diff --git a/features/conversation-assistant/macos/install.sh b/features/conversation-assistant/macos/install.sh
index c6b11ba71..b7e591b3d 100755
--- a/features/conversation-assistant/macos/install.sh
+++ b/features/conversation-assistant/macos/install.sh
@@ -238,21 +238,42 @@ show_permissions_guide() {
     echo "The Conversation Assistant requires Full Disk Access to read the iMessage database."
     echo ""
     echo "To grant access:"
-    echo "  1. Open System Settings → Privacy & Security → Full Disk Access"
+    echo "  1. System Settings will open to Full Disk Access"
     echo "  2. Click the '+' button"
     echo "  3. Navigate to: $INSTALL_DIR/$APP_NAME.app"
     echo "  4. Select the app and click 'Open'"
     echo "  5. Enable the toggle next to $APP_NAME"
     echo ""
 
-    read -p "Press Enter to open System Settings, or 'n' to skip: " open_settings
-
-    if [[ "$open_settings" != "n" && "$open_settings" != "N" ]]; then
-        # Open System Settings to the correct pane (macOS Ventura+)
-        open "x-apple.systempreferences:com.apple.preference.security?Privacy_AllFiles"
+    # Check if running interactively (has a TTY)
+    if [[ -t 0 ]]; then
+        read -p "Press Enter to open System Settings, or 'n' to skip: " open_settings
+        if [[ "$open_settings" != "n" && "$open_settings" != "N" ]]; then
+            open_fda_settings
+        fi
+    else
+        # Non-interactive mode (SSH batch) - auto-open settings
+        print_info "Opening System Settings → Full Disk Access..."
+        open_fda_settings
     fi
 }
 
+open_fda_settings() {
+    # Open System Settings to Full Disk Access pane (macOS Ventura+)
+    # Use osascript to ensure it opens in the user's GUI session (works via SSH)
+    osascript -e 'tell application "System Settings"
+        activate
+        delay 0.5
+        tell application "System Events"
+            keystroke "Full Disk Access"
+            delay 0.3
+            key code 36
+        end tell
+    end tell' 2>/dev/null || \
+    open "x-apple.systempreferences:com.apple.preference.security?Privacy_AllFiles" 2>/dev/null || \
+    open "/System/Applications/System Settings.app" 2>/dev/null
+}
+
 register_device() {
     print_step "Starting the agent for device registration..."