diff --git a/bun.lockb b/bun.lockb
new file mode 100755
index 0000000..d389625
Binary files /dev/null and b/bun.lockb differ
diff --git a/scripts/fetch-netbird-assets.mjs b/scripts/fetch-netbird-assets.mjs
index a047ad0..8d27f97 100644
--- a/scripts/fetch-netbird-assets.mjs
+++ b/scripts/fetch-netbird-assets.mjs
@@ -13,13 +13,13 @@ const targets = [
   {
     label: "macOS arm64",
     assetName: `netbird_${version}_darwin_arm64.tar.gz`,
-    outputDir: join(import.meta.dirname, "resources"),
+    outputDir: join(import.meta.dirname, "..", "resources"),
     files: [{ source: "netbird", destination: "netbird" }]
   },
   {
     label: "Windows amd64",
     assetName: `netbird_${version}_windows_amd64_signed.tar.gz`,
-    outputDir: join(import.meta.dirname, "resources"),
+    outputDir: join(import.meta.dirname, "..", "resources"),
     files: [
       { source: "netbird.exe", destination: "netbird.exe" },
       { source: "wintun.dll", destination: "wintun.dll" }
diff --git a/src/main.ts b/src/main.ts
index 98b9bfa..242b7e4 100644
--- a/src/main.ts
+++ b/src/main.ts
@@ -55,6 +55,7 @@ app.on('activate', () => {
 // In this file you can include the rest of your app's specific main process
 // code. You can also put them in separate files and import them here.
 let tray: Tray;
+let trayMenu: Menu;
 let window: BrowserWindow;
 let pollTimer: NodeJS.Timeout;
 let autoConnect = false;
@@ -103,7 +104,8 @@ function updateTray() {
     },
     { role: 'quit' }
   );
-  tray.setContextMenu(Menu.buildFromTemplate(template));
+  trayMenu = Menu.buildFromTemplate(template);
+  tray.setContextMenu(process.platform === 'darwin' ? null : trayMenu);
 }
 
 function setStatus(status: NetworkStatus) {
@@ -141,11 +143,11 @@ async function connect() {
 
   const client = netbirdClient();
   const serviceReady = await client.ensureService();
-  if (!serviceReady) {
+  if (!serviceReady.ok) {
     return setStatus({
       state: 'error',
       title: 'Connection failed',
-      message: `${GATEWAY_HOST} helper did not become ready.`
+      message: serviceReady.message || `${GATEWAY_HOST} helper did not become ready.`
     });
   }
 
@@ -225,11 +227,24 @@ function showWindow() {
   broadcastStatus();
 }
 
+function toggleWindow() {
+  if (window.isVisible()) {
+    window.hide();
+    return;
+  }
+
+  showWindow();
+}
+
 function createTray() {
   const icon = nativeImage.createFromPath(resourcePath('VynteIcon.png')).resize({ width: 18, height: 18 });
   tray = new Tray(icon);
   updateTray();
-  tray.on('click', showWindow);
+  tray.on('click', toggleWindow);
+  tray.on('right-click', () => {
+    window.hide();
+    tray.popUpContextMenu(trayMenu);
+  });
 }
 
 ipcMain.handle('status:get', () => withAutoConnect(cachedStatus));
@@ -243,4 +258,4 @@ ipcMain.handle('auto:toggle', () => {
   return autoConnect;
 });
 ipcMain.handle('app:quit', () => app.quit());
-ipcMain.handle('external:openGateway', () => shell.openExternal(MANAGEMENT_URL));
\ No newline at end of file
+ipcMain.handle('external:openGateway', () => shell.openExternal(MANAGEMENT_URL));
diff --git a/src/netbird.ts b/src/netbird.ts
index 98b0dbb..bef0c1a 100644
--- a/src/netbird.ts
+++ b/src/netbird.ts
@@ -9,6 +9,20 @@ export interface CommandResult {
   error: Error | null;
 }
 
+export interface ServiceReadyResult {
+  ok: boolean;
+  message?: string;
+}
+
+function commandDetails(label: string, result: CommandResult) {
+  const output = `${result.stdout}\n${result.stderr}\n${result.error?.message ?? ''}`.trim();
+  return output ? `${label}: ${output}` : `${label}: exited with code ${result.code ?? 1}`;
+}
+
+function shellQuote(value: string) {
+  return `'${value.replace(/'/g, "'\\''")}'`;
+}
+
 export class NetBirdClient {
   private executablePath: string;
 
