diff --git a/client/src/Pages/Settings/SettingsEmail.jsx b/client/src/Pages/Settings/SettingsEmail.jsx
index 88f8f98c1..e7ae88154 100644
--- a/client/src/Pages/Settings/SettingsEmail.jsx
+++ b/client/src/Pages/Settings/SettingsEmail.jsx
@@ -12,6 +12,7 @@ import { useTranslation } from "react-i18next";
 import { PasswordEndAdornment } from "../../Components/Inputs/TextInput/Adornments";
 import { useSendTestEmail } from "../../Hooks/useSendTestEmail";
 import { createToast } from "../../Utils/toastUtils";
+import { Switch } from "@mui/material";
 
 const SettingsEmail = ({
 	isAdmin,
@@ -25,6 +26,21 @@ const SettingsEmail = ({
 	const { t } = useTranslation();
 	const theme = useTheme();
 
+	// Destructure settings with default values
+	const {
+		systemEmailHost = "",
+		systemEmailPort = "",
+		systemEmailSecure = false,
+		systemEmailPool = false,
+		systemEmailUser = "",
+		systemEmailAddress = "",
+		systemEmailPassword = "",
+		systemEmailTLSServername = "",
+		systemEmailConnectionHost = "localhost",
+		systemEmailIgnoreTLS = false,
+		systemEmailRequireTLS = false,
+		systemEmailRejectUnauthorized = true,
+	} = settingsData?.settings || {};
 	// Local state
 	const [password, setPassword] = useState("");
 	const [hasBeenReset, setHasBeenReset] = useState(false);
@@ -47,18 +63,32 @@ const SettingsEmail = ({
 	const handleSendTestEmail = () => {
 		// Collect current form values
 		const emailConfig = {
-			systemEmailHost: settingsData?.settings?.systemEmailHost,
-			systemEmailPort: settingsData?.settings?.systemEmailPort,
-			systemEmailUser: settingsData?.settings?.systemEmailUser,
-			systemEmailAddress: settingsData?.settings?.systemEmailAddress,
-			systemEmailPassword: password || settingsData?.settings?.systemEmailPassword,
-			systemEmailConnectionHost: settingsData?.settings?.systemEmailConnectionHost,
+			systemEmailHost,
+			systemEmailPort,
+			systemEmailSecure,
+			systemEmailPool,
+			systemEmailUser,
+			systemEmailAddress,
+			systemEmailPassword: password || systemEmailPassword,
+			systemEmailTLSServername,
+			systemEmailConnectionHost,
+			systemEmailIgnoreTLS,
+			systemEmailRequireTLS,
+			systemEmailRejectUnauthorized,
 		};
 
