diff --git a/server/model/monitor.js b/server/model/monitor.js
index 75af6b813..97926f4c7 100644
--- a/server/model/monitor.js
+++ b/server/model/monitor.js
@@ -8,7 +8,7 @@ const { log, UP, DOWN, PENDING, MAINTENANCE, flipStatus, MAX_INTERVAL_SECOND, MI
     PING_COUNT_MIN, PING_COUNT_MAX, PING_COUNT_DEFAULT,
     PING_PER_REQUEST_TIMEOUT_MIN, PING_PER_REQUEST_TIMEOUT_MAX, PING_PER_REQUEST_TIMEOUT_DEFAULT
 } = require("../../src/util");
-const { tcping, ping, checkCertificate, checkStatusCode, getTotalClientInRoom, setting, mssqlQuery, postgresQuery, mysqlQuery, setSetting, httpNtlm, radius, grpcQuery,
+const { ping, checkCertificate, checkStatusCode, getTotalClientInRoom, setting, mssqlQuery, postgresQuery, mysqlQuery, setSetting, httpNtlm, radius, grpcQuery,
     kafkaProducerAsync, getOidcTokenClientCredentials, rootCertificatesFingerprints, axiosAbortSignal
 } = require("../util-server");
 const { R } = require("redbean-node");
@@ -621,11 +621,6 @@ class Monitor extends BeanModel {
 
