Fix email template loading and conditional TLS configuration

client/src/Pages/Settings/SettingsEmail.jsx

@@ -101,6 +101,47 @@ const SettingsEmail = ({
 		return null;
 	}
 
+	/**
+	 * Build email configuration object for code preview
+	 * Constructs the config incrementally instead of using nested conditional spreads
+	 */
+	const buildEmailConfigPreview = () => {
+		const config = {
+			host: systemEmailHost,
+			port: systemEmailPort,
+			secure: systemEmailSecure,
+			auth: {
+				user: systemEmailUser || systemEmailAddress,
+				pass: "<your_password>",
+			},
+			name: systemEmailConnectionHost || "localhost",
+			pool: systemEmailPool,
+		};
+
+		if (systemEmailSecure) {
+			if (systemEmailIgnoreTLS) {
+				config.ignoreTLS = systemEmailIgnoreTLS;
+			}
+			if (systemEmailRequireTLS) {
+				config.requireTLS = systemEmailRequireTLS;
+			}
+
+			const tlsSettings = {};
+			if (systemEmailRejectUnauthorized !== undefined) {
+				tlsSettings.rejectUnauthorized = systemEmailRejectUnauthorized;
+			}
+			if (systemEmailTLSServername && systemEmailTLSServername !== "") {
+				tlsSettings.servername = systemEmailTLSServername;
+			}
+
+			if (Object.keys(tlsSettings).length > 0) {
+				config.tls = tlsSettings;
+			}
+		}
+
+		return config;
+	};
+
 	return (
 		<ConfigBox>
 			<Box>
@@ -271,29 +312,7 @@ const SettingsEmail = ({
 								overflow: "auto",
 							}}
 						>
-							<code>
-								{JSON.stringify(
-									{
-										host: systemEmailHost,
-										port: systemEmailPort,
-										secure: systemEmailSecure,
-										auth: {
-											user: systemEmailUser || systemEmailAddress,
-											pass: "<your_password>",
-										},
-										name: systemEmailConnectionHost || "localhost",
-										pool: systemEmailPool,
-										tls: {
-											rejectUnauthorized: systemEmailRejectUnauthorized,
-											ignoreTLS: systemEmailIgnoreTLS,
-											requireTLS: systemEmailRequireTLS,
-											servername: systemEmailTLSServername,
-										},
-									},
-									null,
-									2
-								)}
-							</code>
+							<code>{JSON.stringify(buildEmailConfigPreview(), null, 2)}</code>
 						</Box>
 					</Box>
 

server/src/service/infrastructure/emailService.js

@@ -1,9 +1,3 @@
-import { fileURLToPath } from "url";
-import path from "path";
-
-const __filename = fileURLToPath(import.meta.url);
-const __dirname = path.dirname(__filename);
-
 const SERVICE_NAME = "EmailService";
 
 /**
@@ -46,16 +40,37 @@ class EmailService {
 		 */
 		this.loadTemplate = (templateName) => {
 			try {
-				const templatePath = this.path.join(__dirname, `../../../templates/${templateName}.mjml`);
+				// Use EMAIL_TEMPLATE_PATH environment variable or default to src/templates/ in cwd
+				const templateBase = process.env.EMAIL_TEMPLATE_PATH || this.path.join(process.cwd(), "src", "templates");
+				const templatePath = this.path.join(templateBase, `${templateName}.mjml`);
+
+				this.logger.debug({
+					message: `Loading template: ${templateName}`,
+					service: SERVICE_NAME,
+					method: "loadTemplate",
+					templatePath: templatePath,
+				});
+
 				const templateContent = this.fs.readFileSync(templatePath, "utf8");
-				return this.compile(templateContent);
+				const compiled = this.compile(templateContent);
+
+				this.logger.debug({
+					message: `Template loaded successfully: ${templateName}`,
+					service: SERVICE_NAME,
+					method: "loadTemplate",
+				});
+				return compiled;
 			} catch (error) {
 				this.logger.error({
-					message: error.message,
+					message: `Failed to load template '${templateName}': ${error.message}`,
 					service: SERVICE_NAME,
 					method: "loadTemplate",
+					templateName: templateName,
+					error: error.message,
 					stack: error.stack,
 				});
+				// Fail fast - throw error instead of returning empty function
+				throw error;
 			}
 		};
 
