diff --git a/enterprise/litellm_enterprise/enterprise_callbacks/secret_detection.py b/enterprise/litellm_enterprise/enterprise_callbacks/secret_detection.py
index 88c48ea0b8d..40f25f6b36d 100644
--- a/enterprise/litellm_enterprise/enterprise_callbacks/secret_detection.py
+++ b/enterprise/litellm_enterprise/enterprise_callbacks/secret_detection.py
@@ -454,6 +454,8 @@ _CONFIG_SECTION: Final = "litellm-prompt"
 
 _JSON_STRING: Final = TypeAdapter(str)
 
+_KEY_CONTEXT: Final = 64
+
 _ASSIGNMENT_LINE: Final = re.compile(r"[^\s\[#;:=][^:=]*[:=]")
 
 _SHELL_ASSIGNMENT: Final = re.compile(r"(?P<key>[^\s\[#;:=](?:[^:=]*[^\s:=])?)=(?P<value>\S+)")
@@ -546,7 +548,7 @@ def _json_unescaped(value: str) -> str:
 
 def _json_line(key: str | None, text: str) -> str:
     value: Final = json.dumps(text, ensure_ascii=False)
-    return value if key is None else f"{json.dumps(key, ensure_ascii=False)}: {value}"
+    return value if key is None else f"{json.dumps(key[-_KEY_CONTEXT:], ensure_ascii=False)}: {value}"
 
 
 def _value_in_texts(value: str, texts: Sequence[str]) -> str | None:
diff --git a/litellm/proxy/guardrails/_content_utils.py b/litellm/proxy/guardrails/_content_utils.py
index b095c853ebe..c352545ab81 100644
--- a/litellm/proxy/guardrails/_content_utils.py
+++ b/litellm/proxy/guardrails/_content_utils.py
@@ -98,12 +98,12 @@ def _tool_arguments(arguments: str) -> JsonValue:
             parse_constant=_finite_number,
         )
     )
-    json.dumps(parsed, ensure_ascii=False).encode("utf-8")
+    json.dumps(parsed, ensure_ascii=False).encode("utf-8")  # raises for lone surrogates, which stay raw text
     return parsed
 
 
 def iter_tool_json_fields(value: object) -> Iterator[tuple[str | None, str]]:
-    """Yield ``(key, text)`` for every non-empty string leaf; the key is None for list items and a bare root."""
+    """Yield ``(nearest key, text)`` for every non-empty string leaf; list items take their parent's key."""
     pending: Final[list[tuple[object, str | None]]] = [(value, None)]  # mutable-ok: owned DFS stack avoids recursion
     while pending:
         current, key = pending.pop()
@@ -120,7 +120,7 @@ def iter_tool_json_fields(value: object) -> Iterator[tuple[str | None, str]]:
         items = _object_list(current)
         if items is None:
             raise ValueError("Invalid tool JSON payload")
-        pending.extend((child, None) for child in reversed(items))
+        pending.extend((child, key) for child in reversed(items))
 
 
 def iter_tool_json_text(value: object) -> Iterator[str]:
diff --git a/tests/integration/security/test_tool_text_guardrail_consumers.py b/tests/integration/security/test_tool_text_guardrail_consumers.py
index b4d7ff79385..4a5c8afbbb1 100644
--- a/tests/integration/security/test_tool_text_guardrail_consumers.py
+++ b/tests/integration/security/test_tool_text_guardrail_consumers.py
@@ -214,6 +214,8 @@ def test_read_only_vendors_receive_tool_and_system_text(
 
 
 def test_moderation_flag_in_tool_result_blocks(rig: Rig) -> None:
+    rig.wire.drain()
     response: Final = rig.proxy.request("POST", "/v1/messages", _messages(FLAGGED))
     assert response.status_code == 403, response.text
     assert "Violated content safety policy" in response.text
+    assert _provider_calls(rig.wire.drain()) == ()
diff --git a/tests/unit/enterprise/enterprise_callbacks/test_secret_detection.py b/tests/unit/enterprise/enterprise_callbacks/test_secret_detection.py
index 7cb38f214db..f398046f602 100644
--- a/tests/unit/enterprise/enterprise_callbacks/test_secret_detection.py
+++ b/tests/unit/enterprise/enterprise_callbacks/test_secret_detection.py
@@ -147,6 +147,18 @@ async def test_pre_call_hook_records_secrets_found_only_in_tool_payloads():
     assert recorded["masked_entity_count"] == {"AWS Access Key": 1}
 
 
+@pytest.mark.parametrize(
+    ("payload", "expected"),
+    (
+        ({"password": ["hunter2brahms9x", "safe"]}, {"password": ["[REDACTED]", "safe"]}),
+        (["a8f5f167f44f4964e6c998dee827110c", "safe"], ["[REDACTED]", "safe"]),
+    ),
+    ids=("credential-key-over-list", "unkeyed-high-entropy"),
+)
+def test_list_items_are_scanned_beside_their_parent_key_or_quoted(payload, expected):
+    assert _guardrail().redact_tool_payload(payload) == expected
+
+
 def test_long_key_over_a_list_is_scanned_in_bounded_time():
     payload = {"k" * 10_000: ["v"] * 1000 + [f"AWS_ACCESS_KEY_ID={AWS_KEY}"]}
     started = time.perf_counter()