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update

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This commit is contained in:
Philipp Kunz
2025-05-24 00:23:35 +00:00
parent 0907949f8a
commit cb52446f65
76 changed files with 1401 additions and 867 deletions
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322
test/suite/connection/test.tls-versions.ts
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@@ -1,24 +1,20 @@
import { tap, expect } from '@git.zone/tstest/tapbundle';
import * as net from 'net';
import * as tls from 'tls';
import { startTestServer, stopTestServer } from '../../helpers/server.loader.js';
import type { SmtpServer } from '../../../ts/mail/delivery/smtpserver/index.js';
import { startTestServer, stopTestServer, type ITestServer } from '../../helpers/server.loader.js';
const TEST_PORT = 2525;
const TEST_PORT_TLS = 30465;
const TEST_TIMEOUT = 30000;
let testServer: SmtpServer;
let testServerTls: ITestServer;
let testServer: ITestServer;
tap.test('setup - start SMTP servers for TLS version tests', async () => {
testServer = await startTestServer();
await new Promise(resolve => setTimeout(resolve, 1000));testServerTls = await startTestServer();
tap.test('setup - start SMTP server with TLS support for version tests', async () => {
testServer = await startTestServer({
port: TEST_PORT,
tlsEnabled: true
});
await new Promise(resolve => setTimeout(resolve, 1000));
expect(testServerTls).toBeInstanceOf(Object);
expect(testServer).toBeDefined();
});
tap.test('TLS Versions - should support STARTTLS capability', async (tools) => {
@@ -89,18 +85,18 @@ tap.test('TLS Versions - should support STARTTLS capability', async (tools) => {
}
});
tap.test('TLS Versions - should support modern TLS versions on secure port', async (tools) => {
tap.test('TLS Versions - should support modern TLS versions via STARTTLS', async (tools) => {
const done = tools.defer();
try {
// Test TLS 1.2
console.log('Testing TLS 1.2 support...');
const tls12Result = await testTlsVersion('TLSv1.2', TEST_PORT_TLS);
// Test TLS 1.2 via STARTTLS
console.log('Testing TLS 1.2 support via STARTTLS...');
const tls12Result = await testTlsVersionViaStartTls('TLSv1.2', TEST_PORT);
console.log('TLS 1.2 result:', tls12Result);
// Test TLS 1.3
console.log('Testing TLS 1.3 support...');
const tls13Result = await testTlsVersion('TLSv1.3', TEST_PORT_TLS);
// Test TLS 1.3 via STARTTLS
console.log('Testing TLS 1.3 support via STARTTLS...');
const tls13Result = await testTlsVersionViaStartTls('TLSv1.3', TEST_PORT);
console.log('TLS 1.3 result:', tls13Result);
// At least one modern version should be supported
@@ -119,17 +115,17 @@ tap.test('TLS Versions - should support modern TLS versions on secure port', asy
}
});
tap.test('TLS Versions - should reject obsolete TLS versions', async (tools) => {
tap.test('TLS Versions - should reject obsolete TLS versions via STARTTLS', async (tools) => {
const done = tools.defer();
try {
// Test TLS 1.0 (should be rejected by modern servers)
console.log('Testing TLS 1.0 (obsolete)...');
const tls10Result = await testTlsVersion('TLSv1', TEST_PORT_TLS);
console.log('Testing TLS 1.0 (obsolete) via STARTTLS...');
const tls10Result = await testTlsVersionViaStartTls('TLSv1', TEST_PORT);
// Test TLS 1.1 (should be rejected by modern servers)
console.log('Testing TLS 1.1 (obsolete)...');
const tls11Result = await testTlsVersion('TLSv1.1', TEST_PORT_TLS);
console.log('Testing TLS 1.1 (obsolete) via STARTTLS...');
const tls11Result = await testTlsVersionViaStartTls('TLSv1.1', TEST_PORT);
// Modern servers should reject these old versions