 		// Basic validation
-		if (!emailConfig.systemEmailHost || !emailConfig.systemEmailPort) {
+		if (
+			!emailConfig.systemEmailHost ||
+			!emailConfig.systemEmailPort ||
+			!emailConfig.systemEmailAddress ||
+			!emailConfig.systemEmailPassword
+		) {
 			createToast({
-				body: t("settingsEmailRequiredFields", "Email host and port are required"),
+				body: t(
+					"settingsEmailRequiredFields",
+					"Email address, host, port and password are required"
+				),
 				variant: "error",
 			});
 			return;
@@ -90,7 +120,7 @@ const SettingsEmail = ({
 						<TextInput
 							name="systemEmailHost"
 							placeholder="smtp.gmail.com"
-							value={settingsData?.settings?.systemEmailHost ?? ""}
+							value={systemEmailHost}
 							onChange={handleChange}
 						/>
 					</Box>
@@ -100,7 +130,7 @@ const SettingsEmail = ({
 							name="systemEmailPort"
 							placeholder="425"
 							type="number"
-							value={settingsData?.settings?.systemEmailPort ?? ""}
+							value={systemEmailPort}
 							onChange={handleChange}
 						/>
 					</Box>
@@ -109,7 +139,7 @@ const SettingsEmail = ({
 						<TextInput
 							name="systemEmailUser"
 							placeholder="Leave empty if not required"
-							value={settingsData?.settings?.systemEmailUser ?? ""}
+							value={systemEmailUser}
 							onChange={handleChange}
 						/>
 					</Box>
@@ -118,7 +148,7 @@ const SettingsEmail = ({
 						<TextInput
 							name="systemEmailAddress"
 							placeholder="uptime@bluewavelabs.ca"
-							value={settingsData?.settings?.systemEmailAddress ?? ""}
+							value={systemEmailAddress}
 							onChange={handleChange}
 						/>
 					</Box>
@@ -156,23 +186,75 @@ const SettingsEmail = ({
 						</Box>
 					)}
 					<Box>
-						<Typography>{t("settingsEmailConnectionHost")}</Typography>
+						<Typography>{t("settingsEmailTLSServername")}</Typography>
 						<TextInput
-							name="systemEmailConnectionHost"
+							name="systemEmailTLSServername"
 							placeholder="bluewavelabs.ca"
-							value={settingsData?.settings?.systemEmailConnectionHost ?? ""}
+							value={systemEmailTLSServername}
 							onChange={handleChange}
 						/>
 					</Box>
 					<Box>
-						<Button
-							variant="contained"
-							color="accent"
-							loading={isSending}
-							onClick={handleSendTestEmail}
-						>
-							{t("settingsTestEmail", "Send test e-mail")}
-						</Button>
+						<Typography>{t("settingsEmailConnectionHost")}</Typography>
+						<TextInput
+							name="systemEmailConnectionHost"
+							placeholder="bluewavelabs.ca"
+							value={systemEmailConnectionHost}
+							onChange={handleChange}
+						/>
+					</Box>
+					<Box
+						sx={{
+							display: "flex",
+							flexDirection: "column",
+							gap: theme.spacing(4),
+						}}
+					>
+						<Typography>{t("settingsEmailSecure")}</Typography>
+						<Switch
+							name="systemEmailSecure"
+							checked={systemEmailSecure}
+							onChange={handleChange}
+						/>
+						<Typography>{t("settingsEmailPool")}</Typography>
+						<Switch
+							name="systemEmailPool"
+							checked={systemEmailPool}
+							onChange={handleChange}
+						/>
+						<Typography>{t("settingsEmailIgnoreTLS")}</Typography>
+						<Switch
+							name="systemEmailIgnoreTLS"
+							checked={systemEmailIgnoreTLS}
+							onChange={handleChange}
+						/>
+						<Typography>{t("settingsEmailRequireTLS")}</Typography>
+						<Switch
+							name="systemEmailRequireTLS"
+							checked={systemEmailRequireTLS}
+							onChange={handleChange}
+						/>
+						<Typography>{t("settingsEmailRejectUnauthorized")}</Typography>
+						<Switch
+							name="systemEmailRejectUnauthorized"
+							checked={systemEmailRejectUnauthorized}
+							onChange={handleChange}
+						/>
+					</Box>
+					<Box>
+						{systemEmailHost &&
+							systemEmailPort &&
+							systemEmailAddress &&
+							systemEmailPassword && (
+								<Button
+									variant="contained"
+									color="accent"
+									loading={isSending}
+									onClick={handleSendTestEmail}
+								>
+									{t("settingsTestEmail", "Send test e-mail")}
+								</Button>
+							)}
 					</Box>
 				</Stack>
 			</Box>
diff --git a/client/src/Pages/Settings/index.jsx b/client/src/Pages/Settings/index.jsx
index a3cd88fca..804ca48c7 100644
--- a/client/src/Pages/Settings/index.jsx
+++ b/client/src/Pages/Settings/index.jsx
@@ -56,17 +56,27 @@ const Settings = () => {
 
 	// Handlers
 	const handleChange = async (e) => {
-		const { name, value } = e.target;
+		const { name, value, checked } = e.target;
 
 		// Special case for showURL until handled properly in the backend
 		if (name === "showURL") {
 			dispatch(setShowURL(value));
 			return;
 		}
+		let newValue;
+		if (
+			name === "systemEmailIgnoreTLS" ||
+			name === "systemEmailRequireTLS" ||
+			name === "systemEmailRejectUnauthorized" ||
+			name === "systemEmailSecure" ||
+			name === "systemEmailPool"
+		) {
+			newValue = checked;
+		}
 		// Build next state early
 		const newSettingsData = {
 			...settingsData,
-			settings: { ...settingsData.settings, [name]: value },
+			settings: { ...settingsData.settings, [name]: newValue ?? value },
 		};
 
