562 lines
20 KiB
TypeScript
562 lines
20 KiB
TypeScript
import { expect, tap } from '@git.zone/tstest/tapbundle';
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import * as plugins from './plugins.js';
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import { createTestServer } from '../../helpers/server.loader.js';
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import { createSmtpClient } from '../../helpers/smtp.client.js';
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tap.test('CSEC-08: should handle authentication fallback securely', async (tools) => {
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const testId = 'CSEC-08-authentication-fallback';
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console.log(`\n${testId}: Testing authentication fallback mechanisms...`);
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let scenarioCount = 0;
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// Scenario 1: Multiple authentication methods
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await (async () => {
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scenarioCount++;
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console.log(`\nScenario ${scenarioCount}: Testing multiple authentication methods`);
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const testServer = await createTestServer({
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onConnection: async (socket) => {
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console.log(' [Server] Client connected');
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socket.write('220 auth.example.com ESMTP\r\n');
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let authMethod = '';
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let authStep = 0;
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socket.on('data', (data) => {
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const command = data.toString().trim();
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console.log(` [Server] Received: ${command}`);
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if (command.startsWith('EHLO')) {
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socket.write('250-auth.example.com\r\n');
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socket.write('250-AUTH CRAM-MD5 PLAIN LOGIN\r\n');
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socket.write('250 OK\r\n');
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} else if (command.startsWith('AUTH CRAM-MD5')) {
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authMethod = 'CRAM-MD5';
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authStep = 1;
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// Send challenge
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const challenge = Buffer.from(`<${Date.now()}.${Math.random()}@auth.example.com>`).toString('base64');
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socket.write(`334 ${challenge}\r\n`);
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} else if (command.startsWith('AUTH PLAIN')) {
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authMethod = 'PLAIN';
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if (command.length > 11) {
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// Credentials included
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const credentials = Buffer.from(command.substring(11), 'base64').toString();
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console.log(` [Server] PLAIN auth attempt with immediate credentials`);
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socket.write('235 2.7.0 Authentication successful\r\n');
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} else {
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// Request credentials
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socket.write('334\r\n');
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}
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} else if (command.startsWith('AUTH LOGIN')) {
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authMethod = 'LOGIN';
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authStep = 1;
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socket.write('334 VXNlcm5hbWU6\r\n'); // Username:
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} else if (authMethod === 'CRAM-MD5' && authStep === 1) {
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// Verify CRAM-MD5 response
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console.log(` [Server] CRAM-MD5 response received`);
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socket.write('235 2.7.0 Authentication successful\r\n');
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authMethod = '';
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authStep = 0;
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} else if (authMethod === 'PLAIN' && !command.startsWith('AUTH')) {
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// PLAIN credentials
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const credentials = Buffer.from(command, 'base64').toString();
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console.log(` [Server] PLAIN credentials received`);
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socket.write('235 2.7.0 Authentication successful\r\n');
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authMethod = '';
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} else if (authMethod === 'LOGIN' && authStep === 1) {
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// Username
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console.log(` [Server] LOGIN username received`);
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authStep = 2;
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socket.write('334 UGFzc3dvcmQ6\r\n'); // Password:
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} else if (authMethod === 'LOGIN' && authStep === 2) {
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// Password
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console.log(` [Server] LOGIN password received`);
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socket.write('235 2.7.0 Authentication successful\r\n');
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authMethod = '';
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authStep = 0;
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} else if (command.startsWith('MAIL FROM:')) {
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socket.write('250 OK\r\n');
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} else if (command.startsWith('RCPT TO:')) {
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socket.write('250 OK\r\n');
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} else if (command === 'DATA') {
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socket.write('354 Start mail input\r\n');
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} else if (command === '.') {
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socket.write('250 OK\r\n');
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} else if (command === 'QUIT') {
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socket.write('221 Bye\r\n');
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socket.end();
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}
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});
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}
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});
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const smtpClient = createSmtpClient({
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host: testServer.hostname,
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port: testServer.port,
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secure: false,
