From ffc530be44c0d00a88b6d34643c0c8e05276f951 Mon Sep 17 00:00:00 2001
From: William Fu-Hinthorn <13333726+hinthornw@users.noreply.github.com>
Date: Mon, 9 Dec 2024 07:41:54 -0800
Subject: [PATCH] Broader catch in post/patch

---
 python/langsmith/_internal/_operations.py |  26 +++++-
 python/langsmith/run_trees.py             | 104 ++++++++++++----------
 2 files changed, 78 insertions(+), 52 deletions(-)

diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index 66decff0f..a97dec161 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -123,6 +123,26 @@ def serialize_feedback_dict(
     )
 
 
+def _dumps_json_safe(value: object, which: str) -> bytes:
+    try:
+        return _dumps_json(value)
+    except Exception as e:
+        logger.warning(f"Error serializing {which}: {e}")
+        try:
+            return _dumps_json(
+                {
+                    "langsmith_serialization_error": f"Error serializing {which}:"
+                    f" {str(e)}\n\n{value}"
+                }
+            )
+        except Exception:
+            return _dumps_json(
+                {
+                    "langsmith_serialization_error": f"Error serializing {which}: {str(e)}"
+                }
+            )
+
+
 def serialize_run_dict(
     operation: Literal["post", "patch"], payload: dict
 ) -> SerializedRunOperation:
@@ -135,9 +155,9 @@ def serialize_run_dict(
         id=payload["id"],
         trace_id=payload["trace_id"],
         _none=_dumps_json(payload),
-        inputs=_dumps_json(inputs) if inputs is not None else None,
-        outputs=_dumps_json(outputs) if outputs is not None else None,
-        events=_dumps_json(events) if events is not None else None,
+        inputs=_dumps_json_safe(inputs, "inputs") if inputs is not None else None,
+        outputs=_dumps_json_safe(outputs, "outputs") if outputs is not None else None,
+        events=_dumps_json_safe(events, "events") if events is not None else None,
         attachments=attachments if attachments is not None else None,
     )
 
diff --git a/python/langsmith/run_trees.py b/python/langsmith/run_trees.py
index 63f0cb4e5..fcef5ab7b 100644
--- a/python/langsmith/run_trees.py
+++ b/python/langsmith/run_trees.py
@@ -299,60 +299,66 @@ def _get_dicts_safe(self):
 
     def post(self, exclude_child_runs: bool = True) -> None:
         """Post the run tree to the API asynchronously."""
-        kwargs = self._get_dicts_safe()
-        self.client.create_run(**kwargs)
-        if attachments := kwargs.get("attachments"):
-            keys = [str(name) for name in attachments]
-            self.events.append(
-                {
-                    "name": "uploaded_attachment",
-                    "time": datetime.now(timezone.utc).isoformat(),
-                    "message": set(keys),
-                }
-            )
-        if not exclude_child_runs:
-            for child_run in self.child_runs:
-                child_run.post(exclude_child_runs=False)
+        try:
+            kwargs = self._get_dicts_safe()
+            self.client.create_run(**kwargs)
+            if attachments := kwargs.get("attachments"):
+                keys = [str(name) for name in attachments]
+                self.events.append(
+                    {
+                        "name": "uploaded_attachment",
+                        "time": datetime.now(timezone.utc).isoformat(),
+                        "message": set(keys),
+                    }
+                )
+            if not exclude_child_runs:
+                for child_run in self.child_runs:
+                    child_run.post(exclude_child_runs=False)
+        except Exception as e:
+            logger.warning(f"Error creating run: {e}")
 
     def patch(self) -> None:
         """Patch the run tree to the API in a background thread."""
-        if not self.end_time:
-            self.end()
-        attachments = self.attachments
         try:
-            # Avoid loading the same attachment twice
-            if attachments:
-                uploaded = next(
-                    (
-                        ev
-                        for ev in self.events
-                        if ev.get("name") == "uploaded_attachment"
-                    ),
-                    None,
-                )
-                if uploaded:
-                    attachments = {
-                        a: v
-                        for a, v in attachments.items()
-                        if a not in uploaded["message"]
-                    }
+            if not self.end_time:
+                self.end()
+            attachments = self.attachments
+            try:
+                # Avoid loading the same attachment twice
+                if attachments:
+                    uploaded = next(
+                        (
+                            ev
+                            for ev in self.events
+                            if ev.get("name") == "uploaded_attachment"
+                        ),
+                        None,
+                    )
+                    if uploaded:
+                        attachments = {
+                            a: v
+                            for a, v in attachments.items()
+                            if a not in uploaded["message"]
+                        }
+            except Exception as e:
+                logger.warning(f"Error filtering attachments to upload: {e}")
+            self.client.update_run(
+                name=self.name,
+                run_id=self.id,
+                outputs=self.outputs.copy() if self.outputs else None,
+                error=self.error,
+                parent_run_id=self.parent_run_id,
+                reference_example_id=self.reference_example_id,
+                end_time=self.end_time,
+                dotted_order=self.dotted_order,
+                trace_id=self.trace_id,
+                events=self.events,
+                tags=self.tags,
+                extra=self.extra,
+                attachments=attachments,
+            )
         except Exception as e:
-            logger.warning(f"Error filtering attachments to upload: {e}")
-        self.client.update_run(
-            name=self.name,
-            run_id=self.id,
-            outputs=self.outputs.copy() if self.outputs else None,
-            error=self.error,
-            parent_run_id=self.parent_run_id,
-            reference_example_id=self.reference_example_id,
-            end_time=self.end_time,
-            dotted_order=self.dotted_order,
-            trace_id=self.trace_id,
-            events=self.events,
-            tags=self.tags,
-            extra=self.extra,
-            attachments=attachments,
-        )
+            logger.warning(f"Error updating run: {e}")
 
     def wait(self) -> None:
         """Wait for all _futures to complete."""