diff --git a/litellm/llms/anthropic/chat/guardrail_translation/handler.py b/litellm/llms/anthropic/chat/guardrail_translation/handler.py
index 9f3c85b555a..b222548f4ec 100644
--- a/litellm/llms/anthropic/chat/guardrail_translation/handler.py
+++ b/litellm/llms/anthropic/chat/guardrail_translation/handler.py
@@ -234,19 +234,20 @@ def _write_back_message_text(message: _WritableMessage, target: MessageTextTarge
 _TOOL_USE_INPUT_ADAPTER: Final = TypeAdapter(dict[str, object])
 
 
-def _write_back_tool_use(message: _WritableMessage, target: ToolUseInputTarget, shape: _ToolCallShape) -> None:
+def _rewritten_tool_use_input(arguments: str) -> Mapping[str, object] | None:
+    try:
+        return _TOOL_USE_INPUT_ADAPTER.validate_json(arguments)
+    except ValidationError:
+        return None
+
+
+def _write_back_tool_use(
+    message: _WritableMessage, target: ToolUseInputTarget, shape: _ToolCallShape, rewritten_input: Mapping[str, object]
+) -> None:
     content: Final = message.get("content", None)
     block: Final = content[target.content_idx] if isinstance(content, list) else None
     if not isinstance(block, dict):
         return
-    try:
-        rewritten_input: Final = _TOOL_USE_INPUT_ADAPTER.validate_json(shape.arguments)
-    except ValidationError:
-        verbose_proxy_logger.warning(
-            "Anthropic Messages: guardrail returned arguments that are not a JSON object for tool_use %s; keeping its input",
-            block.get("id"),
-        )
-        return
     block["input"] = rewritten_input  # mutable-ok: guardrails rewrite the caller's request payload in place
     if shape.name is not None and shape.name != block.get("name"):
         block["name"] = shape.name  # mutable-ok: guardrails rewrite the caller's request payload in place
@@ -688,6 +689,7 @@ class AnthropicMessagesHandler(BaseTranslation):
                     scanned_tool_calls=scanned_tool_calls,
                     pre_guardrail_tool_calls=pre_guardrail_tool_calls,
                     returned_tool_calls=guardrailed_inputs.get("tool_calls"),
+                    guardrail_name=guardrail_to_apply.guardrail_name,
                 )
 
         verbose_proxy_logger.debug("Anthropic Messages: Processed input messages: %s", messages)
@@ -1116,15 +1118,25 @@ class AnthropicMessagesHandler(BaseTranslation):
         scanned_tool_calls: tuple[ScannedToolCall, ...],
         pre_guardrail_tool_calls: tuple[_ToolCallShape, ...],
         returned_tool_calls: Sequence[object] | None,
+        guardrail_name: str | None,
     ) -> None:
         post_guardrail_tool_calls: Final = _tool_call_shapes(
             returned_tool_calls
             if returned_tool_calls is not None and len(returned_tool_calls) == len(pre_guardrail_tool_calls)
             else tuple(item.tool_call for item in scanned_tool_calls)
         )
-        for item, before, after in zip(scanned_tool_calls, pre_guardrail_tool_calls, post_guardrail_tool_calls):
-            if before != after:
-                _write_back_tool_use(messages[item.target.msg_idx], item.target, after)
+        rewritten: Final = tuple(
+            (item, after, _rewritten_tool_use_input(after.arguments))
+            for item, before, after in zip(scanned_tool_calls, pre_guardrail_tool_calls, post_guardrail_tool_calls)
+            if before != after
+        )
+        applicable: Final = tuple(
+            (item, after, rewritten_input) for item, after, rewritten_input in rewritten if rewritten_input is not None
+        )
+        if len(applicable) != len(rewritten):
+            raise unappliable_request_rewrite(guardrail_name)
+        for item, after, rewritten_input in applicable:
+            _write_back_tool_use(messages[item.target.msg_idx], item.target, after, rewritten_input)
 
     async def process_output_response(
         self,
diff --git a/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py b/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
index 287674afaa7..b73ef6453fa 100644
--- a/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
+++ b/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
@@ -2328,16 +2328,20 @@ class TestAnthropicMessagesTopLevelSystemAndToolUseInputs:
         assert data["messages"][2]["content"][0]["tool_use_id"] == "toolu_01"
 
     @pytest.mark.asyncio
-    async def test_non_json_rewritten_arguments_keep_the_tool_use_input(self):
+    async def test_non_json_rewritten_arguments_are_rejected_by_name(self):
+        from litellm.llms.base_llm.guardrail_translation.utils import UnappliableRequestRewrite
+
         handler = AnthropicMessagesHandler()
         guardrail = ToolCallArgumentsMaskingGuardrail(replacement_arguments="[REDACTED]")
         data = self._tool_use_conversation(system="You are a careful agent harness.")
+        original = json.loads(json.dumps(data))
 
-        await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
+        with pytest.raises(UnappliableRequestRewrite) as excinfo:
+            await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
 
-        assert data["messages"][1]["content"][0]["input"] == {
-            "cmd": "AWS_ACCESS_KEY_ID=POISON aws sts get-caller-identity"
-        }
+        assert excinfo.value.guardrail_name == "scan-only-capture"
+        assert data["system"] == original["system"], "a rejected rewrite must leave the request untouched"
+        assert data["messages"] == original["messages"], "a rejected rewrite must leave the request untouched"
 
     @pytest.mark.asyncio
     async def test_scan_only_tool_results_keeps_system_and_tool_use_out(self):