diff --git a/src/electron/vpn.ts b/src/electron/vpn.ts
index 0a04be7..bcbcf71 100644
--- a/src/electron/vpn.ts
+++ b/src/electron/vpn.ts
@@ -68,12 +68,62 @@ function getWireGuardInstallerPath(): string {
 //   throw new Error("Unsupported OS");
 // }
 
+// export async function getConfigPath(): Promise<string> {
+//   if (process.platform !== "win32") {
+//     throw new Error("Only Windows supported for dynamic WireGuard config");
+//   }
+//   console.log("Calling http://35.95.209.161/api/v1/vpn/connect")
+//   // 1️⃣ Call API to get dynamic config
+//   let response = null;
+//   try {
+//     response = await axios.post(
+//       "http://35.95.209.161/api/v1/vpn/connect",
+//       {},
+//       { timeout: 15000 }
+//     );
+//   } catch (err: any) {
+//     console.error("VPN API error:", {
+//       message: err.message,
+//       code: err.code,
+//       response: err.response?.data,
+//     });
+//     throw err;
+//   }
+//   console.log("Called http://35.95.209.161/api/v1/vpn/connect", JSON.stringify(response.data));
+
+//   if (!response.data?.success || !response.data.clientConf) {
+//     throw new Error("Invalid VPN config response");
+//   }
+
+//   const clientConf: string = response.data.clientConf;
+
+//   // 2️⃣ Decide base directory (same idea as your existing logic)
+//   const base = isDev()
+//     ? path.join(process.cwd(), "resources", "wireguard", "windows")
+//     : path.join(process.resourcesPath, "wireguard", "windows");
+
+//   // Ensure directory exists
+//   fs.mkdirSync(base, { recursive: true });
+
+//   // 3️⃣ Create temp / runtime conf file
+//   // IMPORTANT: name must stay stable (WireGuard service name depends on it)
+//   const confPath = path.join(base, "wg0.conf");
+
+//   // 4️⃣ Write config to file
+//   fs.writeFileSync(confPath, clientConf, {
+//     encoding: "utf-8",
+//     mode: 0o600, // secure permissions
+//   });
+
+//   console.log("VPN config written to:", confPath);
+//   // 5️⃣ Return path (same contract as before)
+//   return confPath;
+// }
+
 export async function getConfigPath(): Promise<string> {
-  if (process.platform !== "win32") {
-    throw new Error("Only Windows supported for dynamic WireGuard config");
-  }
-  console.log("Calling http://35.95.209.161/api/v1/vpn/connect")
-  // 1️⃣ Call API to get dynamic config
+  console.log("Calling API: http://35.95.209.161/api/v1/vpn/connect");
+
+  // Fetch dynamic config from server (works for both Windows & macOS)
   let response = null;
   try {
     response = await axios.post(
@@ -89,7 +139,6 @@ export async function getConfigPath(): Promise<string> {
     });
     throw err;
   }
-  console.log("Called http://35.95.209.161/api/v1/vpn/connect", JSON.stringify(response.data));
 
   if (!response.data?.success || !response.data.clientConf) {
     throw new Error("Invalid VPN config response");
@@ -97,29 +146,48 @@ export async function getConfigPath(): Promise<string> {
 
   const clientConf: string = response.data.clientConf;
 
-  // 2️⃣ Decide base directory (same idea as your existing logic)
-  const base = isDev()
-    ? path.join(process.cwd(), "resources", "wireguard", "windows")
-    : path.join(process.resourcesPath, "wireguard", "windows");
+  // ---------- PLATFORM SPECIFIC OUTPUT DIRECTORY ----------
+  let base = "";
+
+  if (process.platform === "win32") {
+    base = isDev()
+      ? path.join(process.cwd(), "resources", "wireguard", "windows")
+      : path.join(process.resourcesPath, "wireguard", "windows");
+  }
+
+  // if (process.platform === "darwin") {
+  //   base = isDev()
+  //     ? path.join(process.cwd(), "resources", "wireguard", "macos")
+  //     : path.join(process.resourcesPath, "wireguard", "macos");
+  // }
+
+  if (process.platform === "darwin") {
+    const base = "/usr/local/etc/wireguard";
+    fs.mkdirSync(base, { recursive: true });
+
+    const confPath = path.join(base, "wg0.conf");
+    fs.writeFileSync(confPath, clientConf, { encoding: "utf8", mode: 0o600 });
+
+    return confPath;
+  }
+
+
+  if (!base) throw new Error("Unsupported OS");
 
