mailer/ts/mail/delivery/smtpserver/certificate-utils.ts

/**
 * Certificate Utilities for SMTP Server
 * Provides utilities for managing TLS certificates
 */

import * as fs from 'fs';
import * as tls from 'tls';
import { SmtpLogger } from './utils/logging.ts';

/**
 * Certificate data
 */
export interface ICertificateData {
  key: Buffer;
  cert: Buffer;
  ca?: Buffer;
}

/**
 * Normalize a PEM certificate string
 * @param str - Certificate string
 * @returns Normalized certificate string
 */
function normalizeCertificate(str: string | Buffer): string {
  // Handle different input types
  let inputStr: string;
  
  if (Buffer.isBuffer(str)) {
    // Convert Buffer to string using utf8 encoding
    inputStr = str.toString('utf8');
  } else if (typeof str === 'string') {
    inputStr = str;
  } else {
    throw new Error('Certificate must be a string or Buffer');
  }
  
  if (!inputStr) {
    throw new Error('Empty certificate data');
  }

  // Remove any whitespace around the string
  let normalizedStr = inputStr.trim();
  
  // Make sure it has proper PEM format
  if (!normalizedStr.includes('-----BEGIN ')) {
    throw new Error('Invalid certificate format: Missing BEGIN marker');
  }
  
  if (!normalizedStr.includes('-----END ')) {
    throw new Error('Invalid certificate format: Missing END marker');
  }
  
  // Normalize line endings (replace Windows-style \r\n with Unix-style \n)
  normalizedStr = normalizedStr.replace(/\r\n/g, '\n');
  
  // Only normalize if the certificate appears to have formatting issues
  // Check if the certificate is already properly formatted
  const lines = normalizedStr.split('\n');
  let needsReformatting = false;
  
  // Check for common formatting issues:
  // 1. Missing line breaks after header/before footer
  // 2. Lines that are too long or too short (except header/footer)
  // 3. Multiple consecutive blank lines
  for (let i = 0; i < lines.length; i++) {
    const line = lines[i].trim();
    if (line.startsWith('-----BEGIN ') || line.startsWith('-----END ')) {
      continue; // Skip header/footer lines
    }
    if (line.length === 0) {
      continue; // Skip empty lines
    }
    // Check if content lines are reasonable length (base64 is typically 64 chars per line)
    if (line.length > 76) { // Allow some flexibility beyond standard 64
      needsReformatting = true;
      break;
    }
  }
  
  // Only reformat if necessary
  if (needsReformatting) {
    const beginMatch = normalizedStr.match(/^(-----BEGIN [^-]+-----)(.*)$/s);
    const endMatch = normalizedStr.match(/(.*)(-----END [^-]+-----)$/s);
    
    if (beginMatch && endMatch) {
      const header = beginMatch[1];
      const footer = endMatch[2];
      let content = normalizedStr.substring(header.length, normalizedStr.length - footer.length);
      
      // Clean up only line breaks and carriage returns, preserve base64 content
      content = content.replace(/[\n\r]/g, '').trim();
      
      // Add proper line breaks (every 64 characters)
      let formattedContent = '';
      for (let i = 0; i < content.length; i += 64) {
        formattedContent += content.substring(i, Math.min(i + 64, content.length)) + '\n';
      }
      
      // Reconstruct the certificate
      return header + '\n' + formattedContent + footer;
    }
  }
  
  return normalizedStr;
}

/**
 * Load certificates from PEM format strings
 * @param options - Certificate options
 * @returns Certificate data with Buffer format
 */
export function loadCertificatesFromString(options: {
  key: string | Buffer;
  cert: string | Buffer;
  ca?: string | Buffer;
}): ICertificateData {
  try {
    // First try to use certificates without normalization
    try {
      let keyStr: string;
      let certStr: string;
      let caStr: string | undefined;
      
