diff --git a/litellm/litellm_core_utils/safe_json_dumps.py b/litellm/litellm_core_utils/safe_json_dumps.py
index 5b99e8cba98..3af400f1a95 100644
--- a/litellm/litellm_core_utils/safe_json_dumps.py
+++ b/litellm/litellm_core_utils/safe_json_dumps.py
@@ -3,6 +3,7 @@ from collections.abc import Callable
 from typing import Any, Final
 
 from pydantic import BaseModel
+from pydantic_core import PydanticSerializationError
 
 from litellm.constants import DEFAULT_MAX_RECURSE_DEPTH
 
@@ -12,6 +13,16 @@ def strip_null_bytes(value: str) -> str:
     return value.replace("\x00", "")
 
 
+def _dump_model(model: BaseModel) -> dict[str, object] | str:
+    try:
+        return model.model_dump()
+    except (PydanticSerializationError, TypeError):
+        try:
+            return model.model_dump(mode="json")
+        except (PydanticSerializationError, TypeError):
+            return str(model)
+
+
 def safe_dumps(
     data: Any,
     max_depth: int = DEFAULT_MAX_RECURSE_DEPTH,
@@ -66,7 +77,7 @@ def safe_dumps(
             seen.remove(id(obj))
             return result
         elif isinstance(obj, BaseModel):
-            dumped: Final = obj.model_dump()
+            dumped: Final = _dump_model(obj)
             result = _serialize(dumped, seen, depth + 1, key)
             seen.remove(id(obj))
             return result
diff --git a/tests/test_litellm/litellm_core_utils/test_safe_json_dumps.py b/tests/test_litellm/litellm_core_utils/test_safe_json_dumps.py
index 30385ba758d..e8cb17f725d 100644
--- a/tests/test_litellm/litellm_core_utils/test_safe_json_dumps.py
+++ b/tests/test_litellm/litellm_core_utils/test_safe_json_dumps.py
@@ -2,10 +2,50 @@ import json
 
 import pytest
 
-
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps, strip_null_bytes
 
 
+@pytest.mark.parametrize("json_succeeds", [True, False])
+def test_repeated_pydantic_model_with_serialization_error(json_succeeds: bool) -> None:
+    from typing import Final
+
+    from pydantic import BaseModel, SerializationInfo, model_serializer
+
+    class FailingModel(BaseModel):
+        value: int = 42
+
+        @model_serializer
+        def serialize_model(self, info: SerializationInfo) -> dict[str, int]:
+            if json_succeeds and info.mode == "json":
+                return {"value": self.value}
+            raise ValueError("serialization failed")
+
+    model: Final = FailingModel()
+    expected: Final = {"value": 42} if json_succeeds else str(model)
+    assert json.loads(safe_dumps([model, model])) == [expected, expected]
+
+
+def test_pydantic_string_fallback_preserves_value_transform() -> None:
+    from typing import Final
+
+    from pydantic import BaseModel, model_serializer
+
+    class FailingModel(BaseModel):
+        @model_serializer
+        def serialize_model(self) -> dict[str, object]:
+            raise ValueError("serialization failed")
+
+        def __str__(self) -> str:
+            return "secret\x00"
+
+    model: Final = FailingModel()
+    assert json.loads(
+        safe_dumps(
+            {"token": model, "other": model}, value_transform=lambda key, value: "redacted" if key == "token" else value
+        )
+    ) == {"token": "redacted", "other": "secret"}
+
+
 def test_primitive_types():
     # Test basic primitive types
     assert safe_dumps("test") == '"test"'
@@ -205,9 +245,7 @@ def test_pydantic_base_model():
         inner: InnerModel
         tags: list
 
-    outer = OuterModel(
-        name="test", inner=InnerModel(value=42, label="hello"), tags=["a", "b"]
-    )
+    outer = OuterModel(name="test", inner=InnerModel(value=42, label="hello"), tags=["a", "b"])
 
     # Test a pydantic model at the top level
     result = json.loads(safe_dumps(outer))