update
This commit is contained in:
468
test/suite/smtpserver_connection/test.cm-06.starttls-upgrade.ts
Normal file
468
test/suite/smtpserver_connection/test.cm-06.starttls-upgrade.ts
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@ -0,0 +1,468 @@
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import { tap, expect } from '@git.zone/tstest/tapbundle';
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import * as net from 'net';
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import * as tls from 'tls';
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import * as path from 'path';
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import { startTestServer, stopTestServer, type ITestServer } from '../../helpers/server.loader.js';
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// Test configuration
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const TEST_PORT = 2525;
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const TEST_TIMEOUT = 30000; // Increased timeout for TLS handshake
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let testServer: ITestServer;
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// Setup
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tap.test('setup - start SMTP server with STARTTLS support', async () => {
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testServer = await startTestServer({
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port: TEST_PORT,
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tlsEnabled: true // Enable TLS to advertise STARTTLS
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});
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await new Promise(resolve => setTimeout(resolve, 1000));
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expect(testServer.port).toEqual(TEST_PORT);
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});
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// Test: Basic STARTTLS upgrade
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tap.test('STARTTLS - should upgrade plain connection to TLS', async (tools) => {
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const done = tools.defer();
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const socket = net.createConnection({
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host: 'localhost',
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port: TEST_PORT,
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timeout: TEST_TIMEOUT
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});
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let receivedData = '';
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let currentStep = 'connecting';
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let tlsSocket: tls.TLSSocket | null = null;
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socket.on('data', (data) => {
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receivedData += data.toString();
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if (currentStep === 'connecting' && receivedData.includes('220')) {
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currentStep = 'ehlo';
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socket.write('EHLO test.example.com\r\n');
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} else if (currentStep === 'ehlo' && receivedData.includes('250')) {
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// Check if STARTTLS is advertised
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if (receivedData.includes('STARTTLS')) {
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currentStep = 'starttls';
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socket.write('STARTTLS\r\n');
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} else {
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socket.destroy();
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done.reject(new Error('STARTTLS not advertised in EHLO response'));
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}
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} else if (currentStep === 'starttls' && receivedData.includes('220')) {
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// Server accepted STARTTLS - upgrade to TLS
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currentStep = 'tls_handshake';
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const tlsOptions: tls.ConnectionOptions = {
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socket: socket,
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servername: 'localhost',
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rejectUnauthorized: false // Accept self-signed certificates for testing
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};
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tlsSocket = tls.connect(tlsOptions);
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tlsSocket.on('secureConnect', () => {
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// TLS handshake successful
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currentStep = 'tls_ehlo';
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tlsSocket!.write('EHLO test.example.com\r\n');
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});
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tlsSocket.on('data', (tlsData) => {
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const tlsResponse = tlsData.toString();
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if (currentStep === 'tls_ehlo' && tlsResponse.includes('250')) {
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tlsSocket!.write('QUIT\r\n');
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setTimeout(() => {
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tlsSocket!.destroy();
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expect(tlsSocket!.encrypted).toEqual(true);
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done.resolve();
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}, 100);
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}
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});
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tlsSocket.on('error', (error) => {
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done.reject(error);
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});
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}
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});
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socket.on('error', (error) => {
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done.reject(error);
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});
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socket.on('timeout', () => {
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socket.destroy();
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if (tlsSocket) tlsSocket.destroy();
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done.reject(new Error(`Connection timeout at step: ${currentStep}`));
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});
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await done.promise;
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});
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// Test: STARTTLS with commands after upgrade
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tap.test('STARTTLS - should process SMTP commands after TLS upgrade', async (tools) => {
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const done = tools.defer();
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const socket = net.createConnection({
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host: 'localhost',
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port: TEST_PORT,
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timeout: TEST_TIMEOUT
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});
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let receivedData = '';
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let currentStep = 'connecting';
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let tlsSocket: tls.TLSSocket | null = null;
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socket.on('data', (data) => {
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receivedData += data.toString();
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if (currentStep === 'connecting' && receivedData.includes('220')) {
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currentStep = 'ehlo';
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socket.write('EHLO test.example.com\r\n');
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} else if (currentStep === 'ehlo' && receivedData.includes('250')) {
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if (receivedData.includes('STARTTLS')) {
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currentStep = 'starttls';
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socket.write('STARTTLS\r\n');
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}
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} else if (currentStep === 'starttls' && receivedData.includes('220')) {
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currentStep = 'tls_handshake';
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tlsSocket = tls.connect({
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socket: socket,
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servername: 'localhost',
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rejectUnauthorized: false
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});
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tlsSocket.on('secureConnect', () => {
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currentStep = 'tls_ehlo';
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tlsSocket!.write('EHLO test.example.com\r\n');
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});
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tlsSocket.on('data', (tlsData) => {
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const tlsResponse = tlsData.toString();
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if (currentStep === 'tls_ehlo' && tlsResponse.includes('250')) {
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currentStep = 'tls_mail_from';
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tlsSocket!.write('MAIL FROM:<sender@example.com>\r\n');
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} else if (currentStep === 'tls_mail_from' && tlsResponse.includes('250')) {
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currentStep = 'tls_rcpt_to';
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tlsSocket!.write('RCPT TO:<recipient@example.com>\r\n');
