diff --git a/src/webdrop_bridge/ui/main_window.py b/src/webdrop_bridge/ui/main_window.py
index 6c3b063..cfaeb54 100644
--- a/src/webdrop_bridge/ui/main_window.py
+++ b/src/webdrop_bridge/ui/main_window.py
@@ -522,15 +522,21 @@ class MainWindow(QMainWindow):
         
         asset_id = match.group(1)
         
-        # Check checkout status first
+        # Store callback ID for this check
+        callback_id = f"checkout_check_{id(self)}"
+        
+        # Check checkout status - use callback approach since Qt doesn't handle Promise returns well
         js_code = f"""
-        (async function() {{
+        (async () => {{
             try {{
                 const authToken = window.capturedAuthToken;
                 if (!authToken) {{
-                    return {{ error: 'No auth token' }};
+                    console.log('[Checkout Check] No auth token available');
+                    window['{callback_id}'] = JSON.stringify({{ error: 'No auth token' }});
+                    return;
                 }}
                 
+                console.log('[Checkout Check] Fetching asset data for {asset_id}');
                 const response = await fetch(
                     'https://devagravityprivate.azurewebsites.net/api/assets/{asset_id}?fields=checkout',
                     {{
@@ -542,37 +548,82 @@ class MainWindow(QMainWindow):
                     }}
                 );
                 
+                console.log('[Checkout Check] Response status:', response.status);
+                
                 if (response.ok) {{
                     const data = await response.json();
-                    return {{ checkout: data.checkout }};
+                    console.log('[Checkout Check] Full data:', JSON.stringify(data));
+                    console.log('[Checkout Check] Checkout field:', data.checkout);
+                    const hasCheckout = data.checkout && Object.keys(data.checkout).length > 0;
+                    console.log('[Checkout Check] Has checkout:', hasCheckout);
+                    window['{callback_id}'] = JSON.stringify({{ checkout: data.checkout, hasCheckout: hasCheckout }});
                 }} else {{
-                    return {{ error: 'Failed to fetch asset' }};
+                    console.log('[Checkout Check] Failed to fetch, status:', response.status);
+                    window['{callback_id}'] = JSON.stringify({{ error: 'Failed to fetch asset', status: response.status }});
                 }}
             }} catch (error) {{
-                return {{ error: error.toString() }};
+                console.error('[Checkout Check] Error:', error);
+                window['{callback_id}'] = JSON.stringify({{ error: error.toString() }});
             }}
         }})();
         """
         
-        def on_checkout_status(result):
-            """Callback when checkout status is received."""
-            if not result or isinstance(result, dict) and result.get('error'):
-                logger.warning(f"Could not check checkout status: {result}")
-                # Show dialog anyway as fallback
-                self._show_checkout_dialog(azure_url, filename)
-                return
-            
-            # Check if already checked out
-            checkout_info = result.get('checkout')
-            if checkout_info:
-                logger.info(f"Asset {filename} is already checked out, skipping dialog")
-                return
-            
-            # Not checked out, show confirmation dialog
-            self._show_checkout_dialog(azure_url, filename)
+        # Execute the async fetch
+        self.web_view.page().runJavaScript(js_code)
         
-        # Execute JavaScript to check status
-        self.web_view.page().runJavaScript(js_code, on_checkout_status)
+        # After a short delay, read the result from window variable
+        def check_result():
+            read_code = f"window['{callback_id}']"
+            self.web_view.page().runJavaScript(read_code, lambda result: self._handle_checkout_status(result, azure_url, filename, callback_id))
+        
+        # Wait 500ms for async fetch to complete
+        from PySide6.QtCore import QTimer
+        QTimer.singleShot(500, check_result)
+    
+    def _handle_checkout_status(self, result, azure_url: str, filename: str, callback_id: str) -> None:
+        """Handle the result of checkout status check.
+        
+        Args:
+            result: Result from JavaScript (JSON string)
+            azure_url: Azure URL
+            filename: Asset filename
+            callback_id: Callback ID to clean up
+        """
+        # Clean up window variable
+        cleanup_code = f"delete window['{callback_id}']"
+        self.web_view.page().runJavaScript(cleanup_code)
+        
+        logger.debug(f"Checkout status result type: {type(result)}, value: {result}")
+        
+        if not result or not isinstance(result, str):
+            logger.warning(f"Checkout status check returned invalid result: {result}")
+            self._show_checkout_dialog(azure_url, filename)
+            return
+        
+        # Parse JSON string
+        try:
+            import json
+            parsed_result = json.loads(result)
+        except (json.JSONDecodeError, ValueError) as e:
+            logger.warning(f"Failed to parse checkout status result: {e}")
+            self._show_checkout_dialog(azure_url, filename)
+            return
+        
+        if parsed_result.get('error'):
+            logger.warning(f"Could not check checkout status: {parsed_result}")
+            self._show_checkout_dialog(azure_url, filename)
+            return
+        
+        # Check if already checked out
+        has_checkout = parsed_result.get('hasCheckout', False)
+        if has_checkout:
+            checkout_info = parsed_result.get('checkout', {})
+            logger.info(f"Asset {filename} is already checked out: {checkout_info}, skipping dialog")
+            return
+        
+        # Not checked out, show confirmation dialog
+        logger.debug(f"Asset {filename} is not checked out, showing dialog")
+        self._show_checkout_dialog(azure_url, filename)
     
     def _show_checkout_dialog(self, azure_url: str, filename: str) -> None:
         """Show the checkout confirmation dialog.