 		// Validate
diff --git a/client/src/Utils/NetworkService.js b/client/src/Utils/NetworkService.js
index ecde44a9e..3059462f9 100644
--- a/client/src/Utils/NetworkService.js
+++ b/client/src/Utils/NetworkService.js
@@ -973,10 +973,12 @@ class NetworkService {
 				systemEmailPort: emailConfig.systemEmailPort,
 				systemEmailAddress: emailConfig.systemEmailAddress,
 				systemEmailPassword: emailConfig.systemEmailPassword,
-				// Only include these if they are present
-				...(emailConfig.systemEmailConnectionHost && {
-					systemEmailConnectionHost: emailConfig.systemEmailConnectionHost,
-				}),
+				systemEmailSecure: emailConfig.systemEmailSecure,
+				systemEmailPool: emailConfig.systemEmailPool,
+				systemEmailIgnoreTLS: emailConfig.systemEmailIgnoreTLS,
+				systemEmailRequireTLS: emailConfig.systemEmailRequireTLS,
+				systemEmailRejectUnauthorized: emailConfig.systemEmailRejectUnauthorized,
+				systemEmailTLSServername: emailConfig.systemEmailTLSServername,
 				...(emailConfig.systemEmailUser && {
 					systemEmailUser: emailConfig.systemEmailUser,
 				}),
diff --git a/client/src/Validation/validation.js b/client/src/Validation/validation.js
index 043e88f50..f1811a124 100644
--- a/client/src/Validation/validation.js
+++ b/client/src/Validation/validation.js
@@ -290,10 +290,16 @@ const settingsValidation = joi.object({
 	timezone: joi.string().allow("").optional(),
 	systemEmailHost: joi.string().allow(""),
 	systemEmailPort: joi.number().allow(null, ""),
+	systemEmailSecure: joi.boolean().optional(),
+	systemEmailPool: joi.boolean().optional(),
 	systemEmailAddress: joi.string().allow(""),
 	systemEmailPassword: joi.string().allow(""),
 	systemEmailUser: joi.string().allow(""),
-	systemEmailConnectionHost: joi.string().allow(""),
+	systemEmailConnectionHost: joi.string().allow("").optional(),
+	systemEmailTLSServername: joi.string().allow(""),
+	systemEmailIgnoreTLS: joi.boolean(),
+	systemEmailRequireTLS: joi.boolean(),
+	systemEmailRejectUnauthorized: joi.boolean(),
 });
 
 const dayjsValidator = (value, helpers) => {
diff --git a/client/src/locales/en.json b/client/src/locales/en.json
index bc6c8bbb9..2791dd3e7 100644
--- a/client/src/locales/en.json
+++ b/client/src/locales/en.json
@@ -681,12 +681,18 @@
 	},
 	"settingsEmail": "Email",
 	"settingsEmailDescription": "Configure the email settings for your system. This is used to send notifications and alerts.",
-	"settingsEmailHost": "Email host - Hostname or IP address of the SMTP server",
+	"settingsEmailHost": "Email host - Hostname or IP address to connect to",
 	"settingsEmailPort": "Email port - Port to connect to",
 	"settingsEmailAddress": "Email address - Used for authentication",
 	"settingsEmailPassword": "Email password - Password for authentication",
 	"settingsEmailUser": "Email user - Username for authentication, overrides email address if specified",
 	"settingsEmailFieldResetLabel": "Password is set. Click Reset to change it.",
+	"settingsEmailTLSServername": "TLS Servername - Optional Hostname for TLS Validation when host is an IP",
+	"settingsEmailIgnoreTLS": "Ignore TLS - Disable STARTTLS",
+	"settingsEmailRequireTLS": "Require TLS - Force STARTTLS",
+	"settingsEmailRejectUnauthorized": "Reject Unauthorized",
+	"settingsEmailSecure": "Secure - Use SSL",
+	"settingsEmailPool": "Pool - Enable connection pooling",
 	"state": "State",
 	"statusBreadCrumbsStatusPages": "Status Pages",
 	"statusBreadCrumbsDetails": "Details",
@@ -716,7 +722,7 @@
 	"settingsTestEmailFailed": "Failed to send test email",
 	"settingsTestEmailFailedWithReason": "Failed to send test email: {{reason}}",
 	"settingsTestEmailUnknownError": "Unknown error",
-	"settingsEmailRequiredFields": "Email host and port are required",
+	"settingsEmailRequiredFields": "Email address, host, port and password are required",
 	"statusMsg": {
 		"paused": "Monitoring is paused.",
 		"up": "Your site is up.",
diff --git a/server/controllers/settingsController.js b/server/controllers/settingsController.js
index 58e8ce9f4..d1010c093 100755
--- a/server/controllers/settingsController.js
+++ b/server/controllers/settingsController.js
@@ -74,6 +74,12 @@ class SettingsController {
 				systemEmailPassword,
 				systemEmailUser,
 				systemEmailConnectionHost,
+				systemEmailSecure,
+				systemEmailPool,
+				systemEmailIgnoreTLS,
+				systemEmailRequireTLS,
+				systemEmailRejectUnauthorized,
+				systemEmailTLSServername,
 			} = req.body;
 
 			const subject = this.stringService.testEmailSubject;
@@ -91,6 +97,12 @@ class SettingsController {
 					systemEmailAddress,
 					systemEmailPassword,
 					systemEmailConnectionHost,
+					systemEmailSecure,
+					systemEmailPool,
+					systemEmailIgnoreTLS,
+					systemEmailRequireTLS,
+					systemEmailRejectUnauthorized,
+					systemEmailTLSServername,
 				}
 			);
 
