diff --git a/workers/shared/workflow/destination_connector.py b/workers/shared/workflow/destination_connector.py
index 8d8ca3e25..05de89c27 100644
--- a/workers/shared/workflow/destination_connector.py
+++ b/workers/shared/workflow/destination_connector.py
@@ -461,6 +461,7 @@ def _check_and_handle_hitl(
             file_hash=file_ctx.file_hash,
             workflow=file_ctx.workflow,
             api_client=exec_ctx.api_client,
+            tool_execution_result=result.tool_execution_result,
             error=file_ctx.execution_error,
         )
 
@@ -1423,9 +1424,6 @@ def _should_handle_hitl(
                 f"{file_name}: Skipping HITL validation as we're not using file_history"
             )
             return False
-        if not file_hash.is_manualreview_required:
-            logger.info(f"{file_name}: File is not marked for manual review")
-            return False
 
         # Use class-level manual review service
         manual_review_service = self._ensure_manual_review_service(api_client)
@@ -1434,8 +1432,40 @@ def _should_handle_hitl(
             return False
 
         workflow_util = manual_review_service.get_workflow_util()
+
+        # Don't skip rule evaluation just because file wasn't pre-selected by percentage
+        # validate_db_rule will check both percentage selection AND rules with OR/AND logic
+        if not file_hash.is_manualreview_required:
+            logger.info(
+                f"{file_name}: File not pre-selected by percentage, "
+                f"but checking if rules match..."
+            )
+
+        # Wrap tool_execution_result in the expected structure for rule evaluation
+        # validate_db_rule expects: {"output": {...}, "metadata": {...}}
+        wrapped_result = None
+        if tool_execution_result:
+            if isinstance(tool_execution_result, dict):
+                # Check if tool_execution_result already has the correct structure
+                if "output" in tool_execution_result:
+                    # Already in correct format, use as-is
+                    wrapped_result = tool_execution_result
+                    logger.debug(
+                        f"{file_name}: tool_execution_result already has 'output' key, using as-is"
+                    )
+                else:
+                    # Wrap it in the expected structure
+                    wrapped_result = {"output": tool_execution_result, "metadata": {}}
+                    logger.debug(
+                        f"{file_name}: Wrapped tool_execution_result in output/metadata structure"
+                    )
+            else:
+                logger.warning(
+                    f"{file_name}: tool_execution_result is not a dict: {type(tool_execution_result)}"
+                )
+
         is_to_hitl = workflow_util.validate_db_rule(
-            tool_execution_result,
+            wrapped_result,
             workflow,
             file_hash.file_destination,
             file_hash.is_manualreview_required,