tractatus/src/services/email.service.js

const nodemailer = require('nodemailer');
const Handlebars = require('handlebars');
const { convert: htmlToText } = require('html-to-text');
const fs = require('fs').promises;
const path = require('path');
const logger = require('../utils/logger.util');

/**
 * Smart port detection for ProtonBridge
 * Production uses port 1026, development uses 1025
 */
const getSmtpPort = () => {
  // Respect SMTP_PORT from .env (highest priority)
  if (process.env.SMTP_PORT) {
    const port = parseInt(process.env.SMTP_PORT);
    logger.info(`[EmailService] Using SMTP_PORT from .env: ${port}`);
    return port;
  }

  // Allow manual override (fallback)
  if (process.env.SMTP_PORT_OVERRIDE) {
    return parseInt(process.env.SMTP_PORT_OVERRIDE);
  }

  // Default fallback
  return 587;
};

class EmailService {
  constructor() {
    this.templatesPath = path.join(__dirname, '../../email-templates');
    this.templateCache = new Map();
    this.transporter = null;
    this.isInitialized = false;

    // Initialize email service
    this.initialize();
  }

  /**
   * Initialize Nodemailer transporter with ProtonBridge
   */
  initialize() {
    // Check if email is enabled
    if (process.env.EMAIL_ENABLED !== 'true') {
      logger.info('[EmailService] Email service disabled (EMAIL_ENABLED != true)');
      this.isInitialized = false;
      return;
    }

    if (!process.env.SMTP_HOST || !process.env.SMTP_USER || !process.env.SMTP_PASS) {
      logger.warn('[EmailService] Email configuration incomplete - email sending disabled');
      logger.warn('[EmailService] Required: SMTP_HOST, SMTP_USER, SMTP_PASS');
      this.isInitialized = false;
      return;
    }

    const smtpPort = getSmtpPort();

    try {
      // Create Nodemailer transporter
      this.transporter = nodemailer.createTransport({
        host: process.env.SMTP_HOST,        // 127.0.0.1 for ProtonBridge
        port: smtpPort,                      // 1026 (prod) or 1025 (dev)
        secure: process.env.SMTP_SECURE === 'true',  // false for localhost
        auth: {
          user: process.env.SMTP_USER,
          pass: process.env.SMTP_PASS
        },
        tls: {
          rejectUnauthorized: false,  // localhost is secure
          minVersion: 'TLSv1.2',
        },
        pool: true,                    // Use connection pooling
        maxConnections: 5,             // Max concurrent connections
        maxMessages: 100,              // Max messages per connection
        rateLimit: 10                  // 10 messages per second max
      });

      this.isInitialized = true;
      logger.info('[EmailService] Email service initialized successfully', {
        host: process.env.SMTP_HOST,
        port: smtpPort,
        user: process.env.SMTP_USER,
        provider: process.env.EMAIL_PROVIDER || 'smtp'
      });

      // Verify SMTP connection
      this.verifyConnection();

    } catch (error) {
      logger.error('[EmailService] Failed to initialize email service:', error);
      this.isInitialized = false;
    }
  }

  /**
   * Verify SMTP connection (async, doesn't block initialization)
   */
  async verifyConnection() {
    try {
      await this.transporter.verify();
      logger.info('[EmailService] SMTP connection verified successfully');
    } catch (error) {
      logger.error('[EmailService] SMTP connection verification failed:', error);
      logger.error('[EmailService] Please check ProtonBridge is running and credentials are correct');
    }
  }

  /**
   * Check if email service is available
   */
  async checkConnection() {
    if (!this.isInitialized || !this.transporter) {
      return false;
    }

    try {
      await this.transporter.verify();
      return true;
    } catch (error) {
      return false;
    }
  }

  /**
   * Load and compile template
   */
  async loadTemplate(templateName) {
    if (this.templateCache.has(templateName)) {
      return this.templateCache.get(templateName);
    }

    const templatePath = path.join(this.templatesPath, `${templateName}.html`);
    const templateContent = await fs.readFile(templatePath, 'utf8');
    const compiled = Handlebars.compile(templateContent);

    this.templateCache.set(templateName, compiled);
    return compiled;
  }

  /**
   * Render email from templates
   */
  async renderEmail(tier, variables) {
    try {
      // Load base template
      const baseTemplate = await this.loadTemplate('base-template');