                     }
 
-                } else if (this.type === "port") {
-                    bean.ping = await tcping(this.hostname, this.port);
-                    bean.msg = "";
-                    bean.status = UP;
-
                 } else if (this.type === "ping") {
                     bean.ping = await ping(this.hostname, this.ping_count, "", this.ping_numeric, this.packetSize, this.timeout, this.ping_per_request_timeout);
                     bean.msg = "";
diff --git a/server/monitor-types/tcp.js b/server/monitor-types/tcp.js
new file mode 100644
index 000000000..f0bc12a01
--- /dev/null
+++ b/server/monitor-types/tcp.js
@@ -0,0 +1,158 @@
+const { MonitorType } = require("./monitor-type");
+const { UP, DOWN, PING_GLOBAL_TIMEOUT_DEFAULT: TIMEOUT, log } = require("../../src/util");
+const { checkCertificate } = require("../util-server");
+const tls = require("tls");
+const net = require("net");
+const tcpp = require("tcp-ping");
+
+/**
+ * Send TCP request to specified hostname and port
+ * @param {string} hostname Hostname / address of machine
+ * @param {number} port TCP port to test
+ * @returns {Promise<number>} Maximum time in ms rounded to nearest integer
+ */
+const tcping = (hostname, port) => {
+    return new Promise((resolve, reject) => {
+        tcpp.ping(
+            {
+                address: hostname,
+                port: port,
+                attempts: 1,
+            },
+            (err, data) => {
+                if (err) {
+                    reject(err);
+                }
+
+                if (data.results.length >= 1 && data.results[0].err) {
+                    reject(data.results[0].err);
+                }
+
+                resolve(Math.round(data.max));
+            }
+        );
+    });
+};
+
+class TCPMonitorType extends MonitorType {
+    name = "port";
+
+    /**
+     * @inheritdoc
+     */
+    async check(monitor, heartbeat, _server) {
+        try {
+            const resp = await tcping(monitor.hostname, monitor.port);
+            heartbeat.ping = resp;
+            heartbeat.msg = `${resp} ms`;
+            heartbeat.status = UP;
+        } catch {
+            heartbeat.status = DOWN;
+            heartbeat.msg = "Connection failed";
+            return;
+        }
+
+        let socket_;
+
+        const preTLS = () =>
+            new Promise((resolve, reject) => {
+                let timeout;
+                socket_ = net.connect(monitor.port, monitor.hostname);
+
+                const onTimeout = () => {
+                    log.debug(this.name, `[${monitor.name}] Pre-TLS connection timed out`);
+                    reject("Connection timed out");
+                };
+
+                socket_.on("connect", () => {
+                    log.debug(this.name, `[${monitor.name}] Pre-TLS connection: ${JSON.stringify(socket_)}`);
+                });
+
+                socket_.on("data", data => {
+                    const response = data.toString();
+                    const response_ = response.toLowerCase();
+                    log.debug(this.name, `[${monitor.name}] Pre-TLS response: ${response}`);
+                    switch (true) {
+                        case response_.includes("start tls") || response_.includes("begin tls"):
+                            timeout && clearTimeout(timeout);
+                            resolve({ socket: socket_ });
+                            break;
+                        case response.startsWith("* OK") || response.match(/CAPABILITY.+STARTTLS/):
+                            socket_.write("a001 STARTTLS\r\n");
+                            break;
+                        case response.startsWith("220") || response.includes("ESMTP"):
+                            socket_.write(`EHLO ${monitor.hostname}\r\n`);
+                            break;
+                        case response.includes("250-STARTTLS"):
+                            socket_.write("STARTTLS\r\n");
+                            break;
+                        default:
+                            reject(`Unexpected response: ${response}`);
+                    }
+                });
+                socket_.on("error", error => {
+                    log.debug(this.name, `[${monitor.name}] ${error.toString()}`);
+                    reject(error);
+                });
+                socket_.setTimeout(1000 * TIMEOUT, onTimeout);
+                timeout = setTimeout(onTimeout, 1000 * TIMEOUT);
+            });
+
+        const reuseSocket = monitor.smtpSecurity === "starttls" ? await preTLS() : {};
+
+        if ([ "secure", "starttls" ].includes(monitor.smtpSecurity) && monitor.isEnabledExpiryNotification()) {
+            let socket = null;
+            try {
+                const options = {
+                    host: monitor.hostname,
+                    port: monitor.port,
+                    servername: monitor.hostname,
+                    ...reuseSocket,
+                };
+
+                const tlsInfoObject = await new Promise((resolve, reject) => {
+                    socket = tls.connect(options);
+
+                    socket.on("secureConnect", () => {
+                        try {
+                            const info = checkCertificate(socket);
+                            resolve(info);
+                        } catch (error) {
+                            reject(error);
+                        }
+                    });
+
+                    socket.on("error", error => {
+                        reject(error);
+                    });
+
+                    socket.setTimeout(1000 * TIMEOUT, () => {
+                        reject(new Error("Connection timed out"));
+                    });
+                });
+
+                await monitor.handleTlsInfo(tlsInfoObject);
+                if (!tlsInfoObject.valid) {
+                    heartbeat.status = DOWN;
+                    heartbeat.msg = "Certificate is invalid";
+                }
+            } catch (error) {
+                const message = error instanceof Error ? error.message : "Unknown error";
+                heartbeat.status = DOWN;
+                heartbeat.msg = `TLS Connection failed: ${message}`;
+            } finally {
+                if (socket && !socket.destroyed) {
+                    socket.end();
+                }
+            }
+        }
+
+        if (socket_ && !socket_.destroyed) {
+            socket_.end();
+        }
+    }
+}
+
+module.exports = {
+    TCPMonitorType,
+};
diff --git a/server/uptime-kuma-server.js b/server/uptime-kuma-server.js
index 3c84bf646..b95477664 100644
--- a/server/uptime-kuma-server.js
+++ b/server/uptime-kuma-server.js
@@ -118,6 +118,7 @@ class UptimeKumaServer {
         UptimeKumaServer.monitorTypeList["snmp"] = new SNMPMonitorType();
         UptimeKumaServer.monitorTypeList["mongodb"] = new MongodbMonitorType();
         UptimeKumaServer.monitorTypeList["rabbitmq"] = new RabbitMqMonitorType();
+        UptimeKumaServer.monitorTypeList["port"] = new TCPMonitorType();
         UptimeKumaServer.monitorTypeList["manual"] = new ManualMonitorType();
         UptimeKumaServer.monitorTypeList["redis"] = new RedisMonitorType();
 
@@ -560,6 +561,7 @@ const { GroupMonitorType } = require("./monitor-types/group");
 const { SNMPMonitorType } = require("./monitor-types/snmp");
 const { MongodbMonitorType } = require("./monitor-types/mongodb");
 const { RabbitMqMonitorType } = require("./monitor-types/rabbitmq");
+const { TCPMonitorType } = require("./monitor-types/tcp.js");
 const { ManualMonitorType } = require("./monitor-types/manual");
 const { RedisMonitorType } = require("./monitor-types/redis");
 const Monitor = require("./model/monitor");
diff --git a/server/util-server.js b/server/util-server.js
index 3de6e777f..6365b623c 100644
--- a/server/util-server.js
+++ b/server/util-server.js
@@ -1,4 +1,3 @@
-const tcpp = require("tcp-ping");
 const ping = require("@louislam/ping");
 const { R } = require("redbean-node");
 const {
@@ -98,33 +97,6 @@ exports.getOidcTokenClientCredentials = async (tokenEndpoint, clientId, clientSe
     return await client.grant(grantParams);
 };
 