diff --git a/server/db/models/AppSettings.js b/server/db/models/AppSettings.js
index c47de06fa..cd63118e9 100755
--- a/server/db/models/AppSettings.js
+++ b/server/db/models/AppSettings.js
@@ -32,6 +32,29 @@ const AppSettingsSchema = mongoose.Schema(
 			type: String,
 			default: "localhost",
 		},
+		systemEmailTLSServername: {
+			type: String,
+		},
+		systemEmailSecure: {
+			type: Boolean,
+			default: false,
+		},
+		systemEmailPool: {
+			type: Boolean,
+			default: false,
+		},
+		systemEmailIgnoreTLS: {
+			type: Boolean,
+			default: false,
+		},
+		systemEmailRequireTLS: {
+			type: Boolean,
+			default: false,
+		},
+		systemEmailRejectUnauthorized: {
+			type: Boolean,
+			default: true,
+		},
 		singleton: {
 			type: Boolean,
 			required: true,
diff --git a/server/service/emailService.js b/server/service/emailService.js
index 035cc6505..09123ef93 100755
--- a/server/service/emailService.js
+++ b/server/service/emailService.js
@@ -101,39 +101,37 @@ class EmailService {
 		const {
 			systemEmailHost,
 			systemEmailPort,
+			systemEmailSecure,
+			systemEmailPool,
 			systemEmailUser,
 			systemEmailAddress,
 			systemEmailPassword,
 			systemEmailConnectionHost,
+			systemEmailTLSServername,
+			systemEmailIgnoreTLS,
+			systemEmailRequireTLS,
+			systemEmailRejectUnauthorized,
 		} = config;
 
-		const baseEmailConfig = {
+		const emailConfig = {
 			host: systemEmailHost,
-			port: systemEmailPort,
-			secure: true,
+			port: Number(systemEmailPort),
+			secure: systemEmailSecure,
 			auth: {
 				user: systemEmailUser || systemEmailAddress,
 				pass: systemEmailPassword,
 			},
+			name: systemEmailConnectionHost || "localhost",
 			connectionTimeout: 5000,
+			pool: systemEmailPool,
+			tls: {
+				rejectUnauthorized: systemEmailRejectUnauthorized,
+				ignoreTLS: systemEmailIgnoreTLS,
+				requireTLS: systemEmailRequireTLS,
+				servername: systemEmailTLSServername,
+			},
 		};
 
-		const isSmtps = Number(systemEmailPort) === 465;
-
-		const emailConfig = !isSmtps
-			? {
-					...baseEmailConfig,
-					name: systemEmailConnectionHost || "localhost",
-					secure: false,
-					pool: true,
-					tls: { rejectUnauthorized: false },
-				}
-			: baseEmailConfig;
-
-		if (!isSmtps) {
-			delete emailConfig.auth;
-		}
-
 		this.transporter = this.nodemailer.createTransport(emailConfig);
 
 		const buildHtml = async (template, context) => {
diff --git a/server/validation/joi.js b/server/validation/joi.js
index 622cb9148..5eb24e758 100755
--- a/server/validation/joi.js
+++ b/server/validation/joi.js
@@ -410,7 +410,13 @@ const updateAppSettingsBodyValidation = joi.object({
 	systemEmailAddress: joi.string().allow(""),
 	systemEmailPassword: joi.string().allow(""),
 	systemEmailUser: joi.string().allow(""),
-	systemEmailConnectionHost: joi.string().allow(""),
+	systemEmailConnectionHost: joi.string().allow("").optional(),
+	systemEmailTLSServername: joi.string().allow("").optional(),
+	systemEmailSecure: joi.boolean(),
+	systemEmailPool: joi.boolean(),
+	systemEmailIgnoreTLS: joi.boolean(),
+	systemEmailRequireTLS: joi.boolean(),
+	systemEmailRejectUnauthorized: joi.boolean(),
 });
 
 //****************************************
@@ -612,10 +618,16 @@ const sendTestEmailBodyValidation = joi.object({
 	to: joi.string().required(),
 	systemEmailHost: joi.string(),
 	systemEmailPort: joi.number(),
+	systemEmailSecure: joi.boolean(),
+	systemEmailPool: joi.boolean(),
 	systemEmailAddress: joi.string(),
 	systemEmailPassword: joi.string(),
 	systemEmailUser: joi.string(),
-	systemEmailConnectionHost: joi.string(),
+	systemEmailConnectionHost: joi.string().allow("").optional(),
+	systemEmailIgnoreTLS: joi.boolean(),
+	systemEmailRequireTLS: joi.boolean(),
+	systemEmailRejectUnauthorized: joi.boolean(),
+	systemEmailTLSServername: joi.string().allow("").optional(),
 });
 
 export {