      // Load content module for tier
      const contentTemplates = {
        'research': 'research-updates-content',
        'implementation': 'implementation-notes-content',
        'governance': 'governance-discussions-content',
        'project-updates': 'project-updates-content'
      };

      const contentTemplateName = contentTemplates[tier];
      if (!contentTemplateName) {
        throw new Error(`Unknown newsletter tier: ${tier}`);
      }

      const contentTemplate = await this.loadTemplate(contentTemplateName);

      // Render content module
      const renderedContent = contentTemplate(variables);

      // Render final email
      const finalHtml = baseTemplate({
        ...variables,
        content_body: renderedContent
      });

      // Generate plain text
      const plainText = htmlToText(finalHtml, {
        wordwrap: 80,
        ignoreImages: true,
        preserveNewlines: true
      });

      return { html: finalHtml, text: plainText };
    } catch (error) {
      logger.error('[EmailService] Template rendering error:', error);
      throw error;
    }
  }

  /**
   * Send email via SMTP (ProtonBridge or other)
   */
  async send({ to, subject, html, text, from = null }) {
    if (!this.isInitialized || !this.transporter) {
      logger.warn('[EmailService] Email sending skipped - service not initialized');
      return { success: false, error: 'Email service not configured' };
    }

    const fromAddress = from ||
      process.env.EMAIL_FROM ||
      process.env.SMTP_USER ||
      'noreply@agenticgovernance.digital';

    try {
      const info = await this.transporter.sendMail({
        from: fromAddress,
        to,
        subject,
        html,
        text
      });

      logger.info('[EmailService] Email sent successfully', {
        to,
        subject,
        messageId: info.messageId
      });

      return { success: true, messageId: info.messageId };
    } catch (error) {
      logger.error('[EmailService] Send error:', error);
      return { success: false, error: error.message };
    }
  }

  /**
   * Send newsletter to subscribers
   */
  async sendNewsletter({ tier, subject, previewText, variables, testMode = false, testEmail = null }) {
    const NewsletterSubscription = require('../models/NewsletterSubscription.model');

    try {
      // Get subscribers for tier
      let subscribers;
      if (testMode) {
        subscribers = [{ email: testEmail, name: 'Test User', verification_token: 'test-token' }];
      } else {
        subscribers = await NewsletterSubscription.findByInterest(tier, { verified: true, active: true });
      }

      if (subscribers.length === 0) {
        return {
          success: true,
          message: 'No subscribers found for tier',
          sent: 0,
          failed: 0
        };
      }

      // Render base templates
      const results = {
        sent: 0,
        failed: 0,
        errors: []
      };

      // Send to each subscriber
      for (const subscriber of subscribers) {
        try {
          // Generate unsubscribe/preferences links
          const unsubscribeLink = `${process.env.NEWSLETTER_UNSUBSCRIBE_BASE_URL}?token=${subscriber.verification_token}`;
          const preferencesLink = `${process.env.NEWSLETTER_PREFERENCES_BASE_URL}?token=${subscriber.verification_token}`;

          // Render email with subscriber-specific data
          const { html, text } = await this.renderEmail(tier, {
            name: subscriber.name || 'there',
            tier_name: this.getTierDisplayName(tier),
            unsubscribe_link: unsubscribeLink,
            preferences_link: preferencesLink,
            ...variables
          });

          // Send
          const result = await this.send({
            to: subscriber.email,
            subject,
            html,
            text
          });

          if (result.success) {
            results.sent++;
          } else {
            results.failed++;
            results.errors.push({ email: subscriber.email, error: result.error });
          }

        } catch (error) {
          results.failed++;
          results.errors.push({ email: subscriber.email, error: error.message });
          logger.error('[EmailService] Failed to send to subscriber:', { email: subscriber.email, error });
        }
      }

      return {
        success: true,
        message: `Newsletter sent: ${results.sent} successful, ${results.failed} failed`,
        sent: results.sent,
        failed: results.failed,
        errors: results.errors.length > 0 ? results.errors : undefined
      };

    } catch (error) {
      logger.error('[EmailService] Newsletter send error:', error);
      throw error;
    }
  }

  getTierDisplayName(tier) {
    const names = {
      'research': 'Research Updates',
      'implementation': 'Implementation Notes',
      'governance': 'Governance Discussions',
      'project-updates': 'Project Updates'
    };
    return names[tier] || tier;
  }
}

module.exports = new EmailService();