From a5efbb80480c63c91f6fd5ea77b73c6709d985a2 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 16:10:16 -0800
Subject: [PATCH 01/56] start of compression

---
 .../langsmith/_internal/_background_thread.py | 45 +++++++++++++++++
 python/langsmith/_internal/_operations.py     | 34 +++++++++++++
 python/langsmith/client.py                    | 48 ++++++++++++++++---
 3 files changed, 120 insertions(+), 7 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index c0f3d46ab..a53209abf 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -1,14 +1,18 @@
 from __future__ import annotations
 
 import functools
+import io
 import logging
 import sys
 import threading
+import time
 import weakref
+import zstandard as zstd
 from queue import Empty, Queue
 from typing import (
     TYPE_CHECKING,
     List,
+    Optional,
     Union,
     cast,
 )
@@ -88,6 +92,34 @@ def _tracing_thread_drain_queue(
     return next_batch
 
 
+def _tracing_thread_drain_compressed_buffer(
+    client: Client,
+    runs_limit: int = 100,
+    max_buffer_size: int = 50 * 1024 * 1024
+) -> Optional[bytes]:
+    with client._buffer_lock:
+        current_size = client.tracing_queue.tell()
+
+        # Check if we should send now
+        if not (client._run_count >= runs_limit or current_size >= max_buffer_size):
+            return None
+
+        # Write final boundary and close compression stream
+        client.compressor_writer.write(f'--{client.boundary}--\r\n'.encode())
+        client.compressor_writer.flush()
+        client.compressor_writer.close()
+
+        client.tracing_queue.seek(0)
+        data = client.tracing_queue.getvalue()
+
+        # Reinitialize for next batch
+        client.tracing_queue = io.BytesIO()
+        client.compressor = zstd.ZstdCompressor()
+        client.compressor_writer = client.compressor.stream_writer(
+            client.tracing_queue, closefd=False)
+        client._run_count = 0
+        return data
+
 def _tracing_thread_handle_batch(
     client: Client,
     tracing_queue: Queue,
@@ -199,6 +231,19 @@ def keep_thread_active() -> bool:
     ):
         _tracing_thread_handle_batch(client, tracing_queue, next_batch, use_multipart)
 
+def tracing_control_thread_func_compress(client_ref: weakref.ref[Client]) -> None:
+    client = client_ref()
+    if client is None:
+        return
+
+    while True:
+        result = _tracing_thread_drain_compressed_buffer(client)
+        if result is not None:
+            time.sleep(0.150)  # Simulate call to backend
+        else:
+            time.sleep(0.1)  # Avoid busy-waiting if no data ready
+
+
 
 def _tracing_sub_thread_func(
     client_ref: weakref.ref[Client],
diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index 66decff0f..96b33a6af 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -3,6 +3,8 @@
 import itertools
 import logging
 import uuid
+import io
+import zstandard
 from typing import Literal, Optional, Union, cast
 
 from langsmith import schemas as ls_schemas
@@ -271,3 +273,35 @@ def serialized_run_operation_to_multipart_parts_and_context(
         acc_parts,
         f"trace={op.trace_id},id={op.id}",
     )
+
+
+def write_multipart_parts_to_compressor(
+    parts_and_context: MultipartPartsAndContext,
+    compressor_writer: zstandard.ZstdCompressorWriter,
+    boundary: str
+) -> None:
+    compressor_writer.write(f'--{boundary}\r\n'.encode())
+
+    for part_name, (filename, data, content_type, headers) in parts_and_context.parts:
+        part_header = f'Content-Disposition: form-data; name="{part_name}"'
+        if filename:
+            part_header += f'; filename="{filename}"'
+        part_header += f'\r\nContent-Type: {content_type}\r\n'
+
+        for header_name, header_value in headers.items():
+            part_header += f'{header_name}: {header_value}\r\n'
+
+        part_header += '\r\n'
+        compressor_writer.write(part_header.encode())
+
+        if isinstance(data, (bytes, bytearray)):
+            with memoryview(data) as view:
+                chunk_size = 1024 * 1024  # 1MB chunks
+                for i in range(0, len(view), chunk_size):
+                    chunk = view[i:i + chunk_size]
+                    compressor_writer.write(chunk)
+        else:
+            compressor_writer.write(str(data).encode())
+
+        compressor_writer.write(b'\r\n')
+
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 1d27e7c99..324753e86 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -33,6 +33,7 @@
 import uuid
 import warnings
 import weakref
+import zstandard
 from inspect import signature
 from queue import PriorityQueue
 from typing import (
@@ -75,6 +76,7 @@
 )
 from langsmith._internal._background_thread import (
     tracing_control_thread_func as _tracing_control_thread_func,
+    tracing_control_thread_func_compress as _tracing_control_thread_func_compress
 )
 from langsmith._internal._beta_decorator import warn_beta
 from langsmith._internal._constants import (
@@ -94,6 +96,7 @@
     serialize_run_dict,
     serialized_feedback_operation_to_multipart_parts_and_context,
     serialized_run_operation_to_multipart_parts_and_context,
+    write_multipart_parts_to_compressor,
 )
 from langsmith._internal._serde import dumps_json as _dumps_json
 