// But some might still support them for compatibility
@@ -144,123 +140,221 @@ tap.test('TLS Versions - should reject obsolete TLS versions', async (tools) =>
}
});
tap.test('TLS Versions - should provide cipher information', async (tools) => {
tap.test('TLS Versions - should provide cipher information via STARTTLS', async (tools) => {
const done = tools.defer();
try {
const tlsOptions = {
// Connect to plain SMTP port
const socket = net.createConnection({
host: 'localhost',
port: TEST_PORT_TLS,
rejectUnauthorized: false,
port: TEST_PORT,
timeout: TEST_TIMEOUT
};
const socket = await new Promise<tls.TLSSocket>((resolve, reject) => {
const tlsSocket = tls.connect(tlsOptions, () => {
resolve(tlsSocket);
});
tlsSocket.on('error', reject);
setTimeout(() => reject(new Error('TLS connection timeout')), 5000);
});
// Get connection details
const cipher = socket.getCipher();
const protocol = socket.getProtocol();
const authorized = socket.authorized;
await new Promise<void>((resolve, reject) => {
socket.once('connect', () => resolve());
socket.once('error', reject);
});
console.log('TLS connection established:');
console.log('- Protocol:', protocol);
console.log('- Cipher:', cipher.name);
console.log('- Key exchange:', cipher.standardName);
console.log('- Authorized:', authorized);
expect(protocol).toBeDefined();
expect(cipher.name).toBeDefined();
// Send SMTP greeting to verify encrypted connection works
const banner = await new Promise<string>((resolve) => {
// Get banner
await new Promise<string>((resolve) => {
socket.once('data', (chunk) => resolve(chunk.toString()));
});
expect(banner).toInclude('220');
console.log('Received SMTP banner over TLS');
// Send EHLO
socket.write('EHLO testhost\r\n');
const ehloResponse = await new Promise<string>((resolve) => {
let data = '';
const handler = (chunk: Buffer) => {
data += chunk.toString();
if (data.includes('\r\n') && (data.match(/^250 /m) || data.match(/^250-.*\r\n250 /ms))) {
socket.removeListener('data', handler);
resolve(data);
}
};
socket.on('data', handler);
});
// Check for STARTTLS
if (!ehloResponse.includes('STARTTLS')) {
console.log('Server does not support STARTTLS - skipping cipher info test');
socket.write('QUIT\r\n');
socket.end();
done.resolve();
return;
}
// Send STARTTLS
socket.write('STARTTLS\r\n');
await new Promise<string>((resolve) => {
socket.once('data', (chunk) => resolve(chunk.toString()));
});
// Upgrade to TLS
const tlsSocket = tls.connect({
socket: socket,
servername: 'localhost',
rejectUnauthorized: false
});
await new Promise<void>((resolve, reject) => {
tlsSocket.once('secureConnect', () => resolve());
tlsSocket.once('error', reject);
});
// Get connection details
const cipher = tlsSocket.getCipher();
const protocol = tlsSocket.getProtocol();
const authorized = tlsSocket.authorized;
console.log('TLS connection established via STARTTLS:');
console.log('- Protocol:', protocol);
console.log('- Cipher:', cipher?.name);
console.log('- Key exchange:', cipher?.standardName);
console.log('- Authorized:', authorized);
if (protocol) {
expect(typeof protocol).toEqual('string');
}
if (cipher) {
expect(cipher.name).toBeDefined();
}
// Clean up
socket.write('QUIT\r\n');
socket.end();
tlsSocket.write('QUIT\r\n');
tlsSocket.end();
} finally {
done.resolve();
}
});
// Helper function to test specific TLS version
async function testTlsVersion(version: string, port: number): Promise<{success: boolean, cipher?: any, error?: string}> {
return new Promise((resolve) => {
const tlsOptions: any = {
host: 'localhost',
port: port,
rejectUnauthorized: false,
timeout: 5000
};
// Set version constraints based on requested version