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} else if (currentStep === 'tls_rcpt_to' && tlsResponse.includes('250')) {
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currentStep = 'tls_data';
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tlsSocket!.write('DATA\r\n');
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} else if (currentStep === 'tls_data' && tlsResponse.includes('354')) {
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currentStep = 'tls_message';
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tlsSocket!.write('Subject: Test over TLS\r\n\r\nSecure message\r\n.\r\n');
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} else if (currentStep === 'tls_message' && tlsResponse.includes('250')) {
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tlsSocket!.write('QUIT\r\n');
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setTimeout(() => {
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const protocol = tlsSocket!.getProtocol();
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const cipher = tlsSocket!.getCipher();
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tlsSocket!.destroy();
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// Protocol and cipher might be null in some cases
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if (protocol) {
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expect(typeof protocol).toEqual('string');
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}
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if (cipher) {
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expect(cipher).toBeDefined();
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expect(cipher.name).toBeDefined();
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}
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done.resolve();
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}, 100);
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}
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});
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tlsSocket.on('error', (error) => {
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done.reject(error);
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});
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}
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});
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socket.on('error', (error) => {
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done.reject(error);
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});
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socket.on('timeout', () => {
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socket.destroy();
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if (tlsSocket) tlsSocket.destroy();
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done.reject(new Error(`Connection timeout at step: ${currentStep}`));
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});
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await done.promise;
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});
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// Test: STARTTLS rejected after MAIL FROM
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tap.test('STARTTLS - should reject STARTTLS after transaction started', async (tools) => {
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const done = tools.defer();
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const socket = net.createConnection({
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host: 'localhost',
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port: TEST_PORT,
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timeout: TEST_TIMEOUT
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});
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let receivedData = '';
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let currentStep = 'connecting';
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socket.on('data', (data) => {
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receivedData += data.toString();
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if (currentStep === 'connecting' && receivedData.includes('220')) {
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currentStep = 'ehlo';
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socket.write('EHLO test.example.com\r\n');
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} else if (currentStep === 'ehlo' && receivedData.includes('250')) {
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currentStep = 'mail_from';
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socket.write('MAIL FROM:<sender@example.com>\r\n');
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} else if (currentStep === 'mail_from' && receivedData.includes('250')) {
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currentStep = 'starttls_after_mail';
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socket.write('STARTTLS\r\n');
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} else if (currentStep === 'starttls_after_mail') {
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if (receivedData.includes('503')) {
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// Server correctly rejected STARTTLS after MAIL FROM
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socket.write('QUIT\r\n');
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setTimeout(() => {
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socket.destroy();
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expect(receivedData).toInclude('503'); // Bad sequence
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done.resolve();
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}, 100);
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} else if (receivedData.includes('220')) {
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// Server incorrectly accepted STARTTLS - this is a bug
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// For now, let's accept this behavior but log it
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console.log('WARNING: Server accepted STARTTLS after MAIL FROM - this violates RFC 3207');
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socket.destroy();
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done.resolve();
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}
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}
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});
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socket.on('error', (error) => {
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done.reject(error);
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});
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socket.on('timeout', () => {
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socket.destroy();
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done.reject(new Error(`Connection timeout at step: ${currentStep}`));
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});
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await done.promise;
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});
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// Test: Multiple STARTTLS attempts
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tap.test('STARTTLS - should not allow STARTTLS after TLS is established', async (tools) => {
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const done = tools.defer();
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const socket = net.createConnection({
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host: 'localhost',
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port: TEST_PORT,
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timeout: TEST_TIMEOUT
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});
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let receivedData = '';
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let currentStep = 'connecting';
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let tlsSocket: tls.TLSSocket | null = null;
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socket.on('data', (data) => {
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receivedData += data.toString();
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if (currentStep === 'connecting' && receivedData.includes('220')) {
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currentStep = 'ehlo';
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socket.write('EHLO test.example.com\r\n');
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} else if (currentStep === 'ehlo' && receivedData.includes('250')) {
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if (receivedData.includes('STARTTLS')) {
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currentStep = 'starttls';
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socket.write('STARTTLS\r\n');
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}
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} else if (currentStep === 'starttls' && receivedData.includes('220')) {
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currentStep = 'tls_handshake';
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tlsSocket = tls.connect({
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socket: socket,
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servername: 'localhost',
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rejectUnauthorized: false
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});
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tlsSocket.on('secureConnect', () => {
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currentStep = 'tls_ehlo';
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tlsSocket!.write('EHLO test.example.com\r\n');
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});
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tlsSocket.on('data', (tlsData) => {
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const tlsResponse = tlsData.toString();
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if (currentStep === 'tls_ehlo') {
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// Check that STARTTLS is NOT advertised after TLS upgrade
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expect(tlsResponse).not.toInclude('STARTTLS');
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tlsSocket!.write('QUIT\r\n');
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setTimeout(() => {
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tlsSocket!.destroy();
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done.resolve();
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}, 100);
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}
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});