@@ -489,6 +492,15 @@ def __init__(
         # Create a session and register a finalizer to close it
         session_ = session if session else requests.Session()
         self.session = session_
+        self.compress_traces = os.getenv("LANGSMITH_COMPRESS_TRACES") == "true"
+        if self.compress_traces:
+            self.compressor = zstandard.ZstdCompressor()
+            self.compressor_writer = self.compressor.stream_writer(
+                self.tracing_queue, closefd=False)
+            self.tracing_queue = io.BytesIO()
+            self._buffer_lock = threading.Lock()
+            self._run_count = 0
+            
         self._info = (
             info
             if info is None or isinstance(info, ls_schemas.LangSmithInfo)
@@ -497,7 +509,14 @@ def __init__(
         weakref.finalize(self, close_session, self.session)
         atexit.register(close_session, session_)
         # Initialize auto batching
-        if auto_batch_tracing:
+        if auto_batch_tracing and self.compress_traces:
+            threading.Thread(
+                target=_tracing_control_thread_func_compress,
+                # arg must be a weakref to self to avoid the Thread object
+                # preventing garbage collection of the Client object
+                args=(weakref.ref(self),),
+            ).start()
+        elif auto_batch_tracing:
             self.tracing_queue: Optional[PriorityQueue] = PriorityQueue()
 
             threading.Thread(
@@ -1291,9 +1310,17 @@ def create_run(
                 self._pyo3_client.create_run(run_create)
             elif self.tracing_queue is not None:
                 serialized_op = serialize_run_dict("post", run_create)
-                self.tracing_queue.put(
-                    TracingQueueItem(run_create["dotted_order"], serialized_op)
-                )
+                if self.compress_traces:
+                    multipart_form = self.serialized_run_operation_to_multipart_parts_and_context(
+                        serialized_op)
+                    with self._buffer_lock:
+                        write_multipart_parts_to_compressor(
+                            multipart_form, self.compressor_writer, self.boundary)
+                        self._run_count += 1
+                else:
+                    self.tracing_queue.put(
+                        TracingQueueItem(run_create["dotted_order"], serialized_op)
+                    )
             else:
                 # Neither Rust nor Python batch ingestion is configured,
                 # fall back to the non-batch approach.
@@ -1755,9 +1782,16 @@ def update_run(
         if use_multipart and self.tracing_queue is not None:
             # not collecting attachments currently, use empty dict
             serialized_op = serialize_run_dict(operation="patch", payload=data)
-            self.tracing_queue.put(
-                TracingQueueItem(data["dotted_order"], serialized_op)
-            )
+            if self.compress_traces:
+                multipart_form = serialized_run_operation_to_multipart_parts_and_context(serialized_op)
+                with self._buffer_lock:
+                    write_multipart_parts_to_compressor(
+                        multipart_form, self.compressor_writer, self.boundary)
+                    self._run_count += 1
+            else:
+                self.tracing_queue.put(
+                    TracingQueueItem(data["dotted_order"], serialized_op)
+                )
         else:
             self._update_run(data)
 

From c10a8ad6d4fe1d1aedbef0b46dfdf881a1f25367 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 16:25:40 -0800
Subject: [PATCH 02/56] manually encode

---
 python/langsmith/_internal/_operations.py | 21 +++++++++++----------
 python/langsmith/client.py                |  6 +++---
 2 files changed, 14 insertions(+), 13 deletions(-)

diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index 96b33a6af..a19640289 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -275,25 +275,26 @@ def serialized_run_operation_to_multipart_parts_and_context(
     )
 