switch (version) {
case 'TLSv1':
tlsOptions.minVersion = 'TLSv1';
tlsOptions.maxVersion = 'TLSv1';
break;
case 'TLSv1.1':
tlsOptions.minVersion = 'TLSv1.1';
tlsOptions.maxVersion = 'TLSv1.1';
break;
case 'TLSv1.2':
tlsOptions.minVersion = 'TLSv1.2';
tlsOptions.maxVersion = 'TLSv1.2';
break;
case 'TLSv1.3':
tlsOptions.minVersion = 'TLSv1.3';
tlsOptions.maxVersion = 'TLSv1.3';
break;
}
const socket = tls.connect(tlsOptions, () => {
const cipher = socket.getCipher();
const protocol = socket.getProtocol();
// Helper function to test specific TLS version via STARTTLS
async function testTlsVersionViaStartTls(version: string, port: number): Promise<{success: boolean, cipher?: any, error?: string}> {
return new Promise(async (resolve) => {
try {
// Connect to plain SMTP port
const socket = net.createConnection({
host: 'localhost',
port: port,
timeout: 5000
});
socket.destroy();
resolve({
success: true,
cipher: {
name: cipher.name,
standardName: cipher.standardName,
protocol: protocol
}
await new Promise<void>((socketResolve, socketReject) => {
socket.once('connect', () => socketResolve());
socket.once('error', socketReject);
});
});
socket.on('error', (error) => {
// Get banner
await new Promise<string>((bannerResolve) => {
socket.once('data', (chunk) => bannerResolve(chunk.toString()));
});
// Send EHLO
socket.write('EHLO testhost\r\n');
const ehloResponse = await new Promise<string>((ehloResolve) => {
let data = '';
const handler = (chunk: Buffer) => {
data += chunk.toString();
if (data.includes('\r\n') && (data.match(/^250 /m) || data.match(/^250-.*\r\n250 /ms))) {
socket.removeListener('data', handler);
ehloResolve(data);
}
};
socket.on('data', handler);
});
// Check for STARTTLS
if (!ehloResponse.includes('STARTTLS')) {
socket.destroy();
resolve({
success: false,
error: 'STARTTLS not supported'
});
return;
}
// Send STARTTLS
socket.write('STARTTLS\r\n');
await new Promise<string>((starttlsResolve) => {
socket.once('data', (chunk) => starttlsResolve(chunk.toString()));
});
// Set up TLS options with version constraints
const tlsOptions: any = {
socket: socket,
servername: 'localhost',
rejectUnauthorized: false
};
// Set version constraints based on requested version
switch (version) {
case 'TLSv1':
tlsOptions.minVersion = 'TLSv1';
tlsOptions.maxVersion = 'TLSv1';
break;
case 'TLSv1.1':
tlsOptions.minVersion = 'TLSv1.1';
tlsOptions.maxVersion = 'TLSv1.1';
break;
case 'TLSv1.2':
tlsOptions.minVersion = 'TLSv1.2';
tlsOptions.maxVersion = 'TLSv1.2';
break;
case 'TLSv1.3':
tlsOptions.minVersion = 'TLSv1.3';
tlsOptions.maxVersion = 'TLSv1.3';
break;
}
// Upgrade to TLS
const tlsSocket = tls.connect(tlsOptions);
tlsSocket.once('secureConnect', () => {
const cipher = tlsSocket.getCipher();
const protocol = tlsSocket.getProtocol();
tlsSocket.destroy();
resolve({
success: true,
cipher: {
name: cipher?.name,
standardName: cipher?.standardName,
protocol: protocol
}
});
});
tlsSocket.once('error', (error) => {
resolve({
success: false,
error: error.message
});
});
setTimeout(() => {
tlsSocket.destroy();
resolve({
success: false,
error: 'TLS handshake timeout'
});
}, 5000);
} catch (error) {
resolve({
success: false,
error: error.message
error: error instanceof Error ? error.message : 'Unknown error'
});
});
setTimeout(() => {
socket.destroy();
resolve({
success: false,
error: 'Connection timeout'
});
}, 5000);
}
});
}
tap.test('cleanup - stop SMTP servers', async () => {
await stopTestServer();
await stopTestServer(testServerTls);
tap.test('cleanup - stop SMTP server', async () => {
await stopTestServer(testServer);
expect(true).toEqual(true);
});