@@ -83,20 +98,169 @@ class EmailService {
 
 	buildEmail = async (template, context) => {
 		try {
+			if (!this.templateLookup[template]) {
+				this.logger.error({
+					message: `Template '${template}' not found in templateLookup`,
+					service: SERVICE_NAME,
+					method: "buildEmail",
+					availableTemplates: Object.keys(this.templateLookup),
+				});
+				throw new Error(`Template '${template}' not found`);
+			}
+			if (typeof this.templateLookup[template] !== "function") {
+				this.logger.error({
+					message: `Template '${template}' is not a function. Type: ${typeof this.templateLookup[template]}`,
+					service: SERVICE_NAME,
+					method: "buildEmail",
+					templateValue: this.templateLookup[template],
+				});
+				throw new Error(`Template '${template}' is not a function`);
+			}
 			const mjml = this.templateLookup[template](context);
+
+			// Check if MJML is empty (template failed to load)
+			if (!mjml || mjml.trim() === "") {
+				const msg = `Template '${template}' returned empty MJML content. Template may have failed to load.`;
+				this.logger.error({
+					message: msg,
+					service: SERVICE_NAME,
+					method: "buildEmail",
+					template: template,
+				});
+				throw new Error(msg);
+			}
+
 			const html = await this.mjml2html(mjml);
+
+			// Check if HTML is empty
+			if (!html || !html.html) {
+				const msg = `MJML conversion failed for template '${template}'. No HTML output.`;
+				this.logger.error({
+					message: msg,
+					service: SERVICE_NAME,
+					method: "buildEmail",
+					template: template,
+					mjmlLength: mjml.length,
+				});
+				throw new Error(msg);
+			}
+
 			return html.html;
 		} catch (error) {
 			this.logger.error({
-				message: error.message,
+				message: `Failed to build email for template '${template}': ${error.message}`,
 				service: SERVICE_NAME,
 				method: "buildEmail",
+				template: template,
+				error: error.message,
 				stack: error.stack,
 			});
+			throw error;
 		}
 	};
 