 
-def write_multipart_parts_to_compressor(
-    parts_and_context: MultipartPartsAndContext,
+def compress_multipart_parts_and_context(
+    parts_and_context: MultipartPartsAndContext, 
     compressor_writer: zstandard.ZstdCompressorWriter,
     boundary: str
 ) -> None:
-    compressor_writer.write(f'--{boundary}\r\n'.encode())
-
     for part_name, (filename, data, content_type, headers) in parts_and_context.parts:
-        part_header = f'Content-Disposition: form-data; name="{part_name}"'
+        part_header = f'--{boundary}\r\n'
+        part_header += f'Content-Disposition: form-data; name="{part_name}"'
+        
         if filename:
             part_header += f'; filename="{filename}"'
+        
         part_header += f'\r\nContent-Type: {content_type}\r\n'
-
+        
         for header_name, header_value in headers.items():
             part_header += f'{header_name}: {header_value}\r\n'
-
+        
         part_header += '\r\n'
         compressor_writer.write(part_header.encode())
-
+        
         if isinstance(data, (bytes, bytearray)):
             with memoryview(data) as view:
                 chunk_size = 1024 * 1024  # 1MB chunks
@@ -302,6 +303,6 @@ def write_multipart_parts_to_compressor(
                     compressor_writer.write(chunk)
         else:
             compressor_writer.write(str(data).encode())
-
+        
+        # Write part terminator
         compressor_writer.write(b'\r\n')
-
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 324753e86..b0d6a88ae 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -96,7 +96,7 @@
     serialize_run_dict,
     serialized_feedback_operation_to_multipart_parts_and_context,
     serialized_run_operation_to_multipart_parts_and_context,
-    write_multipart_parts_to_compressor,
+    compress_multipart_parts_and_context,
 )
 from langsmith._internal._serde import dumps_json as _dumps_json
 
@@ -1314,7 +1314,7 @@ def create_run(
                     multipart_form = self.serialized_run_operation_to_multipart_parts_and_context(
                         serialized_op)
                     with self._buffer_lock:
-                        write_multipart_parts_to_compressor(
+                        compress_multipart_parts_and_context(
                             multipart_form, self.compressor_writer, self.boundary)
                         self._run_count += 1
                 else:
@@ -1785,7 +1785,7 @@ def update_run(
             if self.compress_traces:
                 multipart_form = serialized_run_operation_to_multipart_parts_and_context(serialized_op)
                 with self._buffer_lock:
-                    write_multipart_parts_to_compressor(
+                    compress_multipart_parts_and_context(
                         multipart_form, self.compressor_writer, self.boundary)
                     self._run_count += 1
             else:

From d456776c4d128d2077eab11ad31deecd3da42bd1 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 16:40:19 -0800
Subject: [PATCH 03/56] set boundary

---
 python/langsmith/client.py | 1 +
 1 file changed, 1 insertion(+)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index b0d6a88ae..daf113bb5 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -494,6 +494,7 @@ def __init__(
         self.session = session_
         self.compress_traces = os.getenv("LANGSMITH_COMPRESS_TRACES") == "true"
         if self.compress_traces:
+            self.boundary = BOUNDARY
             self.compressor = zstandard.ZstdCompressor()
             self.compressor_writer = self.compressor.stream_writer(
                 self.tracing_queue, closefd=False)

From 0359235b15a9b773ce96beee41d852d62013eb41 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 17:11:16 -0800
Subject: [PATCH 04/56] add zstandard

---
 python/poetry.lock    | 206 +++++++++++++++++++++++++++++++++++++++++-
 python/pyproject.toml |   1 +
 2 files changed, 205 insertions(+), 2 deletions(-)

diff --git a/python/poetry.lock b/python/poetry.lock
index 77d4b5c08..de2ec943d 100644
--- a/python/poetry.lock
+++ b/python/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry 1.8.2 and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.8.4 and should not be changed by hand.
 