-  // Ensure directory exists
   fs.mkdirSync(base, { recursive: true });
 
-  // 3️⃣ Create temp / runtime conf file
-  // IMPORTANT: name must stay stable (WireGuard service name depends on it)
   const confPath = path.join(base, "wg0.conf");
 
-  // 4️⃣ Write config to file
   fs.writeFileSync(confPath, clientConf, {
     encoding: "utf-8",
-    mode: 0o600, // secure permissions
+    mode: 0o600,
   });
 
-  console.log("VPN config written to:", confPath);
-  // 5️⃣ Return path (same contract as before)
+  console.log("Dynamic VPN config saved:", confPath);
   return confPath;
 }
 
+
 // Detect installed WireGuard.exe on Windows
 function findWireGuardCLI(): string | null {
   const possiblePaths = [
@@ -196,6 +264,80 @@ async function ensureWireGuardInstalled(): Promise<string> {
 //   });
 // }
 
+//
+// ------------------ HEALTH + STATUS HELPERS ------------------
+//
+
+// 1️⃣ Check if wg0 interface exists (works for mac + windows)
+async function isTunnelActive(): Promise<boolean> {
+  console.log("🔍 Checking if VPN tunnel is active...");
+
+  try {
+    // ---------------------- macOS ----------------------
+    if (process.platform === "darwin") {
+      console.log("🖥 Platform: macOS — detecting WireGuard via utun interface...");
+
+      const netOutput = await execPromise(`ifconfig`);
+      console.log("📡 ifconfig output length:", netOutput.length);
+
+      const utunMatch = netOutput.match(/utun\d+/);
+      console.log("🔎 utun interface detected:", utunMatch);
+
+      if (utunMatch) {
+        console.log("✅ VPN tunnel ACTIVE (utun interface exists)");
+        return true;
+      } else {
+        console.log("❌ VPN tunnel NOT active (no utun interface found)");
+        return false;
+      }
+    }
+
+    // ---------------------- Windows ----------------------
+    if (process.platform === "win32") {
+      console.log("🖥 Platform: Windows — detecting WireGuard via wg show...");
+
+      const wgOutput = await execPromise(`wg show 2>&1`);
+      console.log("📡 wg show output length:", wgOutput.length);
+
+      const interfaceFound = wgOutput.includes("interface: wg0");
+      console.log("🔎 wg0 interface detected:", interfaceFound);
+
+      if (interfaceFound) {
+        console.log("✅ VPN tunnel ACTIVE (wg0 found)");
+        return true;
+      } else {
+        console.log("❌ VPN tunnel NOT active (wg0 not found)");
+        return false;
+      }
+    }
+
+    // ---------------------- Unsupported OS ----------------------
+    console.log("⚠️ Unsupported OS platform — cannot detect VPN state");
+    return false;
+
+  } catch (err: any) {
+    console.log("❌ isTunnelActive() failed:", err);
+    return false;
+  }
+}
+
+
+// 2️⃣ Check endpoint health
+async function isTunnelHealthy(): Promise<boolean> {
+  try {
+    const response = await axios.get("http://10.0.0.1/health", { timeout: 2000 });
+    return !!response.data?.success;
+  } catch {
+    return false;
+  }
+}
+
+// 3️⃣ Download config only if needed
+async function ensureConfig(platform: string): Promise<string> {
+  return await getConfigPath(); // uses dynamic logic already
+}
+
+
 
 async function connectWindows(): Promise<string> {
 
@@ -294,63 +436,188 @@ async function ensureWireGuardMac(): Promise<void> {
 // --------------- MAC CONNECT/DISCONNECT ---------------
 //
 