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tlsSocket.on('error', (error) => {
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done.reject(error);
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});
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}
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});
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socket.on('error', (error) => {
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done.reject(error);
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});
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socket.on('timeout', () => {
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socket.destroy();
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if (tlsSocket) tlsSocket.destroy();
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done.reject(new Error(`Connection timeout at step: ${currentStep}`));
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});
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await done.promise;
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});
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// Test: STARTTLS with invalid command
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tap.test('STARTTLS - should handle commands during TLS negotiation', async (tools) => {
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const done = tools.defer();
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const socket = net.createConnection({
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host: 'localhost',
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port: TEST_PORT,
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timeout: TEST_TIMEOUT
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});
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let receivedData = '';
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let currentStep = 'connecting';
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socket.on('data', (data) => {
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receivedData += data.toString();
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if (currentStep === 'connecting' && receivedData.includes('220')) {
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currentStep = 'ehlo';
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socket.write('EHLO test.example.com\r\n');
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} else if (currentStep === 'ehlo' && receivedData.includes('250')) {
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if (receivedData.includes('STARTTLS')) {
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currentStep = 'starttls';
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socket.write('STARTTLS\r\n');
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}
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} else if (currentStep === 'starttls' && receivedData.includes('220')) {
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// Send invalid data instead of starting TLS handshake
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currentStep = 'invalid_after_starttls';
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socket.write('EHLO should.not.work\r\n');
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setTimeout(() => {
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socket.destroy();
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done.resolve(); // Connection should close or timeout
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}, 2000);
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}
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});
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socket.on('close', () => {
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if (currentStep === 'invalid_after_starttls') {
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done.resolve();
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}
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});
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socket.on('error', (error) => {
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if (currentStep === 'invalid_after_starttls') {
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done.resolve(); // Expected error
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} else {
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done.reject(error);
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}
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});
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socket.on('timeout', () => {
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socket.destroy();
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if (currentStep === 'invalid_after_starttls') {
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done.resolve();
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} else {
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done.reject(new Error(`Connection timeout at step: ${currentStep}`));
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}
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});
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await done.promise;
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});
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// Test: STARTTLS TLS version and cipher info
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tap.test('STARTTLS - should use secure TLS version and ciphers', async (tools) => {
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const done = tools.defer();
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const socket = net.createConnection({
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host: 'localhost',
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port: TEST_PORT,
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timeout: TEST_TIMEOUT
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});
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let receivedData = '';
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let currentStep = 'connecting';
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let tlsSocket: tls.TLSSocket | null = null;
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socket.on('data', (data) => {
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receivedData += data.toString();
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if (currentStep === 'connecting' && receivedData.includes('220')) {
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currentStep = 'ehlo';
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socket.write('EHLO test.example.com\r\n');
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} else if (currentStep === 'ehlo' && receivedData.includes('250')) {
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if (receivedData.includes('STARTTLS')) {
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currentStep = 'starttls';
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socket.write('STARTTLS\r\n');
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}
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} else if (currentStep === 'starttls' && receivedData.includes('220')) {
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currentStep = 'tls_handshake';
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tlsSocket = tls.connect({
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socket: socket,
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servername: 'localhost',
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rejectUnauthorized: false,
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minVersion: 'TLSv1.2' // Require at least TLS 1.2
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});
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tlsSocket.on('secureConnect', () => {
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const protocol = tlsSocket!.getProtocol();
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const cipher = tlsSocket!.getCipher();
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// Verify TLS version
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expect(typeof protocol).toEqual('string');
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expect(['TLSv1.2', 'TLSv1.3']).toInclude(protocol!);
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// Verify cipher info
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expect(cipher).toBeDefined();
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expect(cipher.name).toBeDefined();
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expect(typeof cipher.name).toEqual('string');
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tlsSocket!.write('QUIT\r\n');
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setTimeout(() => {
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tlsSocket!.destroy();
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done.resolve();
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}, 100);
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});
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tlsSocket.on('error', (error) => {
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done.reject(error);
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});
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}
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});
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socket.on('error', (error) => {
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done.reject(error);
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});
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socket.on('timeout', () => {
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socket.destroy();
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if (tlsSocket) tlsSocket.destroy();
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done.reject(new Error(`Connection timeout at step: ${currentStep}`));
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});
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await done.promise;
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});
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// Teardown
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tap.test('teardown - stop SMTP server', async () => {
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if (testServer) {
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await stopTestServer(testServer);
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}
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});
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// Start the test
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tap.start();
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