 [[package]]
 name = "annotated-types"
@@ -109,6 +109,85 @@ files = [
     {file = "certifi-2024.8.30.tar.gz", hash = "sha256:bec941d2aa8195e248a60b31ff9f0558284cf01a52591ceda73ea9afffd69fd9"},
 ]
 
+[[package]]
+name = "cffi"
+version = "1.17.1"
+description = "Foreign Function Interface for Python calling C code."
+optional = false
+python-versions = ">=3.8"
+files = [
+    {file = "cffi-1.17.1-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:df8b1c11f177bc2313ec4b2d46baec87a5f3e71fc8b45dab2ee7cae86d9aba14"},
+    {file = "cffi-1.17.1-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:8f2cdc858323644ab277e9bb925ad72ae0e67f69e804f4898c070998d50b1a67"},
+    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_12_i686.manylinux2010_i686.manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:edae79245293e15384b51f88b00613ba9f7198016a5948b5dddf4917d4d26382"},
+    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:45398b671ac6d70e67da8e4224a065cec6a93541bb7aebe1b198a61b58c7b702"},
+    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:ad9413ccdeda48c5afdae7e4fa2192157e991ff761e7ab8fdd8926f40b160cc3"},
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+    {file = "zstandard-0.23.0-cp38-cp38-win32.whl", hash = "sha256:b8c0bd73aeac689beacd4e7667d48c299f61b959475cdbb91e7d3d88d27c56b9"},
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+    {file = "zstandard-0.23.0-cp39-cp39-musllinux_1_1_aarch64.whl", hash = "sha256:2fb4535137de7e244c230e24f9d1ec194f61721c86ebea04e1581d9d06ea1269"},
+    {file = "zstandard-0.23.0-cp39-cp39-musllinux_1_1_x86_64.whl", hash = "sha256:8c24f21fa2af4bb9f2c492a86fe0c34e6d2c63812a839590edaf177b7398f700"},
+    {file = "zstandard-0.23.0-cp39-cp39-musllinux_1_2_aarch64.whl", hash = "sha256:a8c86881813a78a6f4508ef9daf9d4995b8ac2d147dcb1a450448941398091c9"},
+    {file = "zstandard-0.23.0-cp39-cp39-musllinux_1_2_i686.whl", hash = "sha256:fe3b385d996ee0822fd46528d9f0443b880d4d05528fd26a9119a54ec3f91c69"},
+    {file = "zstandard-0.23.0-cp39-cp39-musllinux_1_2_ppc64le.whl", hash = "sha256:82d17e94d735c99621bf8ebf9995f870a6b3e6d14543b99e201ae046dfe7de70"},
+    {file = "zstandard-0.23.0-cp39-cp39-musllinux_1_2_s390x.whl", hash = "sha256:c7c517d74bea1a6afd39aa612fa025e6b8011982a0897768a2f7c8ab4ebb78a2"},
+    {file = "zstandard-0.23.0-cp39-cp39-musllinux_1_2_x86_64.whl", hash = "sha256:1fd7e0f1cfb70eb2f95a19b472ee7ad6d9a0a992ec0ae53286870c104ca939e5"},
+    {file = "zstandard-0.23.0-cp39-cp39-win32.whl", hash = "sha256:43da0f0092281bf501f9c5f6f3b4c975a8a0ea82de49ba3f7100e64d422a1274"},
+    {file = "zstandard-0.23.0-cp39-cp39-win_amd64.whl", hash = "sha256:f8346bfa098532bc1fb6c7ef06783e969d87a99dd1d2a5a18a892c1d7a643c58"},
+    {file = "zstandard-0.23.0.tar.gz", hash = "sha256:b2d8c62d08e7255f68f7a740bae85b3c9b8e5466baa9cbf7f57f1cde0ac6bc09"},
+]
+
+[package.dependencies]
+cffi = {version = ">=1.11", markers = "platform_python_implementation == \"PyPy\""}
+
+[package.extras]
+cffi = ["cffi (>=1.11)"]
+
 [extras]
 langsmith-pyo3 = ["langsmith-pyo3"]
 vcr = []
@@ -2113,4 +2315,4 @@ vcr = []
 [metadata]
 lock-version = "2.0"
 python-versions = ">=3.9,<4.0"
-content-hash = "c7acc8c8f123bf7968b265a0f0cdd0b679d88559bfbff33488bff25bb4f54f0f"
+content-hash = "7b8c702e50f6ae0f5a81bd2da1d6e0277f7fd28c5d02b2d62571573d3ae9f358"
diff --git a/python/pyproject.toml b/python/pyproject.toml
index a831ff0df..89df9dff8 100644
--- a/python/pyproject.toml
+++ b/python/pyproject.toml
@@ -37,6 +37,7 @@ requests-toolbelt = "^1.0.0"
 