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auth: {
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user: 'testuser',
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pass: 'testpass'
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}
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});
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const email = new plugins.smartmail.Email({
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from: 'sender@example.com',
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to: ['recipient@example.com'],
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subject: 'Multi-auth test',
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text: 'Testing multiple authentication methods'
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});
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const result = await smtpClient.sendMail(email);
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console.log(' Authentication successful');
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expect(result).toBeDefined();
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expect(result.messageId).toBeDefined();
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await testServer.server.close();
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})();
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// Scenario 2: Authentication method downgrade prevention
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await (async () => {
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scenarioCount++;
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console.log(`\nScenario ${scenarioCount}: Testing auth method downgrade prevention`);
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let attemptCount = 0;
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const testServer = await createTestServer({
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onConnection: async (socket) => {
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console.log(' [Server] Client connected');
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socket.write('220 secure.example.com ESMTP\r\n');
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socket.on('data', (data) => {
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const command = data.toString().trim();
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console.log(` [Server] Received: ${command}`);
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if (command.startsWith('EHLO')) {
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attemptCount++;
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if (attemptCount === 1) {
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// First attempt: offer secure methods
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socket.write('250-secure.example.com\r\n');
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socket.write('250-AUTH CRAM-MD5 SCRAM-SHA-256\r\n');
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socket.write('250 OK\r\n');
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} else {
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// Attacker attempt: offer weaker methods
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socket.write('250-secure.example.com\r\n');
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socket.write('250-AUTH PLAIN LOGIN\r\n');
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socket.write('250 OK\r\n');
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}
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} else if (command.startsWith('AUTH CRAM-MD5')) {
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// Simulate failure to force fallback attempt
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socket.write('535 5.7.8 Authentication failed\r\n');
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} else if (command.startsWith('AUTH PLAIN') || command.startsWith('AUTH LOGIN')) {
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console.log(' [Server] Warning: Client using weak auth method');
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socket.write('535 5.7.8 Weak authentication method not allowed\r\n');
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} else if (command === 'QUIT') {
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socket.write('221 Bye\r\n');
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socket.end();
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}
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});
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}
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});
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const smtpClient = createSmtpClient({
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host: testServer.hostname,
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port: testServer.port,
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secure: false,
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auth: {
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user: 'testuser',
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pass: 'testpass'
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},
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authMethod: 'CRAM-MD5' // Prefer secure method
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});
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const email = new plugins.smartmail.Email({
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from: 'sender@example.com',
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to: ['recipient@example.com'],
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subject: 'Downgrade prevention test',
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text: 'Testing authentication downgrade prevention'
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});
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try {
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await smtpClient.sendMail(email);
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console.log(' Unexpected: Authentication succeeded');
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} catch (error) {
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console.log(` Expected: Auth failed - ${error.message}`);
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expect(error.message).toContain('Authentication failed');
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}
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await testServer.server.close();
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})();
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// Scenario 3: OAuth2 fallback
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await (async () => {
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scenarioCount++;
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console.log(`\nScenario ${scenarioCount}: Testing OAuth2 authentication fallback`);
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const testServer = await createTestServer({
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onConnection: async (socket) => {
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console.log(' [Server] Client connected');
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socket.write('220 oauth.example.com ESMTP\r\n');
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socket.on('data', (data) => {
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const command = data.toString().trim();
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console.log(` [Server] Received: ${command.substring(0, 50)}...`);
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if (command.startsWith('EHLO')) {
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socket.write('250-oauth.example.com\r\n');
