fix(langsmith): json.dumps with default=str so non-serializable metadata does not crash batch flush (#42424)

* fix(langsmith): json.dumps with default=str so non-serializable metadata does not crash batch flush

Serialize the runs/batch payload with json.dumps(default=str, allow_nan=False) and send it as content= with an explicit Content-Type, so datetime, Decimal and similar metadata values no longer raise TypeError and drop the batch. Forward content= on the AsyncHTTPHandler retry path so a retried batch re-sends the identical body

Replaces #39133, which was cut from the retired staging branch and conflicts with main

Co-authored-by: Damien Smrt <dsmrt@users.noreply.github.com>
Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* test(langsmith): drop test docstrings and replace monkeypatch with a client-injecting handler

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* test(langsmith): add live e2e for non-native metadata reaching LangSmith

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* test(langsmith): scope the e2e docstring to the values the test injects

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* test(http_handler): close injected retry clients

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* test(e2e): deselect the LangSmith live e2e on the stage-mirror stack

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

---------

Co-authored-by: yucheng <yucheng@berri.ai>
Co-authored-by: Damien Smrt <dsmrt@users.noreply.github.com>
Co-authored-by: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

.github/e2e-stack/select_tests.py

@@ -10,6 +10,7 @@ UNSUPPORTED: Final = re.compile(
     r"|^tests/e2e/batches/test_managed_files_enforcement_e2e\.py$"
     r"|^tests/e2e/guardrails/test_presidio_masking_e2e\.py$"
     r"|^tests/e2e/logging/test_otel_v2_langfuse_generation_output_e2e\.py$"
+    r"|^tests/e2e/logging/test_langsmith_batch_serialization_e2e\.py$"
 )
 HARNESS: Final = re.compile(
     r"^tests/e2e/[A-Za-z0-9_.-]+\.(py|ini)$"

litellm/integrations/langsmith.py

@@ -1,6 +1,7 @@
 #### What this does ####
 #    On success, logs events to Langsmith
 import asyncio
+import json
 import os
 import random
 import traceback
@@ -415,7 +416,7 @@ class LangsmithLogger(CustomBatchLogger):
         langsmith_api_key: Final = credentials["LANGSMITH_API_KEY"]
         langsmith_tenant_id: Final = credentials.get("LANGSMITH_TENANT_ID")
         url: Final = self._add_endpoint_to_url(langsmith_api_base, "runs/batch")
-        headers: Final = {"x-api-key": langsmith_api_key}
+        headers: Final = {"x-api-key": langsmith_api_key, "Content-Type": "application/json"}
         if langsmith_tenant_id:
             headers["x-tenant-id"] = langsmith_tenant_id
         elements_to_log: Final = [queue_object["data"] for queue_object in queue_objects]
@@ -426,7 +427,7 @@ class LangsmithLogger(CustomBatchLogger):
                 verbose_logger.debug("[LANGSMITH MOCK] Mock mode enabled - API calls will be intercepted")
             response: Final = await self.async_httpx_client.post(
                 url=url,
-                json={"post": elements_to_log},
+                content=json.dumps({"post": elements_to_log}, default=str, allow_nan=False),
                 headers=headers,
             )
             response.raise_for_status()

litellm/llms/custom_httpx/http_handler.py

@@ -845,6 +845,7 @@ class AsyncHTTPHandler:
                     params=params,
                     headers=headers,
                     stream=stream,
+                    content=content,
                 )
             finally:
                 await new_client.aclose()
@@ -985,6 +986,7 @@ class AsyncHTTPHandler:
                     params=params,
                     headers=headers,
                     stream=stream,
+                    content=content,
                 )
             finally:
                 await new_client.aclose()
@@ -1051,6 +1053,7 @@ class AsyncHTTPHandler:
                     params=params,
                     headers=headers,
                     stream=stream,
+                    content=content,
                 )
             finally:
                 await new_client.aclose()