 # Enabled via `langsmith_pyo3` extra: `pip install langsmith[langsmith_pyo3]`.
 langsmith-pyo3 = { version = "^0.1.0rc2", optional = true }
+zstandard = "^0.23.0"
 
 [tool.poetry.group.dev.dependencies]
 pytest = "^7.3.1"

From 08bce98a88512cf00383e454806b428314421688 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 17:16:06 -0800
Subject: [PATCH 05/56] set limits from config

---
 python/langsmith/_internal/_background_thread.py | 15 +++++++++------
 1 file changed, 9 insertions(+), 6 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index a53209abf..f7ebbc884 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -94,14 +94,14 @@ def _tracing_thread_drain_queue(
 
 def _tracing_thread_drain_compressed_buffer(
     client: Client,
-    runs_limit: int = 100,
-    max_buffer_size: int = 50 * 1024 * 1024
+    size_limit: int = 100,
+    size_limit_bytes: int = 50 * 1024 * 1024
 ) -> Optional[bytes]:
     with client._buffer_lock:
         current_size = client.tracing_queue.tell()
 
         # Check if we should send now
-        if not (client._run_count >= runs_limit or current_size >= max_buffer_size):
+        if not (client._run_count >= size_limit or current_size >= size_limit_bytes):
             return None
 
         # Write final boundary and close compression stream
@@ -155,7 +155,7 @@ def _ensure_ingest_config(
 ) -> ls_schemas.BatchIngestConfig:
     default_config = ls_schemas.BatchIngestConfig(
         use_multipart_endpoint=False,
-        size_limit_bytes=None,  # Note this field is not used here
+        size_limit_bytes=50 * 1024 * 1024,
         size_limit=100,
         scale_up_nthreads_limit=_AUTO_SCALE_UP_NTHREADS_LIMIT,
         scale_up_qsize_trigger=_AUTO_SCALE_UP_QSIZE_TRIGGER,
@@ -235,9 +235,12 @@ def tracing_control_thread_func_compress(client_ref: weakref.ref[Client]) -> Non
     client = client_ref()
     if client is None:
         return
-
+    batch_ingest_config = _ensure_ingest_config(client.info)
+    size_limit: int = batch_ingest_config["size_limit"]
+    size_limit_bytes: int = batch_ingest_config["size_limit_bytes"]
+    
     while True:
-        result = _tracing_thread_drain_compressed_buffer(client)
+        result = _tracing_thread_drain_compressed_buffer(client, size_limit, size_limit_bytes)
         if result is not None:
             time.sleep(0.150)  # Simulate call to backend
         else:

From 800472a01ae80e24044fb8341307c8cbf3d37d00 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 17:22:35 -0800
Subject: [PATCH 06/56] add slots

---
 python/langsmith/client.py | 7 +++++++
 1 file changed, 7 insertions(+)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index daf113bb5..c6fb5714d 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -391,6 +391,13 @@ class Client:
         "_settings",
         "_manual_cleanup",
         "_pyo3_client",
+        "compress_traces",
+        "boundary",
+        "compressor",
+        "compressor_writer",
+        "tracing_queue",
+        "_run_count",
+        "_buffer_lock",
     ]
 
     def __init__(

From d4e45e1bcde471848745dd21f3c288912bd343c5 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 17:26:41 -0800
Subject: [PATCH 07/56] lint

---
 python/langsmith/_internal/_background_thread.py | 6 ++++--
 python/langsmith/_internal/_operations.py        | 4 ++--
 python/langsmith/client.py                       | 8 +++++---
 3 files changed, 11 insertions(+), 7 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index f7ebbc884..5e986ac9e 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -7,7 +7,6 @@
 import threading
 import time
 import weakref
-import zstandard as zstd
 from queue import Empty, Queue
 from typing import (
     TYPE_CHECKING,
@@ -17,6 +16,8 @@
     cast,
 )
 
