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backend/node_modules/imapflow/test/proxy-connection-test.js

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+'use strict';
+
+const proxyquire = require('proxyquire').noCallThru();
+
+// Mock socket object
+const createMockSocket = () => ({
+    on: () => {},
+    write: () => {},
+    end: () => {},
+    destroy: () => {}
+});
+
+// Mock logger
+const createMockLogger = () => {
+    const logs = { info: [], error: [] };
+    return {
+        info: msg => logs.info.push(msg),
+        error: msg => logs.error.push(msg),
+        _logs: logs
+    };
+};
+
+// ============================================
+// HTTP Proxy Tests
+// ============================================
+
+module.exports['Proxy Connection: HTTP proxy success'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': (url, port, host, cb) => {
+            cb(null, mockSocket);
+        },
+        socks: { SocksClient: {} },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    const socket = await proxyConnection(logger, 'http://proxy.example.com:8080', '192.168.1.1', 993);
+
+    test.equal(socket, mockSocket);
+    test.equal(logger._logs.info.length, 1);
+    test.ok(logger._logs.info[0].msg.includes('HTTP proxy'));
+    test.done();
+};
+
+module.exports['Proxy Connection: HTTPS proxy success'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': (url, port, host, cb) => {
+            cb(null, mockSocket);
+        },
+        socks: { SocksClient: {} },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    const socket = await proxyConnection(logger, 'https://proxy.example.com:8080', '192.168.1.1', 993);
+
+    test.equal(socket, mockSocket);
+    test.equal(logger._logs.info.length, 1);
+    test.done();
+};
+
+module.exports['Proxy Connection: HTTP proxy with password hides it in logs'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': (url, port, host, cb) => {
+            cb(null, mockSocket);
+        },
+        socks: { SocksClient: {} },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    await proxyConnection(logger, 'http://user:secret123@proxy.example.com:8080', '192.168.1.1', 993);
+
+    test.equal(logger._logs.info.length, 1);
+    test.ok(!logger._logs.info[0].proxyUrl.includes('secret123'));
+    test.ok(logger._logs.info[0].proxyUrl.includes('(hidden)'));
+    test.done();
+};
+
+module.exports['Proxy Connection: HTTP proxy failure'] = async test => {
+    const logger = createMockLogger();
+    const testError = new Error('Connection refused');
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': (url, port, host, cb) => {
+            cb(testError);
+        },
+        socks: { SocksClient: {} },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    try {
+        await proxyConnection(logger, 'http://proxy.example.com:8080', '192.168.1.1', 993);
+        test.ok(false, 'Should have thrown');
+    } catch (err) {
+        test.equal(err, testError);
+        test.equal(logger._logs.error.length, 1);
+        test.ok(logger._logs.error[0].msg.includes('Failed'));
+    }
+
+    test.done();
+};
+
+module.exports['Proxy Connection: HTTP proxy failure hides password'] = async test => {
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': (url, port, host, cb) => {
+            cb(new Error('Failed'));
+        },
+        socks: { SocksClient: {} },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    try {
+        await proxyConnection(logger, 'http://user:secret@proxy.example.com:8080', '192.168.1.1', 993);
+    } catch (err) {
+        // Error expected - we just need to verify logging
+        err.expected = true;
+        test.ok(!logger._logs.error[0].proxyUrl.includes('secret'));
+        test.ok(logger._logs.error[0].proxyUrl.includes('(hidden)'));
+    }
+
+    test.done();
+};
+
+// ============================================
+// SOCKS Proxy Tests
+// ============================================
+
+module.exports['Proxy Connection: SOCKS5 proxy success'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async opts => {
+                    test.equal(opts.proxy.type, 5);
+                    test.equal(opts.command, 'connect');
+                    return { socket: mockSocket };
+                }
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    const socket = await proxyConnection(logger, 'socks5://proxy.example.com:1080', '192.168.1.1', 993);
+
+    test.equal(socket, mockSocket);
+    test.equal(logger._logs.info.length, 1);
+    test.ok(logger._logs.info[0].msg.includes('SOCKS proxy'));
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS proxy (defaults to SOCKS5)'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async opts => {
+                    test.equal(opts.proxy.type, 5); // Default to SOCKS5
+                    return { socket: mockSocket };
+                }
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    await proxyConnection(logger, 'socks://proxy.example.com:1080', '192.168.1.1', 993);
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS4 proxy'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async opts => {
+                    test.equal(opts.proxy.type, 4);
+                    return { socket: mockSocket };
+                }
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    await proxyConnection(logger, 'socks4://proxy.example.com:1080', '192.168.1.1', 993);
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS4a proxy'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async opts => {
+                    test.equal(opts.proxy.type, 4);
+                    return { socket: mockSocket };
+                }
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    await proxyConnection(logger, 'socks4a://proxy.example.com:1080', '192.168.1.1', 993);
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS proxy with authentication'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async opts => {
+                    test.equal(opts.proxy.userId, 'testuser');
+                    test.equal(opts.proxy.password, 'testpass');
+                    return { socket: mockSocket };
+                }
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    await proxyConnection(logger, 'socks5://testuser:testpass@proxy.example.com:1080', '192.168.1.1', 993);
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS proxy hides password in logs'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async () => ({ socket: mockSocket })
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    await proxyConnection(logger, 'socks5://user:secretpass@proxy.example.com:1080', '192.168.1.1', 993);
+
+    test.ok(!logger._logs.info[0].proxyUrl.includes('secretpass'));
+    test.ok(logger._logs.info[0].proxyUrl.includes('(hidden)'));
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS proxy default port'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async opts => {
+                    test.equal(opts.proxy.port, 1080); // Default SOCKS port