tests/e2e/coverage_registry/logging.yaml

@@ -13,6 +13,7 @@
 - {id: logging.otel.failure.exports_metric, module: logging, tier: P0, event: failure, assertions: [exports_metric], exercised_on: [chat_completions, messages], source: "integrations/otel/logger.py", rationale: "Error spans for observability continuity"}
 - {id: logging.braintrust.success.logs_spend, module: logging, tier: P1, event: success, assertions: [logs_spend], exercised_on: [chat_completions, messages], source: "integrations/braintrust_logging.py", rationale: "Evals platform spend"}
 - {id: logging.langsmith.success.logs_spend, module: logging, tier: P1, event: success, assertions: [logs_spend], exercised_on: [chat_completions, messages], source: "integrations/langsmith.py", rationale: "LangChain ecosystem"}
+- {id: logging.langsmith.success.serializes_non_native_metadata, module: logging, tier: P1, event: success, assertions: [serializes_non_native_metadata], exercised_on: [sdk], source: "integrations/langsmith.py", rationale: "datetime/Decimal/UUID metadata used to TypeError in json.dumps and drop the whole batch (LIT-8310)"}
 - {id: logging.arize.success.logs_spend, module: logging, tier: P1, event: success, assertions: [logs_spend], exercised_on: [chat_completions, embeddings], source: "integrations/arize/arize.py", rationale: "ML-ops observability"}
 - {id: logging.mlflow.success.logs_spend, module: logging, tier: P1, event: success, assertions: [logs_spend], exercised_on: [chat_completions], source: "integrations/mlflow.py", rationale: "Experiment tracking cost/run"}
 - {id: logging.opik.success.logs_spend, module: logging, tier: P1, event: success, assertions: [logs_spend], exercised_on: [chat_completions], source: "integrations/opik/opik.py", rationale: "Eval platform spend/case"}