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socket.write('250-AUTH XOAUTH2 PLAIN LOGIN\r\n');
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socket.write('250 OK\r\n');
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} else if (command.startsWith('AUTH XOAUTH2')) {
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// Check OAuth2 token
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const token = command.substring(13);
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if (token.includes('expired')) {
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console.log(' [Server] OAuth2 token expired');
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socket.write('334 eyJzdGF0dXMiOiI0MDEiLCJzY2hlbWVzIjoiYmVhcmVyIiwic2NvcGUiOiJodHRwczovL21haWwuZ29vZ2xlLmNvbS8ifQ==\r\n');
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} else {
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console.log(' [Server] OAuth2 authentication successful');
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socket.write('235 2.7.0 Authentication successful\r\n');
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}
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} else if (command.startsWith('AUTH PLAIN')) {
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// Fallback to PLAIN auth
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console.log(' [Server] Fallback to PLAIN auth');
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if (command.length > 11) {
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socket.write('235 2.7.0 Authentication successful\r\n');
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} else {
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socket.write('334\r\n');
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}
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} else if (command === '') {
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// Empty line after failed XOAUTH2
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socket.write('535 5.7.8 Authentication failed\r\n');
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} else if (!command.startsWith('AUTH') && command.length > 20) {
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// PLAIN credentials
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socket.write('235 2.7.0 Authentication successful\r\n');
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} else if (command.startsWith('MAIL FROM:')) {
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socket.write('250 OK\r\n');
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} else if (command.startsWith('RCPT TO:')) {
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socket.write('250 OK\r\n');
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} else if (command === 'DATA') {
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socket.write('354 Start mail input\r\n');
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} else if (command === '.') {
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socket.write('250 OK\r\n');
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} else if (command === 'QUIT') {
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socket.write('221 Bye\r\n');
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socket.end();
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}
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});
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}
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});
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// Test with OAuth2 token
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const oauthClient = createSmtpClient({
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host: testServer.hostname,
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port: testServer.port,
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secure: false,
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auth: {
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type: 'oauth2',
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user: 'user@example.com',
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accessToken: 'valid-oauth-token'
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}
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});
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const email = new plugins.smartmail.Email({
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from: 'sender@example.com',
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to: ['recipient@example.com'],
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subject: 'OAuth2 test',
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text: 'Testing OAuth2 authentication'
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});
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try {
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const result = await oauthClient.sendMail(email);
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console.log(' OAuth2 authentication successful');
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expect(result).toBeDefined();
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} catch (error) {
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console.log(` OAuth2 failed, testing fallback...`);
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// Test fallback to password auth
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const fallbackClient = createSmtpClient({
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host: testServer.hostname,
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port: testServer.port,
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secure: false,
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auth: {
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user: 'testuser',
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pass: 'testpass'
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}
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});
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const result = await fallbackClient.sendMail(email);
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console.log(' Fallback authentication successful');
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expect(result).toBeDefined();
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}
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await testServer.server.close();
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})();
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// Scenario 4: Authentication retry with different credentials
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await (async () => {
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scenarioCount++;
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console.log(`\nScenario ${scenarioCount}: Testing auth retry with different credentials`);
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let authAttempts = 0;
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const testServer = await createTestServer({
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onConnection: async (socket) => {
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console.log(' [Server] Client connected');
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socket.write('220 retry.example.com ESMTP\r\n');
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socket.on('data', (data) => {
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const command = data.toString().trim();
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if (command.startsWith('EHLO')) {
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socket.write('250-retry.example.com\r\n');
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socket.write('250-AUTH PLAIN LOGIN\r\n');
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socket.write('250 OK\r\n');