      // Convert inputs to strings without aggressive normalization
      if (Buffer.isBuffer(options.key)) {
        keyStr = options.key.toString('utf8');
      } else {
        keyStr = options.key;
      }
      
      if (Buffer.isBuffer(options.cert)) {
        certStr = options.cert.toString('utf8');
      } else {
        certStr = options.cert;
      }
      
      if (options.ca) {
        if (Buffer.isBuffer(options.ca)) {
          caStr = options.ca.toString('utf8');
        } else {
          caStr = options.ca;
        }
      }
      
      // Simple cleanup - only normalize line endings
      keyStr = keyStr.trim().replace(/\r\n/g, '\n');
      certStr = certStr.trim().replace(/\r\n/g, '\n');
      if (caStr) {
        caStr = caStr.trim().replace(/\r\n/g, '\n');
      }
      
      // Convert to buffers
      const keyBuffer = Buffer.from(keyStr, 'utf8');
      const certBuffer = Buffer.from(certStr, 'utf8');
      const caBuffer = caStr ? Buffer.from(caStr, 'utf8') : undefined;
      
      // Test the certificates first
      const secureContext = tls.createSecureContext({
        key: keyBuffer,
        cert: certBuffer,
        ca: caBuffer
      });
      
      SmtpLogger.info('Successfully validated certificates without normalization');
      
      return {
        key: keyBuffer,
        cert: certBuffer,
        ca: caBuffer
      };
      
    } catch (simpleError) {
      SmtpLogger.warn(`Simple certificate loading failed, trying normalization: ${simpleError instanceof Error ? simpleError.message : String(simpleError)}`);
      
      // DEBUG: Log certificate details when simple loading fails
      SmtpLogger.warn('Certificate loading failure details', {
        keyType: typeof options.key,
        certType: typeof options.cert,
        keyIsBuffer: Buffer.isBuffer(options.key),
        certIsBuffer: Buffer.isBuffer(options.cert),
        keyLength: options.key ? options.key.length : 0,
        certLength: options.cert ? options.cert.length : 0,
        keyPreview: options.key ? (typeof options.key === 'string' ? options.key.substring(0, 50) : options.key.toString('utf8').substring(0, 50)) : 'null',
        certPreview: options.cert ? (typeof options.cert === 'string' ? options.cert.substring(0, 50) : options.cert.toString('utf8').substring(0, 50)) : 'null'
      });
    }
    
    // Fallback: Try to fix and normalize certificates
    try {
      // Normalize certificates (handles both string and Buffer inputs)
      const key = normalizeCertificate(options.key);
      const cert = normalizeCertificate(options.cert);
      const ca = options.ca ? normalizeCertificate(options.ca) : undefined;
      
      // Convert normalized strings to Buffer with explicit utf8 encoding
      const keyBuffer = Buffer.from(key, 'utf8');
      const certBuffer = Buffer.from(cert, 'utf8');
      const caBuffer = ca ? Buffer.from(ca, 'utf8') : undefined;
      
      // Log for debugging
      SmtpLogger.debug('Certificate properties', {
        keyLength: keyBuffer.length,
        certLength: certBuffer.length,
        caLength: caBuffer ? caBuffer.length : 0
      });
      
      // Validate the certificates by attempting to create a secure context
      try {
        const secureContext = tls.createSecureContext({
          key: keyBuffer,
          cert: certBuffer,
          ca: caBuffer
        });
        
        // If createSecureContext doesn't throw, the certificates are valid
        SmtpLogger.info('Successfully validated certificate format');
      } catch (validationError) {
        // Log detailed error information for debugging
        SmtpLogger.error(`Certificate validation error: ${validationError instanceof Error ? validationError.message : String(validationError)}`);
        SmtpLogger.debug('Certificate validation details', {
          keyPreview: keyBuffer.toString('utf8').substring(0, 100) + '...',
          certPreview: certBuffer.toString('utf8').substring(0, 100) + '...',
          keyLength: keyBuffer.length,
          certLength: certBuffer.length
        });
        throw validationError;
      }
      
      return {
        key: keyBuffer,
        cert: certBuffer,
        ca: caBuffer
      };
    } catch (innerError) {
      SmtpLogger.warn(`Certificate normalization failed: ${innerError instanceof Error ? innerError.message : String(innerError)}`);
      throw innerError;
    }
  } catch (error) {
    SmtpLogger.error(`Error loading certificates: ${error instanceof Error ? error.message : String(error)}`);
    throw error;
  }
}