tests/e2e/logging/test_langsmith_batch_serialization_e2e.py

@@ -0,0 +1,125 @@
+"""Live e2e: a LangSmith batch whose metadata holds non JSON-native Python values
+(datetime, Decimal) must reach the real LangSmith API instead of dying in
+json.dumps and dropping the whole batch. Only the SDK path can put such values
+into the batch (the proxy JSON-decodes request metadata), so this test drives
+litellm.acompletion in-process against the real OpenAI API with a LangsmithLogger
+injected per request, flushes the batch, and reads the run back by id through
+LangSmith's own API. Nothing is mocked.
+"""
+
+from __future__ import annotations
+
+import asyncio
+import datetime
+import decimal
+import os
+import time
+import uuid
+from dataclasses import dataclass
+from typing import Final
+
+import pytest
+from e2e_config import CHEAP_OPENAI_MODEL, POLL_INTERVAL, POLL_TIMEOUT, unique_marker
+from e2e_http import Headers, Success, get_external
+from pydantic import BaseModel, ConfigDict, Field, JsonValue
+
+import litellm
+from litellm.integrations.langsmith import LangsmithLogger
+
+pytestmark = pytest.mark.e2e
+
+
+class LangsmithHeaders(Headers):
+    x_api_key: str = Field(serialization_alias="x-api-key")
+
+
+class LangsmithRunExtra(BaseModel):
+    model_config = ConfigDict(extra="allow")
+    requester_metadata: dict[str, JsonValue] | None = None
+
+
+class LangsmithRun(BaseModel):
+    id: str
+    session_name: str | None = None
+    extra: LangsmithRunExtra
+
+
+@dataclass(frozen=True, slots=True)
+class LangsmithCreds:
+    api_key: str
+    base_url: str
+    project: str
+
+
+def load_langsmith_creds() -> LangsmithCreds:
+    api_key = os.getenv("LANGSMITH_API_KEY")
+    if not api_key:
+        pytest.fail("LangSmith e2e requires LANGSMITH_API_KEY; missing credentials is a hard failure, not a skip")
+    if os.getenv("LANGSMITH_MOCK"):
+        pytest.fail("LANGSMITH_MOCK is set; this e2e must hit the real LangSmith API")
+    return LangsmithCreds(
+        api_key=api_key,
+        base_url=(os.getenv("LANGSMITH_BASE_URL") or "https://api.smith.langchain.com").rstrip("/"),
+        project=os.getenv("LANGSMITH_PROJECT") or "litellm-e2e",
+    )
+
+
+def _fetch_run(creds: LangsmithCreds, run_id: uuid.UUID) -> LangsmithRun | None:
+    result = get_external(
+        f"{creds.base_url}/runs/{run_id}",
+        response_type=LangsmithRun,
+        headers=LangsmithHeaders(x_api_key=creds.api_key),
+    )
+    match result:
+        case Success(data=run):
+            return run
+        case _:
+            return None
+
+
+def _poll_run(creds: LangsmithCreds, run_id: uuid.UUID) -> LangsmithRun:
+    deadline: Final = time.monotonic() + POLL_TIMEOUT
+    while time.monotonic() < deadline:
+        run = _fetch_run(creds, run_id)
+        if run is not None:
+            return run
+        time.sleep(POLL_INTERVAL)
+    pytest.fail(f"LangSmith run {run_id} never appeared within {POLL_TIMEOUT}s; the batch flush dropped it")
+
+
+class TestLangsmithBatchSerialization:
+    @pytest.mark.asyncio
+    @pytest.mark.covers("logging.langsmith.success.serializes_non_native_metadata")
+    async def test_non_json_native_metadata_reaches_langsmith(self) -> None:
+        creds: Final = load_langsmith_creds()
+        logger: Final = LangsmithLogger(
+            langsmith_api_key=creds.api_key, langsmith_project=creds.project, langsmith_base_url=creds.base_url
+        )
+        assert not logger.is_mock_mode, "LangsmithLogger initialised in mock mode; this e2e needs the real API"
+        marker: Final = unique_marker()
+        run_id: Final = uuid.uuid4()
+        created_at: Final = datetime.datetime(2026, 1, 2, 3, 4, 5, tzinfo=datetime.timezone.utc)
+        spend: Final = decimal.Decimal("0.0042")
+        response: Final = await litellm.acompletion(
+            model=f"openai/{CHEAP_OPENAI_MODEL}",
+            messages=[{"role": "user", "content": f"Reply with the single word ok ({marker})"}],
+            max_completion_tokens=5,
+            callbacks=[logger],
+            metadata={"run_id": str(run_id), "metadata": {"marker": marker, "created_at": created_at, "spend": spend}},
+        )
+        assert isinstance(response, litellm.ModelResponse) and response.id, (
+            "a non-streaming completion must return a ModelResponse before the batch flush is meaningful"
+        )
+        enqueue_deadline: Final = time.monotonic() + POLL_TIMEOUT
+        while time.monotonic() < enqueue_deadline and len(logger.log_queue) == 0:
+            await asyncio.sleep(0.5)
+        assert len(logger.log_queue) == 1, (
+            f"the completion must be queued for the LangSmith batch, got {len(logger.log_queue)} queued entries"
+        )
+        await logger.async_send_batch()
+        run: Final = _poll_run(creds, run_id)
+        requester_metadata: Final = run.extra.requester_metadata
+        assert requester_metadata is not None, "the run must carry the caller metadata under extra.requester_metadata"
+        assert requester_metadata["marker"] == marker
+        assert requester_metadata["created_at"] == str(created_at)
+        assert requester_metadata["spend"] == str(spend)

tests/logging_callback_tests/test_langsmith_unit_test.py

@@ -356,10 +356,12 @@ async def test_langsmith_key_based_logging():
         # tenant_id should not be in headers if not provided
         assert "x-tenant-id" not in call_args[1]["headers"]
 
+        assert call_args[1]["headers"]["Content-Type"] == "application/json"
+
         # Verify the request body contains the expected data
-        request_body = call_args[1]["json"]
+        request_body = json.loads(call_args[1]["content"])
         assert "post" in request_body
-        assert len(request_body["post"]) == 1  # Should contain one run
+        assert len(request_body["post"]) == 1
 
         # EXPECTED BODY
         expected_body = {
@@ -404,7 +406,7 @@ async def test_langsmith_key_based_logging():
         }
 
         # Print both bodies for debugging
-        actual_body = call_args[1]["json"]
+        actual_body = json.loads(call_args[1]["content"])
         print("\nExpected body:")
         print(json.dumps(expected_body, indent=2))
         print("\nActual body:")

tests/test_litellm/integrations/test_langsmith_init.py

@@ -1,13 +1,17 @@
 import asyncio
+import json
 import os
+from datetime import datetime, timezone
+from decimal import Decimal
 from typing import Final
 from unittest.mock import AsyncMock, MagicMock, patch
 
