debug: Add comprehensive logging to trace error handling flow

- Add detailed logging to API key validation function
- Add debug logs to frontend error parsing
- Add debug logs to TanStack Query error handler
- This will help identify where error handling is failing in the UI

archon-ui-main/src/features/knowledge/hooks/useKnowledgeQueries.ts

@@ -260,6 +260,11 @@ export function useCrawlUrl() {
       return response;
     },
     onError: (error, _variables, context) => {
+      console.log(`🔍 [Crawl Hook] Received error:`, error);
+      console.log(`🔍 [Crawl Hook] Error type: ${typeof error}`);
+      console.log(`🔍 [Crawl Hook] Error keys:`, Object.keys(error || {}));
+      console.log(`🔍 [Crawl Hook] Is OpenAI error:`, (error as EnhancedError)?.isOpenAIError);
+      
       // Rollback optimistic updates on error
       if (context?.previousKnowledge) {
         queryClient.setQueryData(knowledgeKeys.lists(), context.previousKnowledge);
@@ -278,6 +283,8 @@ export function useCrawlUrl() {
       const errorMessage = (error as EnhancedError)?.isOpenAIError 
         ? getDisplayErrorMessage(error as EnhancedError)
         : (error instanceof Error ? error.message : "Failed to start crawl");
+      
+      console.log(`🔍 [Crawl Hook] Final error message for toast:`, errorMessage);
       showToast(errorMessage, "error");
     },
   });

archon-ui-main/src/features/knowledge/services/apiWithEnhancedErrors.ts

@@ -18,6 +18,10 @@ export async function callKnowledgeAPI<T>(
     // Use the ETag-aware API client for caching benefits
     return await callAPIWithETag<T>(endpoint, options);
   } catch (error: any) {
+    console.log(`🔍 [Knowledge API] Caught error for ${endpoint}:`, error);
+    console.log(`🔍 [Knowledge API] Error type: ${typeof error}`);
+    console.log(`🔍 [Knowledge API] Error keys:`, Object.keys(error || {}));
+    
     // Apply enhanced error parsing for OpenAI errors
     const enhancedError = parseKnowledgeBaseError({
       status: error.statusCode || error.status,
@@ -25,12 +29,17 @@ export async function callKnowledgeAPI<T>(
       detail: error.detail
     });
     
+    console.log(`🔍 [Knowledge API] Enhanced error:`, enhancedError);
+    console.log(`🔍 [Knowledge API] Is OpenAI error:`, enhancedError.isOpenAIError);
+    console.log(`🔍 [Knowledge API] Error details:`, enhancedError.errorDetails);
+    
     // Preserve the original error structure but enhance with our parsing
     const finalError = error as EnhancedError;
     finalError.isOpenAIError = enhancedError.isOpenAIError;
     finalError.errorDetails = enhancedError.errorDetails;
     finalError.message = enhancedError.message;
     
+    console.log(`🔍 [Knowledge API] Final error to throw:`, finalError);
     throw finalError;
   }
 }

python/src/server/api_routes/knowledge_api.py

@@ -100,21 +100,24 @@ async def _validate_openai_api_key() -> None:
     Raises:
         HTTPException: 401 if API key is invalid/missing, 429 if quota exhausted
     """
+    # Import embedding exceptions for specific error handling
+    from ..services.embeddings.embedding_exceptions import (
+        EmbeddingAuthenticationError,
+        EmbeddingQuotaExhaustedError,
+    )
+    
     try:
         # Test the API key with a minimal embedding request
         from ..services.embeddings.embedding_service import create_embedding
 
+        logger.info("🔑 Validating OpenAI API key before starting operation...")
         # Try to create a test embedding with minimal content
-        await create_embedding(text="test")
+        test_result = await create_embedding(text="test")
-
+        
-    except Exception as e:
+        if test_result:
-        # Import embedding exceptions for specific error handling
+            logger.info("✅ OpenAI API key validation successful")
-        from ..services.embeddings.embedding_exceptions import (
+        else:
-            EmbeddingAuthenticationError,
+            logger.error("❌ OpenAI API key validation failed - no embedding returned")
-            EmbeddingQuotaExhaustedError,
-        )
-
-        if isinstance(e, EmbeddingAuthenticationError):
             raise HTTPException(
                 status_code=401,
                 detail={
@@ -123,20 +126,35 @@ async def _validate_openai_api_key() -> None:
                     "error_type": "authentication_failed"
                 }
             )
-        elif isinstance(e, EmbeddingQuotaExhaustedError):
+
-            raise HTTPException(
+    except EmbeddingAuthenticationError as e:
-                status_code=429,
+        logger.error(f"❌ OpenAI authentication failed: {e}")
-                detail={
+        raise HTTPException(
-                    "error": "OpenAI quota exhausted",
+            status_code=401,
-                    "message": "Your OpenAI API key has no remaining credits. Please add credits to your account.",
+            detail={
-                    "error_type": "quota_exhausted"
+                "error": "Invalid OpenAI API key",
-                }
+                "message": "Please verify your OpenAI API key in Settings before starting a crawl.",
-            )
+                "error_type": "authentication_failed",
-        else:
+                "api_key_prefix": getattr(e, "api_key_prefix", None),
-            # For any other errors, allow the operation to continue
+            }
-            # The error will be caught later during actual processing
+        ) from None
-            logger.warning(f"API key validation failed with unexpected error: {e}")
+    except EmbeddingQuotaExhaustedError as e:
-            pass
+        logger.error(f"❌ OpenAI quota exhausted: {e}")
+        raise HTTPException(
+            status_code=429,
+            detail={
+                "error": "OpenAI quota exhausted",
+                "message": "Your OpenAI API key has no remaining credits. Please add credits to your account.",
+                "error_type": "quota_exhausted",
+                "tokens_used": getattr(e, "tokens_used", None),
+            }
+        ) from None
+    except Exception as e:
+        # For any other errors, log them but allow the operation to continue
+        # The error will be caught later during actual processing
+        logger.warning(f"⚠️ API key validation failed with unexpected error: {e}")
+        # Don't block the operation for unexpected validation errors
+        pass
 
 
 # Request Models