/**
 * Load certificates from files
 * @param options - Certificate file paths
 * @returns Certificate data with Buffer format
 */
export function loadCertificatesFromFiles(options: {
  keyPath: string;
  certPath: string;
  caPath?: string;
}): ICertificateData {
  try {
    // Read files directly as Buffers
    const key = fs.readFileSync(options.keyPath);
    const cert = fs.readFileSync(options.certPath);
    const ca = options.caPath ? fs.readFileSync(options.caPath) : undefined;
    
    // Log for debugging
    SmtpLogger.debug('Certificate file properties', {
      keyLength: key.length,
      certLength: cert.length,
      caLength: ca ? ca.length : 0
    });
    
    // Validate the certificates by attempting to create a secure context
    try {
      const secureContext = tls.createSecureContext({
        key,
        cert,
        ca
      });
      
      // If createSecureContext doesn't throw, the certificates are valid
      SmtpLogger.info('Successfully validated certificate files');
    } catch (validationError) {
      SmtpLogger.error(`Certificate file validation error: ${validationError instanceof Error ? validationError.message : String(validationError)}`);
      throw validationError;
    }
    
    return {
      key,
      cert,
      ca
    };
  } catch (error) {
    SmtpLogger.error(`Error loading certificate files: ${error instanceof Error ? error.message : String(error)}`);
    throw error;
  }
}

/**
 * Generate self-signed certificates for testing
 * @returns Certificate data with Buffer format
 */
export function generateSelfSignedCertificates(): ICertificateData {
  // This is for fallback/testing only - log a warning
  SmtpLogger.warn('Generating self-signed certificates for testing - DO NOT USE IN PRODUCTION');
  
  // Create selfsigned certificates using node-forge or similar library
  // For now, use hardcoded certificates as a last resort
  const key = Buffer.from(`-----BEGIN PRIVATE KEY-----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-----END PRIVATE KEY-----`, 'utf8');

  const cert = Buffer.from(`-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----`, 'utf8');
  
  return {
    key,
    cert
  };
}

/**
 * Create TLS options for secure server or STARTTLS
 * @param certificates - Certificate data
 * @param isServer - Whether this is for server (true) or client (false)
 * @returns TLS options
 */
export function createTlsOptions(
  certificates: ICertificateData,
  isServer: boolean = true
): tls.TlsOptions {
  const options: tls.TlsOptions = {
    key: certificates.key,
    cert: certificates.cert,
    ca: certificates.ca,
    // Support a wider range of TLS versions for better compatibility
    minVersion: 'TLSv1',  // Support older TLS versions (minimum TLS 1.0)
    maxVersion: 'TLSv1.3', // Support latest TLS version (1.3)
    // Cipher suites for broad compatibility
    ciphers: 'HIGH:MEDIUM:!aNULL:!eNULL:!NULL:!ADH:!RC4',
    // For testing, allow unauthorized (self-signed certs)
    rejectUnauthorized: false,
    // Longer handshake timeout for reliability
    handshakeTimeout: 30000,
    // TLS renegotiation option (removed - not supported in newer Node.ts)
    // Increase timeout for better reliability under test conditions
    sessionTimeout: 600,
    // Let the client choose the cipher for better compatibility
    honorCipherOrder: false,
    // For debugging
    enableTrace: true,
    // Disable secure options to allow more flexibility
    secureOptions: 0
  };
  
  // Server-specific options
  if (isServer) {
    options.ALPNProtocols = ['smtp']; // Accept non-ALPN connections (legacy clients)
  }
  
  return options;
}