diff --git a/litellm/_logging.py b/litellm/_logging.py
index bcf77d65d96..706ae0c8282 100644
--- a/litellm/_logging.py
+++ b/litellm/_logging.py
@@ -13,6 +13,7 @@ from urllib.parse import unquote
 
 import litellm
 from litellm.constants import (
+    DEFAULT_MAX_RECURSE_DEPTH,
     LITELLM_TRUNCATED_PAYLOAD_FIELD,
     LITELLM_TRUNCATION_STDOUT_SAFEGUARD_NOTE,
     MAX_BASE64_LENGTH_STDOUT_LOG,
@@ -88,11 +89,25 @@ def _is_redacted(record: logging.LogRecord) -> bool:
     return getattr(record, _REDACTED_RECORD_ATTR, False) is True
 
 
+def _is_secret_free(key: str | None, value: object, depth: int) -> bool:
+    if depth > DEFAULT_MAX_RECURSE_DEPTH:
+        return False
+    if isinstance(value, str):
+        return _redact_structured_value(key, value) == value
+    if isinstance(value, _UNREDACTED_SCALAR_TYPES):
+        return True
+    if isinstance(value, dict):
+        return all(isinstance(k, str) and _is_secret_free(k, v, depth + 1) for k, v in value.items())
+    if isinstance(value, (list, tuple)):
+        return all(_is_secret_free(key, item, depth + 1) for item in value)
+    return False
+
+
 def _redact_extra_value(key: str, value: object) -> object:
+    if _is_secret_free(key, value, 1):
+        return value
     try:
-        rendered: Final = safe_dumps({key: value})
-        scrubbed: Final = safe_dumps({key: value}, value_transform=_redact_structured_value)
-        return value if scrubbed == rendered else json.loads(scrubbed)[key]
+        return json.loads(safe_dumps({key: value}, value_transform=_redact_structured_value))[key]
     except (TypeError, ValueError, KeyError):
         return _redact_string(str(value))
 
diff --git a/tests/test_litellm/test_logging.py b/tests/test_litellm/test_logging.py
index 43be8701b49..884c120f5c9 100644
--- a/tests/test_litellm/test_logging.py
+++ b/tests/test_litellm/test_logging.py
@@ -1029,17 +1029,23 @@ def test_unserializable_extra_never_breaks_the_filter(monkeypatch, extra):
 class _RequestExtra:
     model: str
     attempt: int
+    api_key: str = dataclasses.field(default="", repr=False)
+
+
+def _nest(value: object, levels: int) -> object:
+    return value if levels == 0 else _nest([value], levels - 1)
 
 
 @pytest.mark.parametrize(
     "extra",
     (
         ("gpt-4o", 2),
-        {"gpt-4o", "gpt-4o-mini"},
-        {"models": ("gpt-4o", "gpt-4o-mini")},
-        _RequestExtra(model="gpt-4o", attempt=2),
+        ["gpt-4o", None, 1.5],
+        {"models": ("gpt-4o", "gpt-4o-mini"), "attempt": 2},
+        {"model": "gpt-4o", "status": "ok"},
+        _nest("gpt-4o", 99),
     ),
-    ids=("tuple", "set", "nested_tuple", "dataclass"),
+    ids=("tuple", "list", "nested_tuple", "dict", "deep_list"),
 )
 def test_secret_free_extra_keeps_its_original_object(monkeypatch, extra):
     """A host application's own handler on a litellm logger reads extras by type, so a
@@ -1073,6 +1079,43 @@ def test_extra_that_carried_a_secret_comes_back_scrubbed(monkeypatch, extra):
     assert "REDACTED" in rendered
 
 
+@pytest.mark.parametrize(
+    "extra",
+    (
+        {1: "sk-1234567890abcdefghij"},
+        {"model": {1: "sk-1234567890abcdefghij"}},
+        _nest("sk-1234567890abcdefghij", 101),
+        _RequestExtra(model="gpt-4o", attempt=2, api_key="sk-1234567890abcdefghij"),
+        {"gpt-4o", "sk-1234567890abcdefghij", 1},
+    ),
+    ids=("int_key", "nested_int_key", "deeper_than_safe_dumps", "dataclass_hidden_field", "unsortable_set"),
+)
+def test_extra_the_filter_cannot_fully_inspect_never_keeps_its_secret(monkeypatch, extra):
+    """Whatever safe_dumps would skip (non-string keys, anything past its depth limit,
+    fields a repr hides) must not ride the original object past the redacted stamp."""
+    monkeypatch.setattr("litellm._logging._ENABLE_SECRET_REDACTION", True)
+    record = _make_record(logging.WARNING, "request sent")
+    record.payload = extra
+
+    assert SecretRedactionFilter().filter(record) is True
+    rendered = JsonFormatter().format(record)
+
+    assert record.payload is not extra
+    assert "sk-1234567890abcdefghij" not in str(record.payload)
+    assert "sk-1234567890abcdefghij" not in rendered
+
+
+def test_secret_free_set_comes_back_as_its_json_shape(monkeypatch):
+    monkeypatch.setattr("litellm._logging._ENABLE_SECRET_REDACTION", True)
+    record = _make_record(logging.WARNING, "request sent")
+    record.payload = {"gpt-4o", "gpt-4o-mini"}
+
+    assert SecretRedactionFilter().filter(record) is True
+
+    assert record.payload == ["gpt-4o", "gpt-4o-mini"]
+    assert json.loads(JsonFormatter().format(record))["payload"] == ["gpt-4o", "gpt-4o-mini"]
+
+
 def test_unscrubbed_record_is_still_redacted_by_the_formatter(monkeypatch):
     """Records that never met SecretRedactionFilter (uvicorn's, in JSON mode) keep
     their formatter-side redaction."""