diff --git a/mac/.gitignore b/mac/.gitignore
index 69d030ab..23cfc637 100644
--- a/mac/.gitignore
+++ b/mac/.gitignore
@@ -33,6 +33,9 @@ VibeTunnel/Local.xcconfig
 # Build output
 build_output.txt
 
+# Release state - temporary file
+.release-state.json
+
 # Sparkle private key - NEVER commit this!
 sparkle-private-ed-key.pem
 sparkle-private-key-KEEP-SECURE.txt
diff --git a/web/src/client/components/session-view.ts b/web/src/client/components/session-view.ts
index 4cce2227..014b1a02 100644
--- a/web/src/client/components/session-view.ts
+++ b/web/src/client/components/session-view.ts
@@ -93,6 +93,7 @@ export class SessionView extends LitElement {
   @state() private terminalTheme: TerminalThemeId = 'auto';
   @state() private terminalContainerHeight = '100%';
   @state() private isLandscape = false;
+  @state() private macAppConnected = false;
 
   private preferencesManager = TerminalPreferencesManager.getInstance();
 
@@ -199,6 +200,9 @@ export class SessionView extends LitElement {
     super.connectedCallback();
     this.connected = true;
 
+    // Check server status to see if Mac app is connected
+    this.checkServerStatus();
+
     // Check initial orientation
     this.checkOrientation();
 
@@ -611,6 +615,11 @@ export class SessionView extends LitElement {
   }
 
   private handleScreenshare() {
+    // Only allow screenshare if Mac app is connected
+    if (!this.macAppConnected) {
+      logger.warn('Screenshare requested but Mac app is not connected');
+      return;
+    }
     // Dispatch event to start screenshare
     this.dispatchEvent(
       new CustomEvent('start-screenshare', {
@@ -620,6 +629,23 @@ export class SessionView extends LitElement {
     );
   }
 
+  private async checkServerStatus() {
+    try {
+      const response = await fetch('/api/server/status', {
+        headers: authClient.getAuthHeader(),
+      });
+      if (response.ok) {
+        const status = await response.json();
+        this.macAppConnected = status.macAppConnected || false;
+        logger.debug('server status:', status);
+      }
+    } catch (error) {
+      logger.warn('failed to check server status:', error);
+      // Default to not connected if we can't check
+      this.macAppConnected = false;
+    }
+  }
+
   private handleOpenSettings() {
     // Dispatch event to open settings modal
     this.dispatchEvent(
@@ -1293,6 +1319,7 @@ export class SessionView extends LitElement {
           .onFontSizeChange=${(size: number) => this.handleFontSizeChange(size)}
           .onScreenshare=${() => this.handleScreenshare()}
           .onOpenSettings=${() => this.handleOpenSettings()}
+          .macAppConnected=${this.macAppConnected}
           @close-width-selector=${() => {
             this.showWidthSelector = false;
             this.customWidth = '';
diff --git a/web/src/client/components/session-view/mobile-menu.ts b/web/src/client/components/session-view/mobile-menu.ts
index bf7bb4e0..d19f8058 100644
--- a/web/src/client/components/session-view/mobile-menu.ts
+++ b/web/src/client/components/session-view/mobile-menu.ts
@@ -26,6 +26,7 @@ export class MobileMenu extends LitElement {
   @property({ type: Function }) onMaxWidthToggle?: () => void;
   @property({ type: Function }) onOpenSettings?: () => void;
   @property({ type: String }) currentTheme: Theme = 'system';
+  @property({ type: Boolean }) macAppConnected = false;
 
   @state() private showMenu = false;
   @state() private focusedIndex = -1;
@@ -225,6 +226,7 @@ export class MobileMenu extends LitElement {
   }
 
   private renderDropdown() {
+    let menuItemIndex = 0;
     return html`
       <div 
         class="absolute right-0 top-full mt-2 bg-surface border border-base rounded-lg shadow-xl py-1 min-w-[200px]"
@@ -233,7 +235,7 @@ export class MobileMenu extends LitElement {
         
         <!-- New Session -->
         <button
-          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === 0 ? 'bg-secondary text-primary' : ''}"
+          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === menuItemIndex++ ? 'bg-secondary text-primary' : ''}"
           @click=${() => this.handleAction(this.onCreateSession)}
           data-testid="mobile-new-session"
           tabindex="${this.showMenu ? '0' : '-1'}"
@@ -248,7 +250,7 @@ export class MobileMenu extends LitElement {
         
         <!-- File Browser -->
         <button
-          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === 1 ? 'bg-secondary text-primary' : ''}"
+          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === menuItemIndex++ ? 'bg-secondary text-primary' : ''}"
           @click=${() => this.handleAction(this.onOpenFileBrowser)}
           data-testid="mobile-file-browser"
           tabindex="${this.showMenu ? '0' : '-1'}"
@@ -259,25 +261,31 @@ export class MobileMenu extends LitElement {
           Browse Files
         </button>
         