+import zstandard as zstd
+
 from langsmith import schemas as ls_schemas
 from langsmith._internal._constants import (
     _AUTO_SCALE_DOWN_NEMPTY_TRIGGER,
@@ -240,7 +241,8 @@ def tracing_control_thread_func_compress(client_ref: weakref.ref[Client]) -> Non
     size_limit_bytes: int = batch_ingest_config["size_limit_bytes"]
     
     while True:
-        result = _tracing_thread_drain_compressed_buffer(client, size_limit, size_limit_bytes)
+        result = _tracing_thread_drain_compressed_buffer(
+            client, size_limit, size_limit_bytes)
         if result is not None:
             time.sleep(0.150)  # Simulate call to backend
         else:
diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index a19640289..9e4c190ae 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -3,10 +3,10 @@
 import itertools
 import logging
 import uuid
-import io
-import zstandard
 from typing import Literal, Optional, Union, cast
 
+import zstandard
+
 from langsmith import schemas as ls_schemas
 from langsmith._internal import _orjson
 from langsmith._internal._multipart import MultipartPart, MultipartPartsAndContext
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index c6fb5714d..ea8350bd1 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -33,7 +33,6 @@
 import uuid
 import warnings
 import weakref
-import zstandard
 from inspect import signature
 from queue import PriorityQueue
 from typing import (
@@ -58,6 +57,7 @@
 from urllib import parse as urllib_parse
 
 import requests
+import zstandard
 from requests import adapters as requests_adapters
 from requests_toolbelt import (  # type: ignore[import-untyped]
     multipart as rqtb_multipart,
@@ -76,7 +76,9 @@
 )
 from langsmith._internal._background_thread import (
     tracing_control_thread_func as _tracing_control_thread_func,
-    tracing_control_thread_func_compress as _tracing_control_thread_func_compress
+)
+from langsmith._internal._background_thread import (
+    tracing_control_thread_func_compress as _tracing_control_thread_func_compress,
 )
 from langsmith._internal._beta_decorator import warn_beta
 from langsmith._internal._constants import (
@@ -92,11 +94,11 @@
     SerializedFeedbackOperation,
     SerializedRunOperation,
     combine_serialized_queue_operations,
+    compress_multipart_parts_and_context,
     serialize_feedback_dict,
     serialize_run_dict,
     serialized_feedback_operation_to_multipart_parts_and_context,
     serialized_run_operation_to_multipart_parts_and_context,
-    compress_multipart_parts_and_context,
 )
 from langsmith._internal._serde import dumps_json as _dumps_json
 

From 46c87408f89339ddb2cd6d65604d37a7598cf43f Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 17:58:41 -0800
Subject: [PATCH 08/56] fix mypy

---
 python/langsmith/_internal/_background_thread.py |  2 +-
 python/langsmith/_internal/_operations.py        |  2 +-
 python/langsmith/client.py                       | 13 ++++++-------
 3 files changed, 8 insertions(+), 9 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 5e986ac9e..0a1d36c61 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -238,7 +238,7 @@ def tracing_control_thread_func_compress(client_ref: weakref.ref[Client]) -> Non
         return
     batch_ingest_config = _ensure_ingest_config(client.info)
     size_limit: int = batch_ingest_config["size_limit"]
-    size_limit_bytes: int = batch_ingest_config["size_limit_bytes"]
+    size_limit_bytes: int | None = batch_ingest_config["size_limit_bytes"]
     
     while True:
         result = _tracing_thread_drain_compressed_buffer(
diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index 9e4c190ae..a6afaa1a0 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -277,7 +277,7 @@ def serialized_run_operation_to_multipart_parts_and_context(
 
 def compress_multipart_parts_and_context(
     parts_and_context: MultipartPartsAndContext, 
-    compressor_writer: zstandard.ZstdCompressorWriter,
+    compressor_writer: zstandard.ZstdCompressionWriter,
     boundary: str
 ) -> None:
     for part_name, (filename, data, content_type, headers) in parts_and_context.parts:
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index ea8350bd1..ddc389223 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -397,7 +397,6 @@ class Client:
         "boundary",
         "compressor",
         "compressor_writer",
-        "tracing_queue",
         "_run_count",
         "_buffer_lock",
     ]
@@ -504,12 +503,12 @@ def __init__(
         self.compress_traces = os.getenv("LANGSMITH_COMPRESS_TRACES") == "true"
         if self.compress_traces:
             self.boundary = BOUNDARY
-            self.compressor = zstandard.ZstdCompressor()
-            self.compressor_writer = self.compressor.stream_writer(
+            self.compressor: zstandard.ZstdCompressor = zstandard.ZstdCompressor()
+            self.tracing_queue: io.BytesIO = io.BytesIO()
+            self.compressor_writer: zstandard.ZstdCompressionWriter = self.compressor.stream_writer(
                 self.tracing_queue, closefd=False)
-            self.tracing_queue = io.BytesIO()
-            self._buffer_lock = threading.Lock()
-            self._run_count = 0
+            self._buffer_lock: threading.Lock = threading.Lock()
+            self._run_count: int = 0
             
