diff --git a/StikJIT/StikJITApp.swift b/StikJIT/StikJITApp.swift
index ce72c824..8a1ea003 100644
--- a/StikJIT/StikJITApp.swift
+++ b/StikJIT/StikJITApp.swift
@@ -6,6 +6,7 @@
 //
 
 import SwiftUI
+import Network
 import em_proxy
 import UniformTypeIdentifiers
 
@@ -42,28 +43,44 @@ struct HeartbeatApp: App {
             if isLoading {
                 LoadingView()
                     .onAppear {
+                        if !isConnectedToWifi() {
+                            showAlert(title: "Connection Required",
+                                    message: "Please connect to WiFi to continue",
+                                    showOk: true) { _ in
+                                exit(0)
+                            }
+                            return
+                        }
                         startProxy() { result, error in
                             if result {
-                                if FileManager.default.fileExists(atPath: URL.documentsDirectory.appendingPathComponent("pairingFile.plist").path) {
-                                    Timer.scheduledTimer(withTimeInterval: 0.5, repeats: true) { timer in
-                                        if pubHeartBeat {
-                                            isLoading = false
-                                            timer.invalidate()
-                                        } else {
-                                            if let error {
-                                                if error == InvalidHostID.rawValue {
-                                                    isPairing = true
+                                checkVPNConnection() { result, vpn_error in
+                                    if result {
+                                        if FileManager.default.fileExists(atPath: URL.documentsDirectory.appendingPathComponent("pairingFile.plist").path) {
+                                            Timer.scheduledTimer(withTimeInterval: 0.5, repeats: true) { timer in
+                                                if pubHeartBeat {
+                                                    isLoading = false
+                                                    timer.invalidate()
                                                 } else {
-                                                    startHeartbeatInBackground()
+                                                    if let error {
+                                                        if error == InvalidHostID.rawValue {
+                                                            isPairing = true
+                                                        } else {
+                                                            startHeartbeatInBackground()
+                                                        }
+                                                        self.error = nil
+                                                    }
                                                 }
-                                                self.error = nil
                                             }
+                                            
+                                            startHeartbeatInBackground()
+                                        } else {
+                                            isLoading = false
+                                        }
+                                    } else if let vpn_error {
+                                        showAlert(title: "Error", message: "EM Proxy failed to connect: \(vpn_error)", showOk: true) { _ in
+                                            exit(0)
                                         }
                                     }
-                                    
-                                    startHeartbeatInBackground()
-                                } else {
-                                    isLoading = false
                                 }
                             } else if let error {
                                 showAlert(title: "Error", message: "EM Proxy Failed to start \(error)", showOk: true) { cool in
@@ -137,6 +154,84 @@ struct HeartbeatApp: App {
             }
         }
     }
+    
+    private func checkVPNConnection(callback: @escaping (Bool, String?) -> Void) {
+        let host = NWEndpoint.Host("10.7.0.1")
+        let port = NWEndpoint.Port(rawValue: 62078)!
+        
+        let connection = NWConnection(host: host, port: port, using: .tcp)
+        
+        // Create a variable to hold the timeout work item
+        var timeoutWorkItem: DispatchWorkItem?
+        
+        timeoutWorkItem = DispatchWorkItem { [weak connection] in
+            if connection?.state != .ready {
+                connection?.cancel()
+                DispatchQueue.main.async {
+                    // Only call back if we haven't already
+                    if timeoutWorkItem?.isCancelled == false {
+                        callback(false, "[TIMEOUT] Wireguard is not connected. Try closing this app, turn Wireguard off and back on.")
+                    }
+                }
+            }
+        }
+        
+        connection.stateUpdateHandler = { [weak connection] state in
+            switch state {
+            case .ready:
+                // Connection succeeded - cancel the timeout
+                timeoutWorkItem?.cancel()
+                connection?.cancel()
+                DispatchQueue.main.async {
+                    callback(true, nil)
+                }
+            case .failed(let error):
+                // Connection failed - cancel the timeout
+                timeoutWorkItem?.cancel()
+                connection?.cancel()
+                DispatchQueue.main.async {
+                    if error == NWError.posix(.ETIMEDOUT) {
+                        callback(false, "Wireguard is not connected. Try closing the app, turn it off and back on.")
+                    } else if error == NWError.posix(.ECONNREFUSED) {
+                        callback(false, "Wifi is not connected. StikJIT won't work on cellular data.")
+                    } else {
+                        callback(false, "em proxy check error: \(error.localizedDescription)")
+                    }
+                }
+            default:
+                break
+            }
+        }
+        
+        // Start the connection
+        connection.start(queue: .global())
+        
+        // Schedule the timeout
+        if let workItem = timeoutWorkItem {
+            DispatchQueue.global().asyncAfter(deadline: .now() + 20, execute: workItem)
+        }
+    }
+    
+    func isConnectedToWifi() -> Bool {
+        var isWifi = false
+            let monitor = NWPathMonitor(requiredInterfaceType: .wifi)
+            let semaphore = DispatchSemaphore(value: 0)
+            
+            monitor.pathUpdateHandler = { path in
+                isWifi = path.status == .satisfied
+                semaphore.signal()
+            }
+            
+            let queue = DispatchQueue(label: "WiFiCheckQueue")
+            monitor.start(queue: queue)
+            
+            // Wait for the result with a timeout to avoid hanging
+            let result = semaphore.wait(timeout: .now() + 2)
+            monitor.cancel()
+            
+            // Return false if we timed out
+            return result == .success && isWifi
+    }
 }
 
 var pubHeartBeat = false
diff --git a/StikJIT/idevice/heartbeat.c b/StikJIT/idevice/heartbeat.c
index e44b9f62..bd96c679 100644
--- a/StikJIT/idevice/heartbeat.c
+++ b/StikJIT/idevice/heartbeat.c
@@ -19,12 +19,11 @@ void startHeartbeat(IdevicePairingFile* pairing_file, TcpProviderHandle** provid
     struct sockaddr_in addr;
     memset(&addr, 0, sizeof(addr));
     addr.sin_family = AF_INET;
-    addr.sin_port = htons(LOCKDOWN_PORT);
     if (inet_pton(AF_INET, "10.7.0.1", &addr.sin_addr) <= 0) {
         logger("DEBUG: Error converting IP address.");
         return;
     }
-    logger("DEBUG: Socket address created for IP 10.7.0.1 on port %d.", LOCKDOWN_PORT);
+    logger("DEBUG: Socket address created for IP 10.7.0.1");
     
     IdeviceErrorCode err = IdeviceSuccess;
     
@@ -38,7 +37,7 @@ void startHeartbeat(IdevicePairingFile* pairing_file, TcpProviderHandle** provid
     }
     logger("DEBUG: TCP provider created successfully.");
     
-    logger("DEBUG: Connecting to installation proxy...");
+    logger("DEBUG: Connecting to heartbeat...");
     HeartbeatClientHandle *client = NULL;
     err = heartbeat_connect_tcp(*provider, &client);
     if (err != IdeviceSuccess) {
@@ -46,7 +45,7 @@ void startHeartbeat(IdevicePairingFile* pairing_file, TcpProviderHandle** provid
         logger("DEBUG: Failed to connect to installation proxy: %d", err);
         return;
     }
-    logger("DEBUG: Connected to installation proxy successfully.");
+    logger("DEBUG: Connected to heartbeat successfully.");
     
     completion(0, "Heartbeat Completed");