+// async function connectMac(): Promise<string> {
+//   const conf = getConfigPath();
+
+//   // Wrap command in login shell so Homebrew paths are available
+//   const cmd = `/bin/bash -l -c "/opt/homebrew/bin/wg-quick up '${conf}'"`;
+
+//   const script = `
+// do shell script "${cmd}" with administrator privileges
+// `;
+//   const escapedScript = script.replace(/\n/g, " ");
+
+//   return execPromise(`osascript -e '${escapedScript}'`)
+//     .then(() => "macOS VPN connected (wg-quick)")
+//     .catch(err => {
+//       throw new Error("macOS VPN connect failed: " + err);
+//     });
+// }
+
+// async function connectMac(): Promise<string> {
+//   try {
+//     const conf = await getConfigPath();
+//     console.log("Configuration Path:", conf);  // Debug the path
+
+//     const cmd = `/bin/bash -l -c "/opt/homebrew/bin/wg-quick up '${conf}'"`;
+
+//     const script = `
+//     do shell script "${cmd}" with administrator privileges
+//     `;
+//     const escapedScript = script.replace(/\n/g, " ");
+
+//     await execPromise(`osascript -e '${escapedScript}'`);
+
+//     return "macOS VPN connected (wg-quick)";
+//   } catch (err) {
+//     console.error("macOS VPN connect failed:", err);
+//     throw new Error("macOS VPN connect failed: " + err);
+//   }
+// }
+
+
+// async function connectMac(): Promise<string> {
+//   await ensureWireGuardMac();
+
+//   const conf = await getConfigPath();
+
+//   const cmd = `/bin/bash -c "sudo /opt/homebrew/bin/wg-quick up '${conf}'"`;
+
+//   try {
+//     await execPromise(cmd);
+//     return "macOS VPN connected";
+//   } catch (err: any) {
+//     throw new Error("macOS VPN connect failed: " + err.message);
+//   }
+// }
 async function connectMac(): Promise<string> {
-  const conf = getConfigPath();
+  await ensureWireGuardMac();
 
-  // Wrap command in login shell so Homebrew paths are available
-  const cmd = `/bin/bash -l -c "/opt/homebrew/bin/wg-quick up '${conf}'"`;
+  const conf = await getConfigPath();
 
-  const script = `
-do shell script "${cmd}" with administrator privileges
-`;
-  const escapedScript = script.replace(/\n/g, " ");
+  // Detect the correct wg-quick binary
+  let wgPath = (await execPromise(`which wg-quick`)).trim();
 
-  return execPromise(`osascript -e '${escapedScript}'`)
-    .then(() => "macOS VPN connected (wg-quick)")
-    .catch(err => {
-      throw new Error("macOS VPN connect failed: " + err);
-    });
+  const cmd = `do shell script "${wgPath} up '${conf}'" with administrator privileges`;
+
+  try {
+    const result = await execPromise(`osascript -e '${cmd}'`);
+    console.log("macOS wg-quick result:", result);
+    return "macOS VPN connected";
+  } catch (err: any) {
+    console.error("macOS VPN connect failed:", err);
+    throw new Error("macOS VPN connect failed: " + err);
+  }
 }
 
 
 
 
-function disconnectMac(): Promise<string> {
-  const cmd = `/bin/bash -l -c "/opt/homebrew/bin/wg-quick down wg0"`;
 
-  const script = `
-do shell script "${cmd}" with administrator privileges
-`;
-  const escapedScript = script.replace(/\n/g, " ");
 
