diff --git a/litellm/_logging.py b/litellm/_logging.py
index d01960ed7ac..28c5b4d8b46 100644
--- a/litellm/_logging.py
+++ b/litellm/_logging.py
@@ -18,7 +18,7 @@ from litellm.constants import (
     MAX_STRING_LENGTH_STDOUT_LOG,
 )
 from litellm.litellm_core_utils.env_utils import get_env_int
-from litellm.litellm_core_utils.safe_json_dumps import safe_dumps, safe_json_structure
+from litellm.litellm_core_utils.safe_json_dumps import UNSERIALIZABLE_OBJECT, safe_dumps, safe_json_structure
 from litellm.litellm_core_utils.safe_json_loads import safe_json_loads
 from litellm.litellm_core_utils.secret_redaction import (
     redact_internal_details,
@@ -94,11 +94,18 @@ def _scrubbing_changed_nothing(scrubbed: object, original: object) -> bool:
         return False
 
 
+def _plain_text(value: object) -> str:
+    try:
+        return str(value)
+    except Exception:
+        return UNSERIALIZABLE_OBJECT
+
+
 def _redact_extra_value(key: str, value: object) -> object:
     try:
         scrubbed: Final = safe_json_structure(value, value_transform=_redact_structured_value, key=key)
-    except (TypeError, ValueError):
-        return _redact_string(str(value))
+    except Exception:
+        return _redact_string(_plain_text(value))
     return value if _scrubbing_changed_nothing(scrubbed, value) else scrubbed
 
 
@@ -151,7 +158,7 @@ class SecretRedactionFilter(logging.Filter):
     _formatter = logging.Formatter()
 
     def filter(self, record: logging.LogRecord) -> bool:
-        if not _ENABLE_SECRET_REDACTION:
+        if not _ENABLE_SECRET_REDACTION or _is_redacted(record):
             return True
 
         # Runs before args are cleared, and before the extra-field loop below
diff --git a/litellm/litellm_core_utils/safe_json_dumps.py b/litellm/litellm_core_utils/safe_json_dumps.py
index 7cc47b2d6c3..4f9ac82d57d 100644
--- a/litellm/litellm_core_utils/safe_json_dumps.py
+++ b/litellm/litellm_core_utils/safe_json_dumps.py
@@ -6,6 +6,8 @@ from pydantic import BaseModel
 
 from litellm.constants import DEFAULT_MAX_RECURSE_DEPTH
 
+UNSERIALIZABLE_OBJECT: Final = "Unserializable Object"
+
 
 def strip_null_bytes(value: str) -> str:
     """Strip NUL bytes, which PostgreSQL text/jsonb columns reject (error 22P05)."""
@@ -77,7 +79,7 @@ def safe_json_structure(
             try:
                 return _transform(key, strip_null_bytes(str(obj)))
             except Exception:
-                return "Unserializable Object"
+                return UNSERIALIZABLE_OBJECT
 
     return _serialize(data, set(), 0, key)
 
diff --git a/tests/test_litellm/test_logging.py b/tests/test_litellm/test_logging.py
index 18fb86e5a2a..eeb30f813bf 100644
--- a/tests/test_litellm/test_logging.py
+++ b/tests/test_litellm/test_logging.py
@@ -12,6 +12,7 @@ from pathlib import Path
 from typing import List
 
 import pytest
+from pydantic import BaseModel, computed_field
 
 import litellm
 from litellm._logging import (
@@ -1000,6 +1001,20 @@ def test_scrubbed_record_is_scanned_for_secrets_once(monkeypatch, formatter):
     assert counting.scanned_chars == len(f"receiving data: {_REQUEST_DUMP}")
 
 
+def test_stamped_record_is_not_scanned_again(monkeypatch):
+    """JSON mode puts the filter on a third-party logger and again on the root handler its
+    records propagate to, so the second filter must trust the stamp instead of rescanning."""
+    counting = _CountingPattern(secret_redaction._SECRET_RE)
+    monkeypatch.setattr(secret_redaction, "_SECRET_RE", counting)
+    monkeypatch.setattr("litellm._logging._ENABLE_SECRET_REDACTION", True)
+    record = _make_record(logging.DEBUG, "receiving data: %s", (_REQUEST_DUMP,))
+
+    assert SecretRedactionFilter().filter(record) is True
+    assert SecretRedactionFilter().filter(record) is True
+
+    assert counting.calls == 1
+
+
 def test_stack_info_is_scrubbed_before_the_plain_formatter(monkeypatch):
     monkeypatch.setattr("litellm._logging._ENABLE_SECRET_REDACTION", True)
     record = _make_record(logging.INFO, "call failed")
@@ -1012,8 +1027,23 @@ def test_stack_info_is_scrubbed_before_the_plain_formatter(monkeypatch):
     assert "Stack (most recent call last):" in rendered
 
 
-@pytest.mark.parametrize("extra", ({1, "a"}, {"nested": {1, "a"}}), ids=("mixed_set", "nested_mixed_set"))
+class _BrokenModel(BaseModel):
+    name: str
+
+    @computed_field
+    @property
+    def snapshot(self) -> str:
+        raise RuntimeError("snapshot unavailable")
+
+
+@pytest.mark.parametrize(
+    "extra",
+    ({1, "a"}, {"nested": {1, "a"}}, _BrokenModel(name="gpt-4o"), {"request": _BrokenModel(name="gpt-4o")}),
+    ids=("mixed_set", "nested_mixed_set", "raising_model", "nested_raising_model"),
+)
 def test_unserializable_extra_never_breaks_the_filter(monkeypatch, extra):
+    """A pydantic computed field that raises escapes model_dump() and str() alike, and a
+    logging filter that lets it through raises into the caller's own log call."""
     monkeypatch.setattr("litellm._logging._ENABLE_SECRET_REDACTION", True)
     record = _make_record(logging.WARNING, "request sent")
     record.payload = extra