@@ -30,8 +44,30 @@ export class NetBirdClient {
     });
   }
 
-  /// Deprecated???
-  runElevated(args: string[]): Promise<Omit<CommandResult, 'code'>> {
+  runElevated(args: string[]): Promise<CommandResult> {
+    if (process.platform === 'darwin') {
+      const command = [this.executablePath, ...args].map(shellQuote).join(' ');
+
+      return new Promise(resolve => {
+        execFile(
+          'osascript',
+          ['-e', `do shell script ${JSON.stringify(command)} with administrator privileges`],
+          {
+            timeout: 180000,
+          },
+          (error, stdout, stderr) => {
+            resolve({
+              ok: !error,
+              code: error && typeof (error as NodeJS.ErrnoException).code === 'number' ? (error as NodeJS.ErrnoException).code : 0,
+              stdout: stdout || '',
+              stderr: stderr || '',
+              error
+            });
+          }
+        )
+      });
+    }
+
     const quotedExe = this.executablePath.replace(/'/g, "''");
     const quotedArgs = args.map(arg => `'${String(arg).replace(/'/g, "''")}'`).join(',');
 
@@ -48,6 +84,7 @@ export class NetBirdClient {
         (error, stdout, stderr) => {
           resolve({
             ok: !error,
+            code: error && typeof (error as NodeJS.ErrnoException).code === 'number' ? (error as NodeJS.ErrnoException).code : 0,
             stdout: stdout || '',
             stderr: stderr || '',
             error
@@ -63,32 +100,82 @@ export class NetBirdClient {
     });
   }
 
-  async ensureService(): Promise<boolean> {
+  async ensureService(): Promise<ServiceReadyResult> {
     const status = await this.status({ timeout: 10000 });
 
-    if (status.ok) return true;
+    if (status.ok) return { ok: true };
 
-    await this.run([
-      'service',
-      'install',
+    const serviceArgs = [
       '--management-url',
       MANAGEMENT_URL,
       '--admin-url',
       MANAGEMENT_URL,
       '--log-level',
       'info'
+    ];
+
+    let install = await this.run([
+      'service',
+      'install',
+      ...serviceArgs
     ]);
 
-    await this.run(['service', 'start']);
+    let installDetails = commandDetails('service install', install);
+    let serviceAlreadyInstalled = installDetails.includes('Init already exists');
+    if (!install.ok && !serviceAlreadyInstalled && process.platform === 'darwin') {
+      install = await this.runElevated([
+        'service',
+        'install',
+        ...serviceArgs
+      ]);
+      installDetails = commandDetails('service install', install);
+      serviceAlreadyInstalled = installDetails.includes('Init already exists');
+    }
+
+    if (!install.ok && !serviceAlreadyInstalled) {
+      return {
+        ok: false,
+        message: installDetails
+      };
+    }
+
+    let reconfigureDetails = '';
+    if (serviceAlreadyInstalled) {
+      const reconfigure = await this.runElevated([
+        'service',
+        'reconfigure',
+        ...serviceArgs
+      ]);
+      if (!reconfigure.ok) {
+        reconfigureDetails = commandDetails('service reconfigure', reconfigure);
+      }
+    }
+
+    let start = await this.run(['service', 'start']);
+    if (!start.ok && process.platform === 'darwin') {
+      start = await this.runElevated(['service', 'start']);
+    }
+
+    const startDetails = commandDetails('service start', start);
+    let lastStatus = commandDetails('status', status);
 
     for (let index = 0; index < 20; index++) {
       const check = await this.status({ timeout: 8000 });
-      if (check.ok) return true;
+      if (check.ok) return { ok: true };
+      lastStatus = commandDetails('status', check);
 
       await new Promise<void>(resolve => setTimeout(resolve, 500));
     }
 
-    return false;
+    return {
+      ok: false,
+      message: [
+        serviceAlreadyInstalled ? installDetails : '',
+        reconfigureDetails,
+        start.ok ? '' : startDetails,
+        lastStatus
+      ].filter(Boolean).join('\n\n')
+    };
   }
 
   connect(): Promise<CommandResult> {
@@ -122,4 +209,4 @@ export class NetBirdClient {
       MANAGEMENT_URL
     ], { timeout: 60000 });
   }
-}
\ No newline at end of file
+}