diff --git a/litellm/proxy/guardrails/guardrail_hooks/lakera_ai_v2.py b/litellm/proxy/guardrails/guardrail_hooks/lakera_ai_v2.py
index 7ef73a1f82f..1b3571cf242 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/lakera_ai_v2.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/lakera_ai_v2.py
@@ -117,7 +117,11 @@ def _pre_masking_scope_indices(
     Preserved in original order, so it lines up positionally with the
     ``messages_for_lakera`` list _build_lakera_inspection_messages/skip-filtering
     produces from the same input: both apply the identical "has text" and
-    "not skipped by role" predicates over the same original sequence."""
+    "not skipped by role" predicates over the same original sequence. Role
+    comparison is lowercased to match filter_messages_by_skip_flags's own
+    normalization (via its _message_role helper) -- an uppercase-cased
+    "System"/"TOOL" role must be excluded by both or the two lists disagree
+    on length and the caller's strict positional zip raises."""
     skip_system: Final = effective_skip_system_message_for_guardrail(guardrail)
     skip_tool: Final = effective_skip_tool_message_for_guardrail(guardrail)
     return tuple(
@@ -126,8 +130,8 @@ def _pre_masking_scope_indices(
         if isinstance(message, dict)
         and isinstance(message.get("content"), str)
         and message["content"]
-        and not (skip_system and message.get("role") == "system")
-        and not (skip_tool and message.get("role") == "tool")
+        and not (skip_system and str(message.get("role") or "").lower() == "system")
+        and not (skip_tool and str(message.get("role") or "").lower() == "tool")
     )
 
 
diff --git a/litellm/proxy/guardrails/init_guardrails.py b/litellm/proxy/guardrails/init_guardrails.py
index 9d23f1b3a8d..7926c9a6cfb 100644
--- a/litellm/proxy/guardrails/init_guardrails.py
+++ b/litellm/proxy/guardrails/init_guardrails.py
@@ -34,8 +34,8 @@ def init_guardrails_v2(
                 source="config",
             )
         except (ValueError, TypeError) as init_error:
-            verbose_proxy_logger.warning(
-                "Skipping guardrail '%s': invalid configuration: %s",
+            verbose_proxy_logger.error(
+                "Skipping guardrail '%s': invalid configuration, proxy is starting WITHOUT this guardrail: %s",
                 guardrail.get("guardrail_name"),
                 init_error,
             )
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_lakera_ai_v2.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_lakera_ai_v2.py
index d7725b5012e..0cc27ca169f 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_lakera_ai_v2.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_lakera_ai_v2.py
@@ -508,6 +508,33 @@ class TestPiiMaskingSafetyGuard:
         assert result["messages"][0] == SYSTEM_MSG
         assert "[MASKED" in result["messages"][1]["content"]
 
+    async def test_pii_only_violation_with_uppercase_skipped_role_masks_without_raising(self):
+        """
+        Greptile finding on BerriAI/litellm#34940: filter_messages_by_skip_flags
+        normalizes role casing (via _message_role's .lower()), but the scope-index
+        helper compared roles case-sensitively. A "System"-cased role survived the
+        scope-index filter while the shared filter correctly excluded it from what's
+        sent to Lakera, so scope_indices and the masked results came back different
+        lengths and the strict positional zip raised, turning a maskable PII-only
+        violation into an unhandled request failure instead of a masked response."""
+        guardrail = LakeraAIGuardrail(api_key="test_key", on_flagged="block", skip_system_message_in_guardrail=True)
+        uppercase_system_msg = {"role": "System", "content": "be nice"}
+        data = {
+            "messages": [uppercase_system_msg.copy(), USER_MSG.copy()],
+            "model": "gpt-3.5-turbo",
+            "metadata": {},
+        }
+        with patch.object(guardrail, "call_v2_guard", new_callable=AsyncMock) as mock_call:
+            mock_call.return_value = (PII_ONLY_LAKERA_RESPONSE, {})
+            result = await guardrail.async_pre_call_hook(
+                user_api_key_dict=UserAPIKeyAuth(api_key="test_key"),
+                cache=MagicMock(),
+                data=data,
+                call_type="completion",
+            )
+        assert result["messages"][0] == uppercase_system_msg
+        assert "[MASKED" in result["messages"][1]["content"]
+
     async def test_pii_only_violation_with_empty_text_message_masks_and_leaves_it_untouched(self):
         """build_inspection_messages drops empty-text messages before the skip filter
         ever sees them. The scope-index merge must leave that untouched empty message