+import httpx
 import pytest
 
-
 import litellm
 from litellm.integrations.langsmith import LangsmithLogger
+from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler
 from litellm.types.integrations.langsmith import LangsmithQueueObject
 
 
@@ -219,6 +223,121 @@ class TestLangsmithLoggerInit:
         assert len(logger.log_queue) == 1
 
 
+class TestLangsmithBatchSerialization:
+    async def _logger(self, transport_handler, tenant_id=None):
+        logger = LangsmithLogger(
+            langsmith_api_key="test-key",
+            langsmith_project="test-project",
+            langsmith_base_url="https://api.smith.langchain.com",
+            langsmith_tenant_id=tenant_id,
+        )
+        if logger._flush_task is not None:
+            logger._flush_task.cancel()
+        handler = AsyncHTTPHandler()
+        await handler.client.aclose()
+        handler.client = httpx.AsyncClient(
+            transport=httpx.MockTransport(transport_handler)
+        )
+        logger.async_httpx_client = handler
+        return logger
+
+    @staticmethod
+    def _capturing_transport(captured):
+        async def handle(request: httpx.Request) -> httpx.Response:
+            captured.append(request)
+            return httpx.Response(200, request=request, json={"ok": True})
+
+        return handle
+
+    def _queue(self, logger, extra):
+        return [
+            LangsmithQueueObject(
+                data={"id": "run-1", "name": "LLMRun", "extra": extra},
+                credentials=logger.default_credentials,
+            )
+        ]
+
+    @pytest.mark.asyncio
+    async def test_datetime_and_decimal_metadata_reach_langsmith_as_strings(self):
+        captured: list[httpx.Request] = []  # mutable-ok: transport capture buffer
+        logger = await self._logger(self._capturing_transport(captured))
+        logger.log_queue = self._queue(
+            logger,
+            {
+                "created_at": datetime(2026, 1, 2, 3, 4, 5, tzinfo=timezone.utc),
+                "spend": Decimal("0.0042"),
+            },
+        )
+
+        await logger.async_send_batch()
+
+        assert len(captured) == 1, "batch was dropped instead of being sent"
+        body = json.loads(captured[0].content)
+        assert body["post"][0]["extra"] == {
+            "created_at": "2026-01-02 03:04:05+00:00",
+            "spend": "0.0042",
+        }
+        await logger.async_httpx_client.client.aclose()
+
+    @pytest.mark.asyncio
+    async def test_nan_metadata_is_dropped_instead_of_shipping_invalid_json(self):
+        captured: list[httpx.Request] = []  # mutable-ok: transport capture buffer
+        logger = await self._logger(self._capturing_transport(captured))
+        logger.log_queue = self._queue(logger, {"score": float("nan")})
+
+        await logger.async_send_batch()
+
+        assert captured == [], (
+            "nan metadata must abort the batch: a bare NaN token is invalid JSON and LangSmith rejects it"
+        )
+        await logger.async_httpx_client.client.aclose()
+
+    @pytest.mark.asyncio
+    async def test_batch_declares_json_content_type(self):
+        captured: list[httpx.Request] = []  # mutable-ok: transport capture buffer
+        logger = await self._logger(self._capturing_transport(captured))
+        logger.log_queue = self._queue(logger, {"model": "gpt-4.1-mini"})
+
+        await logger.async_send_batch()
+
+        assert captured[0].headers["content-type"] == "application/json", (
+            "a content= body carries no implicit content type; LangSmith refuses it without this header"
+        )
+        assert captured[0].url.path.endswith("/api/v1/runs/batch")
+        assert captured[0].headers["x-api-key"] == "test-key"
+        assert "x-tenant-id" not in captured[0].headers
+        await logger.async_httpx_client.client.aclose()
+
+    @pytest.mark.asyncio
+    async def test_tenant_id_is_forwarded_on_the_batch_request(self):
+        captured: list[httpx.Request] = []  # mutable-ok: transport capture buffer
+        logger = await self._logger(
+            self._capturing_transport(captured), tenant_id="tenant-1"
+        )
+        logger.log_queue = self._queue(logger, {"model": "gpt-4.1-mini"})
+
+        await logger.async_send_batch()
+
+        assert captured[0].headers["x-tenant-id"] == "tenant-1"
+        await logger.async_httpx_client.client.aclose()
+
+    @pytest.mark.asyncio
+    async def test_langsmith_error_response_does_not_propagate(self):
+        captured: list[httpx.Request] = []  # mutable-ok: transport capture buffer
+
+        async def reject(request: httpx.Request) -> httpx.Response:
+            captured.append(request)
+            return httpx.Response(422, request=request, text="bad run")
+
+        logger = await self._logger(reject)
+        logger.log_queue = self._queue(logger, {"model": "gpt-4.1-mini"})
+
+        await logger.async_send_batch()
+
+        assert len(captured) == 1, "the batch never left the process"
+        await logger.async_httpx_client.client.aclose()
+
+
 class TestLangsmithPrepareLogData:
     """Regression test for #24001: _prepare_log_data must inject
     usage_metadata into outputs so LangSmith's Cost column is populated."""
@@ -544,12 +663,10 @@ async def test_events_appended_during_flush_are_not_dropped():
             credentials=logger.default_credentials, data={"id": "late"}
         )
 