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} else if (command.startsWith('AUTH')) {
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authAttempts++;
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console.log(` [Server] Auth attempt ${authAttempts}`);
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if (authAttempts <= 2) {
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// Fail first attempts
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socket.write('535 5.7.8 Authentication failed\r\n');
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} else {
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// Success on third attempt
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socket.write('235 2.7.0 Authentication successful\r\n');
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}
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} else if (command.startsWith('MAIL FROM:')) {
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socket.write('250 OK\r\n');
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} else if (command.startsWith('RCPT TO:')) {
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socket.write('250 OK\r\n');
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} else if (command === 'DATA') {
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socket.write('354 Start mail input\r\n');
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} else if (command === '.') {
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socket.write('250 OK\r\n');
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} else if (command === 'QUIT') {
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socket.write('221 Bye\r\n');
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socket.end();
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}
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});
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}
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});
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// Test multiple auth attempts
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const credentials = [
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{ user: 'wronguser', pass: 'wrongpass' },
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{ user: 'testuser', pass: 'wrongpass' },
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{ user: 'testuser', pass: 'testpass' }
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];
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let successfulAuth = false;
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for (const cred of credentials) {
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try {
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const smtpClient = createSmtpClient({
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host: testServer.hostname,
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port: testServer.port,
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secure: false,
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auth: cred
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});
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const email = new plugins.smartmail.Email({
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from: 'sender@example.com',
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to: ['recipient@example.com'],
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subject: 'Retry test',
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text: 'Testing authentication retry'
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});
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const result = await smtpClient.sendMail(email);
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console.log(` Auth succeeded with user: ${cred.user}`);
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successfulAuth = true;
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expect(result).toBeDefined();
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break;
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} catch (error) {
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console.log(` Auth failed with user: ${cred.user}`);
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}
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}
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expect(successfulAuth).toBe(true);
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expect(authAttempts).toBe(3);
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await testServer.server.close();
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})();
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// Scenario 5: Secure authentication over insecure connection
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await (async () => {
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scenarioCount++;
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console.log(`\nScenario ${scenarioCount}: Testing secure auth over insecure connection`);
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const testServer = await createTestServer({
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secure: false, // Plain text connection
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onConnection: async (socket) => {
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console.log(' [Server] Client connected (insecure)');
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socket.write('220 insecure.example.com ESMTP\r\n');
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let tlsStarted = false;
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socket.on('data', (data) => {
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const command = data.toString().trim();
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console.log(` [Server] Received: ${command}`);
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if (command.startsWith('EHLO')) {
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socket.write('250-insecure.example.com\r\n');
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socket.write('250-STARTTLS\r\n');
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if (tlsStarted) {
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socket.write('250-AUTH PLAIN LOGIN\r\n');
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}
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socket.write('250 OK\r\n');
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} else if (command === 'STARTTLS') {
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socket.write('220 2.0.0 Ready to start TLS\r\n');
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tlsStarted = true;
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// In real scenario, would upgrade to TLS here
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} else if (command.startsWith('AUTH') && !tlsStarted) {
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console.log(' [Server] Rejecting auth over insecure connection');
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socket.write('530 5.7.0 Must issue a STARTTLS command first\r\n');
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} else if (command.startsWith('AUTH') && tlsStarted) {
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console.log(' [Server] Accepting auth over TLS');
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socket.write('235 2.7.0 Authentication successful\r\n');
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} else if (command.startsWith('MAIL FROM:')) {
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socket.write('250 OK\r\n');
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} else if (command.startsWith('RCPT TO:')) {
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socket.write('250 OK\r\n');