-  return execPromise(`osascript -e '${escapedScript}'`)
-    .then(() => "macOS VPN disconnected")
-    .catch(err => {
-      throw new Error("macOS VPN disconnect failed: " + err);
-    });
+
+
+// function disconnectMac(): Promise<string> {
+//   const cmd = `/bin/bash -l -c "/opt/homebrew/bin/wg-quick down wg0"`;
+
+//   const script = `
+// do shell script "${cmd}" with administrator privileges
+// `;
+//   const escapedScript = script.replace(/\n/g, " ");
+
+//   return execPromise(`osascript -e '${escapedScript}'`)
+//     .then(() => "macOS VPN disconnected")
+//     .catch(err => {
+//       throw new Error("macOS VPN disconnect failed: " + err);
+//     });
+// }
+
+// function disconnectMac(): Promise<string> {
+//   const cmd = `/bin/bash -c "sudo /opt/homebrew/bin/wg-quick down wg0"`;
+
+//   return execPromise(cmd)
+//     .then(() => "macOS VPN disconnected")
+//     .catch(err => {
+//       throw new Error("macOS VPN disconnect failed: " + err.message);
+//     });
+// }
+
+
+
+async function disconnectMac(): Promise<string> {
+  let wgPath = (await execPromise(`which wg-quick`)).trim();
+
+  const cmd = `do shell script "${wgPath} down wg0" with administrator privileges`;
+
+  try {
+    await execPromise(`osascript -e '${cmd}'`);
+    return "macOS VPN disconnected";
+  } catch (err: any) {
+    throw new Error("macOS VPN disconnect failed: " + err);
+  }
 }
 
 
 
 
+
+
 //
 // ------------------ PUBLIC API ------------------
 //
 
-export function startVPN(): Promise<string> {
+export async function startVPN(): Promise<string> {
   const platform = os.platform();
 
-  if (platform === "win32") return connectWindows();
-  if (platform === "darwin") return connectMac();
+  if (platform !== "win32" && platform !== "darwin") {
+    throw new Error("Unsupported OS");
+  }
 
-  return Promise.reject("Unsupported OS");
+  // STEP 1: tunnel active?
+  console.log("Start VPN Called for pltf :", platform)
+  const active = await isTunnelActive();
+  console.log("VPN Active Status :", active)
+
+  if (active) {
+    console.log("VPN already active — checking health...");
+
+    // STEP 2: healthy?
+    if (await isTunnelHealthy()) {
+      console.log("VPN healthy — skip reconnect");
+      return "VPN already connected and healthy";
+    }
+
+    console.log("VPN active but unhealthy — reconnecting...");
+    await stopVPN(); // gracefully disconnect
+  }
+
+  // STEP 3: ensure config before connect
+  await ensureConfig(platform);
+
+  // STEP 4: connect
+  if (platform === "win32") {
+    return connectWindows();
+  }
+
+  if (platform === "darwin") {
+    return connectMac();
+  }
+
+  // STEP 5: unreachable fallback to satisfy TS
+  throw new Error("Unexpected platform state");
 }
 
-export function stopVPN(): Promise<string> {
+
+export async function stopVPN(): Promise<string> {
   const platform = os.platform();
 
-  if (platform === "win32") return disconnectWindows();
-  if (platform === "darwin") return disconnectMac();
+  try {
+    if (platform === "win32") return await disconnectWindows();
+    if (platform === "darwin") return await disconnectMac();
+  } catch {
+    return "VPN not running";
+  }
 
-  return Promise.reject("Unsupported OS");
+  throw new Error("Unsupported OS");
 }
+
diff --git a/src/ui/pages/Vpn/VpnGuard.tsx b/src/ui/pages/Vpn/VpnGuard.tsx
index c49fb56..c02d8f6 100644
--- a/src/ui/pages/Vpn/VpnGuard.tsx
+++ b/src/ui/pages/Vpn/VpnGuard.tsx
@@ -47,7 +47,7 @@ const VpnGuard: React.FC<Props> = ({ children }) => {
             console.log("connectVPN result → ", res);
 
             // Only proceed if VPN actually connected
-            if (res === "Windows VPN connected silently") {
+            if (res === "Windows VPN connected silently" || res === "VPN already connected and healthy") {
 
                 const vpnRes = await window.electron.updateBaseURL(VPN_API);
                 console.log("vpnRes", vpnRes);