-        async def fake_post(
-            url: str, json: dict[str, list[dict[str, str]]], headers: dict[str, str]
-        ) -> MagicMock:
+        async def fake_post(url: str, content: str, headers: dict[str, str]) -> MagicMock:
             if not sent_batches:
                 logger.log_queue.append(late_event)
-            sent_batches.append(json["post"])
+            sent_batches.append(json.loads(content)["post"])
             response = MagicMock()
             response.status_code = 200
             response.raise_for_status = MagicMock()

tests/test_litellm/llms/custom_httpx/test_http_handler.py

@@ -6,6 +6,8 @@ import pathlib
 import ssl
 import threading
 import weakref
+from collections.abc import Callable, Mapping
+from typing import Final
 from unittest.mock import MagicMock, patch
 
 import certifi
@@ -23,6 +25,7 @@ from litellm.llms.custom_httpx.http_handler import (
     _get_httpx_client,
     get_ssl_configuration,
 )
+from litellm.types.llms.custom_http import VerifyTypes
 
 
 @pytest.mark.asyncio
@@ -1396,6 +1399,47 @@ async def test_finalizer_on_live_loop_disposes_foreign_loop_session_without_sche
     assert session.closed
 
 
+class _RetryClientHandler(AsyncHTTPHandler):
+    def __init__(self, first: httpx.AsyncClient, retry: httpx.AsyncClient) -> None:
+        self._retry_client: Final = retry
+        super().__init__()
+        self.client = first
+
+    def create_client(
+        self,
+        timeout: float | httpx.Timeout | None = None,
+        event_hooks: Mapping[str, list[Callable[..., object]]] | None = None,
+        ssl_verify: VerifyTypes | None = None,
+        shared_session: ClientSession | None = None,
+    ) -> httpx.AsyncClient:
+        return self._retry_client
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("method", ["post", "put", "patch", "delete"])
+async def test_connection_error_retry_forwards_content(method: str):
+    captured: list[bytes] = []  # mutable-ok: async closure capture buffer
+
+    async def raise_connection_error(request: httpx.Request) -> httpx.Response:
+        raise httpx.RemoteProtocolError("connection dropped", request=request)
+
+    async def capture_and_succeed(request: httpx.Request) -> httpx.Response:
+        captured.append(request.content)
+        return httpx.Response(200, request=request)
+
+    first: Final = httpx.AsyncClient(transport=httpx.MockTransport(raise_connection_error))
+    retry: Final = httpx.AsyncClient(transport=httpx.MockTransport(capture_and_succeed))
+    async with first, retry:
+        handler: Final = _RetryClientHandler(first=first, retry=retry)
+
+        body = b'{"post": ["run1"]}'
+        await getattr(handler, method)("https://api.example.com/runs/batch", content=body)
+
+        assert captured == [body], "the retried request must carry the same content= body"
+        await handler.close()
+
+
+
 @pytest.fixture
 def forward_proxy_server():
     """Plain HTTP forward proxy that records the absolute URIs it is asked to fetch."""