-/**
- * Send TCP request to specified hostname and port
- * @param {string} hostname Hostname / address of machine
- * @param {number} port TCP port to test
- * @returns {Promise<number>} Maximum time in ms rounded to nearest integer
- */
-exports.tcping = function (hostname, port) {
-    return new Promise((resolve, reject) => {
-        tcpp.ping({
-            address: hostname,
-            port: port,
-            attempts: 1,
-        }, function (err, data) {
-
-            if (err) {
-                reject(err);
-            }
-
-            if (data.results.length >= 1 && data.results[0].err) {
-                reject(data.results[0].err);
-            }
-
-            resolve(Math.round(data.max));
-        });
-    });
-};
-
 /**
  * Ping the specified machine
  * @param {string} destAddr Hostname / IP address of machine to ping
diff --git a/src/pages/EditMonitor.vue b/src/pages/EditMonitor.vue
index b5213ef5e..798c89f17 100644
--- a/src/pages/EditMonitor.vue
+++ b/src/pages/EditMonitor.vue
@@ -366,6 +366,15 @@
                                 </div>
                             </div>
 
+                            <div v-if="monitor.type === 'port'" class="my-3">
+                                <label for="port_security" class="form-label">{{ $t("SSL/TLS") }}</label>
+                                <select id="port_security" v-model="monitor.smtpSecurity" class="form-select">
+                                    <option value="nostarttls">None</option>
+                                    <option value="secure">SSL</option>
+                                    <option value="starttls">STARTTLS</option>
+                                </select>
+                            </div>
+
                             <!-- Json Query -->
                             <!-- For Json Query / SNMP -->
                             <div v-if="monitor.type === 'json-query' || monitor.type === 'snmp'" class="my-3">
@@ -671,7 +680,7 @@
 
