();
+  }
+});
+
+tap.test('cleanup - stop SMTP server', async () => {
+  await stopTestServer(testServer);
+});
+
+tap.start();