+	/**
+	 * Validates email parameters.
+	 * @param {string} to - The recipient email address.
+	 * @param {string} subject - The email subject.
+	 * @param {string} html - The email HTML content.
+	 * @returns {boolean} True if valid, false otherwise.
+	 */
+	validateEmailParams(to, subject, html) {
+		if (!to || !subject) {
+			this.logger.error({
+				message: "Invalid email parameters: missing 'to' or 'subject'",
+				service: SERVICE_NAME,
+				method: "validateEmailParams",
+			});
+			return false;
+		}
+
+		if (!html || html.trim() === "") {
+			this.logger.error({
+				message: "Cannot send email: HTML content is empty",
+				service: SERVICE_NAME,
+				method: "validateEmailParams",
+			});
+			return false;
+		}
+
+		return true;
+	}
+
+	/**
+	 * Validates the from email address.
+	 * @param {string} systemEmailAddress - The system email address.
+	 * @returns {boolean} True if valid, false otherwise.
+	 */
+	validateFromAddress(systemEmailAddress) {
+		const fromAddress = systemEmailAddress;
+		if (!fromAddress || !fromAddress.includes("@")) {
+			this.logger.error({
+				message: "Missing or invalid systemEmailAddress - a valid email address is required",
+				service: SERVICE_NAME,
+				method: "validateFromAddress",
+			});
+			return false;
+		}
+		return true;
+	}
+
+	/**
+	 * Builds the TLS configuration for the email transporter.
+	 * @param {Object} config - The email configuration object.
+	 * @returns {Object} The TLS configuration object.
+	 */
+	buildTLSConfig(config) {
+		const { systemEmailSecure, systemEmailIgnoreTLS, systemEmailRequireTLS, systemEmailRejectUnauthorized, systemEmailTLSServername } = config;
+
+		const tlsConfig = {};
+
+		// Only apply TLS settings if secure is enabled
+		if (systemEmailSecure) {
+			// Top-level Nodemailer options (control STARTTLS behavior):
+			// - ignoreTLS: If true, the connection will not attempt to use STARTTLS
+			// - requireTLS: If true, connection will fail if STARTTLS is not available
+			if (systemEmailIgnoreTLS !== undefined) {
+				tlsConfig.ignoreTLS = systemEmailIgnoreTLS;
+			}
+			if (systemEmailRequireTLS !== undefined) {
+				tlsConfig.requireTLS = systemEmailRequireTLS;
+			}
+
+			// Node.js TLS options (go inside the 'tls' object):
+			// - rejectUnauthorized: If false, accepts self-signed certificates
+			// - servername: Overrides the hostname for SNI (Server Name Indication)
+			const tlsSettings = {};
+
+			if (systemEmailRejectUnauthorized !== undefined) {
+				tlsSettings.rejectUnauthorized = systemEmailRejectUnauthorized;
+			}
+			if (systemEmailTLSServername !== undefined && systemEmailTLSServername !== null && systemEmailTLSServername !== "") {
+				tlsSettings.servername = systemEmailTLSServername;
+			}
+
+			// Only add tls property if we have TLS settings
+			if (Object.keys(tlsSettings).length > 0) {
+				tlsConfig.tls = tlsSettings;
+				this.logger.debug({
+					message: `TLS settings applied to email config`,
+					service: SERVICE_NAME,
+					method: "buildTLSConfig",
+					tlsSettings: Object.keys(tlsSettings),
+				});
+			}
+		}
+
+		return tlsConfig;
+	}
+
 	sendEmail = async (to, subject, html, transportConfig) => {
+		// Validate email parameters
+		if (!this.validateEmailParams(to, subject, html)) {
+			return false;
+		}
+
 		let config;
 		if (typeof transportConfig !== "undefined") {
 			config = transportConfig;
@@ -107,35 +271,35 @@ class EmailService {
 			systemEmailHost,
 			systemEmailPort,
 			systemEmailSecure,
-			systemEmailPool,
 			systemEmailUser,
 			systemEmailAddress,
 			systemEmailPassword,
 			systemEmailConnectionHost,
-			systemEmailTLSServername,
-			systemEmailIgnoreTLS,
-			systemEmailRequireTLS,
-			systemEmailRejectUnauthorized,
 		} = config;
 
+		// Validate from address
+		if (!this.validateFromAddress(systemEmailAddress)) {
+			return false;
+		}
+
+		// Build base email config
 		const emailConfig = {
 			host: systemEmailHost,
 			port: Number(systemEmailPort),
 			secure: systemEmailSecure,
+			pool: config.systemEmailPool ?? false,
 			auth: {
 				user: systemEmailUser || systemEmailAddress,
 				pass: systemEmailPassword,
 			},
 			name: systemEmailConnectionHost || "localhost",
 			connectionTimeout: 5000,
-			pool: systemEmailPool,
-			tls: {
-				rejectUnauthorized: systemEmailRejectUnauthorized,
-				ignoreTLS: systemEmailIgnoreTLS,
-				requireTLS: systemEmailRequireTLS,
-				servername: systemEmailTLSServername,
-			},
 		};
+
+		// Apply TLS configuration
+		const tlsConfig = this.buildTLSConfig(config);
+		Object.assign(emailConfig, tlsConfig);
+
 		this.transporter = this.nodemailer.createTransport(emailConfig);
 
 		try {
@@ -144,7 +308,8 @@ class EmailService {
 			this.logger.warn({
 				message: "Email transporter verification failed",
 				service: SERVICE_NAME,
-				method: "verifyTransporter",
+				method: "sendEmail",
+				error: error.message,
 			});
 			return false;
 		}
@@ -164,6 +329,7 @@ class EmailService {
 				method: "sendEmail",
 				stack: error.stack,
 			});
+			return false;
 		}
 	};
 }