                             <h2 v-if="monitor.type !== 'push'" class="mt-5 mb-2">{{ $t("Advanced") }}</h2>
 
-                            <div v-if="monitor.type === 'http' || monitor.type === 'keyword' || monitor.type === 'json-query' " class="my-3 form-check" :title="monitor.ignoreTls ? $t('ignoredTLSError') : ''">
+                            <div v-if="monitor.type === 'http' || monitor.type === 'keyword' || monitor.type === 'json-query' || (monitor.type === 'port' && ['starttls', 'secure'].includes(monitor.smtpSecurity))" class="my-3 form-check" :title="monitor.ignoreTls ? $t('ignoredTLSError') : ''">
                                 <input id="expiry-notification" v-model="monitor.expiryNotification" class="form-check-input" type="checkbox" :disabled="monitor.ignoreTls">
                                 <label class="form-check-label" for="expiry-notification">
                                     {{ $t("Certificate Expiry Notification") }}
diff --git a/test/backend-test/test-tcp.js b/test/backend-test/test-tcp.js
new file mode 100644
index 000000000..3d389c154
--- /dev/null
+++ b/test/backend-test/test-tcp.js
@@ -0,0 +1,182 @@
+const { describe, test } = require("node:test");
+const assert = require("node:assert");
+const { TCPMonitorType } = require("../../server/monitor-types/tcp");
+const { UP, DOWN, PENDING } = require("../../src/util");
+const net = require("net");
+
+/**
+ * Test suite for TCP Monitor functionality
+ * This test suite checks the behavior of the TCPMonitorType class
+ * under different network connection scenarios.
+ */
+describe("TCP Monitor", () => {
+    /**
+     * Creates a TCP server on a specified port
+     * @param {number} port - The port number to listen on
+     * @returns {Promise<net.Server>} A promise that resolves with the created server
+     */
+    async function createTCPServer(port) {
+        return new Promise((resolve, reject) => {
+            const server = net.createServer();
+
+            server.listen(port, () => {
+                resolve(server);
+            });
+
+            server.on("error", err => {
+                reject(err);
+            });
+        });
+    }
+
+    /**
+     * Test case to verify TCP monitor works when a server is running
+     * Checks that the monitor correctly identifies an active TCP server
+     */
+    test("TCP server is running", async () => {
+        const port = 12345;
+        const server = await createTCPServer(port);
+
+        try {
+            const tcpMonitor = new TCPMonitorType();
+
+            const monitor = {
+                hostname: "localhost",
+                port: port,
+                isEnabledExpiryNotification: () => false,
+            };
+
+            const heartbeat = {
+                msg: "",
+                status: PENDING,
+            };
+
+            await tcpMonitor.check(monitor, heartbeat, {});
+
+            assert.strictEqual(heartbeat.status, UP);
+        } finally {
+            server.close();
+        }
+    });
+
+    /**
+     * Test case to verify TCP monitor handles non-running servers
+     * Checks that the monitor correctly identifies an inactive TCP server
+     */
+    test("TCP server is not running", async () => {
+        const tcpMonitor = new TCPMonitorType();
+
+        const monitor = {
+            hostname: "localhost",
+            port: 54321,
+            isEnabledExpiryNotification: () => false,
+        };
+
+        const heartbeat = {
+            msg: "",
+            status: PENDING,
+        };
+
+        await tcpMonitor.check(monitor, heartbeat, {});
+
+        assert.strictEqual(heartbeat.status, DOWN);
+    });
+
+    /**
+     * Test case to verify TCP monitor handles servers with expired or invalid TLS certificates
+     * Checks that the monitor correctly identifies TLS certificate issues
+     */
+    test("TCP server with expired or invalid TLS certificate", async t => {
+        const tcpMonitor = new TCPMonitorType();
+
+        const monitor = {
+            hostname: "expired.badssl.com",
+            port: 443,
+            smtpSecurity: "secure",
+            isEnabledExpiryNotification: () => true,
+            handleTlsInfo: async tlsInfo => {
+                return tlsInfo;
+            },
+        };
+
+        const heartbeat = {
+            msg: "",
+            status: PENDING,
+        };
+
+        await tcpMonitor.check(monitor, heartbeat, {});
+
+        assert.strictEqual(heartbeat.status, DOWN);
+        assert([ "Certificate is invalid", "TLS Connection failed:" ].some(prefix => heartbeat.msg.startsWith(prefix)));
+    });
+
+    test("TCP server with valid TLS certificate (SSL)", async t => {
+        const tcpMonitor = new TCPMonitorType();
+
+        const monitor = {
+            hostname: "smtp.gmail.com",
+            port: 465,
+            smtpSecurity: "secure",
+            isEnabledExpiryNotification: () => true,
+            handleTlsInfo: async tlsInfo => {
+                return tlsInfo;
+            },
+        };
+
+        const heartbeat = {
+            msg: "",
+            status: PENDING,
+        };
+
+        await tcpMonitor.check(monitor, heartbeat, {});
+
+        assert.strictEqual(heartbeat.status, UP);
+    });
+
+    test("TCP server with valid TLS certificate (STARTTLS)", async t => {
+        const tcpMonitor = new TCPMonitorType();
+
+        const monitor = {
+            hostname: "smtp.gmail.com",
+            port: 587,
+            smtpSecurity: "starttls",
+            isEnabledExpiryNotification: () => true,
+            handleTlsInfo: async tlsInfo => {
+                return tlsInfo;
+            },
+        };
+
+        const heartbeat = {
+            msg: "",
+            status: PENDING,
+        };
+
+        await tcpMonitor.check(monitor, heartbeat, {});
+
+        assert.strictEqual(heartbeat.status, UP);
+    });
+
+    test("TCP server with valid but name mismatching TLS certificate (STARTTLS)", async t => {
+        const tcpMonitor = new TCPMonitorType();
+
+        const monitor = {
+            hostname: "wr-in-f108.1e100.net",
+            port: 587,
+            smtpSecurity: "starttls",
+            isEnabledExpiryNotification: () => true,
+            handleTlsInfo: async tlsInfo => {
+                return tlsInfo;
+            },
+        };
+
+        const heartbeat = {
+            msg: "",
+            status: PENDING,
+        };
+
+        await tcpMonitor.check(monitor, heartbeat, {});
+
+        assert.strictEqual(heartbeat.status, DOWN);
+        assert([ "does not match certificate" ].some(msg => heartbeat.msg.includes(msg)));
+    });
+});