-        <!-- Screenshare -->
-        <button
-          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === 2 ? 'bg-secondary text-primary' : ''}"
-          @click=${() => this.handleAction(this.onScreenshare)}
-          data-testid="mobile-screenshare"
-          tabindex="${this.showMenu ? '0' : '-1'}"
-        >
-          <svg width="16" height="16" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2">
-            <rect x="2" y="3" width="20" height="14" rx="2"/>
-            <line x1="8" y1="21" x2="16" y2="21"/>
-            <line x1="12" y1="17" x2="12" y2="21"/>
-            <circle cx="12" cy="10" r="3" fill="currentColor" stroke="none"/>
-          </svg>
-          Screenshare
-        </button>
+        <!-- Screenshare - only show if Mac app is connected -->
+        ${
+          this.macAppConnected
+            ? html`
+              <button
+                class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === menuItemIndex++ ? 'bg-secondary text-primary' : ''}"
+                @click=${() => this.handleAction(this.onScreenshare)}
+                data-testid="mobile-screenshare"
+                tabindex="${this.showMenu ? '0' : '-1'}"
+              >
+                <svg width="16" height="16" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2">
+                  <rect x="2" y="3" width="20" height="14" rx="2"/>
+                  <line x1="8" y1="21" x2="16" y2="21"/>
+                  <line x1="12" y1="17" x2="12" y2="21"/>
+                  <circle cx="12" cy="10" r="3" fill="currentColor" stroke="none"/>
+                </svg>
+                Screenshare
+              </button>
+            `
+            : ''
+        }
         
         <!-- Width Settings -->
         <button
-          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === 3 ? 'bg-secondary text-primary' : ''}"
+          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === menuItemIndex++ ? 'bg-secondary text-primary' : ''}"
           @click=${() => this.handleAction(this.onMaxWidthToggle)}
           data-testid="mobile-width-settings"
           tabindex="${this.showMenu ? '0' : '-1'}"
@@ -290,7 +298,7 @@ export class MobileMenu extends LitElement {
         
         <!-- Theme Toggle -->
         <button
-          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === 4 ? 'bg-secondary text-primary' : ''}"
+          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === menuItemIndex++ ? 'bg-secondary text-primary' : ''}"
           @click=${() => this.handleThemeChange()}
           data-testid="mobile-theme-toggle"
           tabindex="${this.showMenu ? '0' : '-1'}"
@@ -301,7 +309,7 @@ export class MobileMenu extends LitElement {
         
         <!-- Settings -->
         <button
-          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === 5 ? 'bg-secondary text-primary' : ''}"
+          class="w-full text-left px-4 py-3 text-sm font-mono text-primary hover:bg-secondary hover:text-primary flex items-center gap-3 ${this.focusedIndex === menuItemIndex++ ? 'bg-secondary text-primary' : ''}"
           @click=${() => this.handleAction(this.onOpenSettings)}
           data-testid="mobile-settings"
           tabindex="${this.showMenu ? '0' : '-1'}"
diff --git a/web/src/client/components/session-view/session-header.ts b/web/src/client/components/session-view/session-header.ts
index ec5271f1..65f4ac02 100644
--- a/web/src/client/components/session-view/session-header.ts
+++ b/web/src/client/components/session-view/session-header.ts
@@ -50,6 +50,7 @@ export class SessionHeader extends LitElement {
   @property({ type: String }) currentTheme = 'system';
   @property({ type: Boolean }) keyboardCaptureActive = true;
   @property({ type: Boolean }) isMobile = false;
+  @property({ type: Boolean }) macAppConnected = false;
   @state() private isHovered = false;
 
   connectedCallback() {
@@ -262,18 +263,24 @@ export class SessionHeader extends LitElement {
                 />
               </svg>
             </button>
-            <button
-              class="bg-bg-tertiary border border-border rounded-lg p-2 font-mono text-muted transition-all duration-200 hover:text-primary hover:bg-surface-hover hover:border-primary hover:shadow-sm flex-shrink-0"
-              @click=${() => this.onScreenshare?.()}
-              title="Start Screenshare"
-            >
-              <svg width="16" height="16" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2">
-                <rect x="2" y="3" width="20" height="14" rx="2"/>
-                <line x1="8" y1="21" x2="16" y2="21"/>
-                <line x1="12" y1="17" x2="12" y2="21"/>
-                <circle cx="12" cy="10" r="3" fill="currentColor" stroke="none"/>
-              </svg>
-            </button>
+            ${
+              this.macAppConnected
+                ? html`
+                  <button
+                    class="bg-bg-tertiary border border-border rounded-lg p-2 font-mono text-muted transition-all duration-200 hover:text-primary hover:bg-surface-hover hover:border-primary hover:shadow-sm flex-shrink-0"
+                    @click=${() => this.onScreenshare?.()}
+                    title="Start Screenshare"
+                  >
+                    <svg width="16" height="16" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2">
+                      <rect x="2" y="3" width="20" height="14" rx="2"/>
+                      <line x1="8" y1="21" x2="16" y2="21"/>
+                      <line x1="12" y1="17" x2="12" y2="21"/>
+                      <circle cx="12" cy="10" r="3" fill="currentColor" stroke="none"/>
+                    </svg>
+                  </button>
+                `
+                : ''
+            }
             <button
               class="bg-bg-tertiary border border-border rounded-lg px-3 py-2 font-mono text-xs text-muted transition-all duration-200 hover:text-primary hover:bg-surface-hover hover:border-primary hover:shadow-sm flex-shrink-0 width-selector-button"
               @click=${() => this.onMaxWidthToggle?.()}
@@ -295,6 +302,7 @@ export class SessionHeader extends LitElement {
               .onOpenSettings=${this.onOpenSettings}
               .onCreateSession=${this.onCreateSession}
               .currentTheme=${this.currentTheme}
+              .macAppConnected=${this.macAppConnected}
             ></mobile-menu>
           </div>