+                    return { socket: mockSocket };
+                }
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    await proxyConnection(logger, 'socks5://proxy.example.com', '192.168.1.1', 993);
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS proxy failure'] = async test => {
+    const logger = createMockLogger();
+    const testError = new Error('SOCKS connection failed');
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async () => {
+                    throw testError;
+                }
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    try {
+        await proxyConnection(logger, 'socks5://proxy.example.com:1080', '192.168.1.1', 993);
+        test.ok(false, 'Should have thrown');
+    } catch (err) {
+        test.equal(err, testError);
+        test.equal(logger._logs.error.length, 1);
+        test.ok(logger._logs.error[0].msg.includes('Failed'));
+    }
+
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS proxy failure hides password'] = async test => {
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async () => {
+                    throw new Error('Failed');
+                }
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    try {
+        await proxyConnection(logger, 'socks5://user:secret@proxy.example.com:1080', '192.168.1.1', 993);
+    } catch (err) {
+        // Error expected - we just need to verify logging
+        err.expected = true;
+        test.ok(!logger._logs.error[0].proxyUrl.includes('secret'));
+        test.ok(logger._logs.error[0].proxyUrl.includes('(hidden)'));
+    }
+
+    test.done();
+};
+
+// ============================================
+// DNS Resolution Tests
+// ============================================
+
+module.exports['Proxy Connection: Resolves hostname to IP'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+    let resolvedHost = null;
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': (url, port, host, cb) => {
+            resolvedHost = host;
+            cb(null, mockSocket);
+        },
+        socks: { SocksClient: {} },
+        dns: {
+            promises: {
+                resolve: async hostname => {
+                    if (hostname === 'mail.example.com') {
+                        return ['93.184.216.34'];
+                    }
+                    return [];
+                }
+            }
+        },
+        net: { isIP: host => /^\d+\.\d+\.\d+\.\d+$/.test(host) }
+    });
+
+    await proxyConnection(logger, 'http://proxy.example.com:8080', 'mail.example.com', 993);
+
+    test.equal(resolvedHost, '93.184.216.34');
+    test.done();
+};
+
+module.exports['Proxy Connection: Skips DNS for IP addresses'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+    let dnsResolveCalled = false;
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': (url, port, host, cb) => {
+            cb(null, mockSocket);
+        },
+        socks: { SocksClient: {} },
+        dns: {
+            promises: {
+                resolve: async () => {
+                    dnsResolveCalled = true;
+                    return ['127.0.0.1'];
+                }
+            }
+        },
+        net: { isIP: () => true } // Pretend it's already an IP
+    });
+
+    await proxyConnection(logger, 'http://proxy.example.com:8080', '192.168.1.1', 993);
+
+    test.equal(dnsResolveCalled, false);
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS resolves proxy hostname'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+    let proxyHostResolved = null;
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async opts => {
+                    proxyHostResolved = opts.proxy.host;
+                    return { socket: mockSocket };
+                }
+            }
+        },
+        dns: {
+            promises: {
+                resolve: async hostname => {
+                    if (hostname === 'proxy.example.com') {
+                        return ['10.0.0.1'];
+                    }
+                    return ['127.0.0.1'];
+                }
+            }
+        },
+        net: { isIP: host => /^\d+\.\d+\.\d+\.\d+$/.test(host) }
+    });
+
+    await proxyConnection(logger, 'socks5://proxy.example.com:1080', '192.168.1.1', 993);
+
+    test.equal(proxyHostResolved, '10.0.0.1');
+    test.done();
+};
+
+// ============================================
+// Edge Cases
+// ============================================
+
+module.exports['Proxy Connection: Unknown protocol returns undefined'] = async test => {
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: { SocksClient: {} },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    const result = await proxyConnection(logger, 'ftp://proxy.example.com:21', '192.168.1.1', 993);
+
+    test.equal(result, undefined);
+    test.done();
+};
+
+module.exports['Proxy Connection: HTTP proxy with no socket returned'] = async test => {
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': (url, port, host, cb) => {
+            cb(null, null); // No socket
+        },
+        socks: { SocksClient: {} },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    const socket = await proxyConnection(logger, 'http://proxy.example.com:8080', '192.168.1.1', 993);
+
+    test.equal(socket, null);
+    // No log when socket is null
+    test.equal(logger._logs.info.length, 0);
+    test.done();
+};
+
+module.exports['Proxy Connection: DNS returns empty result'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+    let usedHost = null;
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': (url, port, host, cb) => {
+            usedHost = host;
+            cb(null, mockSocket);
+        },
+        socks: { SocksClient: {} },
+        dns: {
+            promises: {
+                resolve: async () => [] // Empty result
+            }
+        },
+        net: { isIP: () => false }
+    });
+
+    await proxyConnection(logger, 'http://proxy.example.com:8080', 'mail.example.com', 993);
+
+    // Should keep original hostname when DNS returns empty
+    test.equal(usedHost, 'mail.example.com');
+    test.done();
+};
+
+module.exports['Proxy Connection: SOCKS with username only'] = async test => {
+    const mockSocket = createMockSocket();
+    const logger = createMockLogger();
+
+    const { proxyConnection } = proxyquire('../lib/proxy-connection', {
+        'nodemailer/lib/smtp-connection/http-proxy-client': () => {},
+        socks: {
+            SocksClient: {
+                createConnection: async opts => {
+                    test.equal(opts.proxy.userId, 'testuser');
+                    test.equal(opts.proxy.password, ''); // Empty string from URL parsing
+                    return { socket: mockSocket };
+                }
+            }
+        },
+        dns: { promises: { resolve: async () => ['127.0.0.1'] } },
+        net: { isIP: () => true }
+    });
+
+    await proxyConnection(logger, 'socks5://testuser@proxy.example.com:1080', '192.168.1.1', 993);
+    test.done();
+};