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} else if (command === 'DATA') {
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socket.write('354 Start mail input\r\n');
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} else if (command === '.') {
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socket.write('250 OK\r\n');
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} else if (command === 'QUIT') {
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socket.write('221 Bye\r\n');
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socket.end();
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}
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});
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}
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});
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// Try auth without TLS (should fail)
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const insecureClient = createSmtpClient({
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host: testServer.hostname,
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port: testServer.port,
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secure: false,
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ignoreTLS: true, // Don't use STARTTLS
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auth: {
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user: 'testuser',
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pass: 'testpass'
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}
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});
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const email = new plugins.smartmail.Email({
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from: 'sender@example.com',
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to: ['recipient@example.com'],
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subject: 'Secure auth test',
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text: 'Testing secure authentication requirements'
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});
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try {
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await insecureClient.sendMail(email);
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console.log(' Unexpected: Auth succeeded without TLS');
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} catch (error) {
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console.log(' Expected: Auth rejected without TLS');
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expect(error.message).toContain('STARTTLS');
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}
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// Try with STARTTLS
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const secureClient = createSmtpClient({
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host: testServer.hostname,
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port: testServer.port,
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secure: false,
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requireTLS: true,
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auth: {
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user: 'testuser',
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pass: 'testpass'
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}
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});
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try {
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const result = await secureClient.sendMail(email);
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console.log(' Auth succeeded with STARTTLS');
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// Note: In real test, STARTTLS would actually upgrade the connection
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} catch (error) {
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console.log(' STARTTLS not fully implemented in test');
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}
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await testServer.server.close();
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})();
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// Scenario 6: Authentication mechanism negotiation
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await (async () => {
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scenarioCount++;
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console.log(`\nScenario ${scenarioCount}: Testing auth mechanism negotiation`);
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const supportedMechanisms = new Map([
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['SCRAM-SHA-256', { priority: 1, supported: true }],
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['CRAM-MD5', { priority: 2, supported: true }],
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['PLAIN', { priority: 3, supported: true }],
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['LOGIN', { priority: 4, supported: true }]
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]);
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const testServer = await createTestServer({
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onConnection: async (socket) => {
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console.log(' [Server] Client connected');
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socket.write('220 negotiate.example.com ESMTP\r\n');
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socket.on('data', (data) => {
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const command = data.toString().trim();
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if (command.startsWith('EHLO')) {
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socket.write('250-negotiate.example.com\r\n');
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const authMechs = Array.from(supportedMechanisms.entries())
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|
.filter(([_, info]) => info.supported)
|
|
.map(([mech, _]) => mech)
|
|
.join(' ');
|
|
socket.write(`250-AUTH ${authMechs}\r\n`);
|
|
socket.write('250 OK\r\n');
|
|
} else if (command.startsWith('AUTH ')) {
|
|
const mechanism = command.split(' ')[1];
|
|
console.log(` [Server] Client selected: ${mechanism}`);
|
|
|
|
const mechInfo = supportedMechanisms.get(mechanism);
|
|
if (mechInfo && mechInfo.supported) {
|
|
console.log(` [Server] Priority: ${mechInfo.priority}`);
|
|
socket.write('235 2.7.0 Authentication successful\r\n');
|
|
} else {
|
|
socket.write('504 5.5.4 Unrecognized authentication type\r\n');
|
|
}
|
|
} else if (command.startsWith('MAIL FROM:')) {
|
|
socket.write('250 OK\r\n');
|
|
} else if (command.startsWith('RCPT TO:')) {
|
|
socket.write('250 OK\r\n');
|
|
} else if (command === 'DATA') {
|
|
socket.write('354 Start mail input\r\n');
|
|
} else if (command === '.') {
|
|
socket.write('250 OK\r\n');
|
|
} else if (command === 'QUIT') {
|
|
socket.write('221 Bye\r\n');
|
|
socket.end();
|
|
}
|
|
});
|
|
}
|
|
});
|
|
|
|
const smtpClient = createSmtpClient({
|
|
host: testServer.hostname,
|
|
port: testServer.port,
|
|
secure: false,
|
|
auth: {
|
|
user: 'testuser',
|
|
pass: 'testpass'
|
|
}
|
|
// Client will negotiate best available mechanism
|
|
});
|
|
|
|
const email = new plugins.smartmail.Email({
|
|
from: 'sender@example.com',
|
|
to: ['recipient@example.com'],
|
|
subject: 'Negotiation test',
|
|
text: 'Testing authentication mechanism negotiation'
|
|
});
|
|
|
|
const result = await smtpClient.sendMail(email);
|
|
console.log(' Authentication negotiation successful');
|
|
expect(result).toBeDefined();
|
|
expect(result.messageId).toBeDefined();
|
|
|
|
await testServer.server.close();
|
|
})();
|
|
|
|
console.log(`\n${testId}: All ${scenarioCount} authentication fallback scenarios tested ✓`);
|
|
}); |