         self._info = (
             info
@@ -1321,7 +1320,7 @@ def create_run(
             elif self.tracing_queue is not None:
                 serialized_op = serialize_run_dict("post", run_create)
                 if self.compress_traces:
-                    multipart_form = self.serialized_run_operation_to_multipart_parts_and_context(
+                    multipart_form = serialized_run_operation_to_multipart_parts_and_context(
                         serialized_op)
                     with self._buffer_lock:
                         compress_multipart_parts_and_context(

From a5cba8d968a5d3070e1bfbbe405257a6557968e5 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 18:08:32 -0800
Subject: [PATCH 09/56] implement correct timeouts

---
 .../langsmith/_internal/_background_thread.py | 40 +++++++++++++++----
 1 file changed, 33 insertions(+), 7 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 0a1d36c61..0805859e6 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -240,13 +240,39 @@ def tracing_control_thread_func_compress(client_ref: weakref.ref[Client]) -> Non
     size_limit: int = batch_ingest_config["size_limit"]
     size_limit_bytes: int | None = batch_ingest_config["size_limit_bytes"]
     
-    while True:
-        result = _tracing_thread_drain_compressed_buffer(
-            client, size_limit, size_limit_bytes)
-        if result is not None:
-            time.sleep(0.150)  # Simulate call to backend
-        else:
-            time.sleep(0.1)  # Avoid busy-waiting if no data ready
+    def keep_thread_active() -> bool:
+        # if `client.cleanup()` was called, stop thread
+        if not client or (
+            hasattr(client, "_manual_cleanup")
+            and client._manual_cleanup
+        ):
+            return False
+        if not threading.main_thread().is_alive():
+            # main thread is dead. should not be active
+            return False
+        return True
+
+    while keep_thread_active():
+        try:
+            result = _tracing_thread_drain_compressed_buffer(
+                client, size_limit, size_limit_bytes)
+            if result is not None:
+                # Simulating backend call
+                time.sleep(0.25)
+            else:
+                time.sleep(0.05)
+        except Exception:
+            logger.error("Error in tracing compression thread", exc_info=True)
+            time.sleep(0.1)  # Wait before retrying on error
+
+    # Drain the buffer on exit
+    try:
+        final_result = _tracing_thread_drain_compressed_buffer(
+            client, size_limit=1, size_limit_bytes=1)  # Force final drain
+        if final_result is not None:
+            time.sleep(0.25)  # backend call simulation
+    except Exception:
+        logger.error("Error in final buffer drain", exc_info=True)
 
 
 

From c32cb0cecb417f81e18372af23b6dfcb2ebf8375 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 19:16:09 -0800
Subject: [PATCH 10/56] stream instead of read data from buffer

---
 .../langsmith/_internal/_background_thread.py | 32 ++++++++++++-------
 1 file changed, 21 insertions(+), 11 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 0805859e6..d0a385f5a 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -10,6 +10,7 @@
 from queue import Empty, Queue
 from typing import (
     TYPE_CHECKING,
+    Iterable,
     List,
     Optional,
     Union,
@@ -94,10 +95,10 @@ def _tracing_thread_drain_queue(
 
 
 def _tracing_thread_drain_compressed_buffer(
-    client: Client,
+    client: "Client",
     size_limit: int = 100,
     size_limit_bytes: int = 50 * 1024 * 1024
-) -> Optional[bytes]:
+) -> Optional[Iterable[bytes]]:
     with client._buffer_lock:
         current_size = client.tracing_queue.tell()
 
@@ -111,7 +112,14 @@ def _tracing_thread_drain_compressed_buffer(
         client.compressor_writer.close()
 
         client.tracing_queue.seek(0)
-        data = client.tracing_queue.getvalue()
+
+        def data_stream() -> Iterable[bytes]:
+            chunk_size = 65536
+            while True:
+                chunk = client.tracing_queue.read(chunk_size)
+                if not chunk:
+                    break
+                yield chunk
 
         # Reinitialize for next batch
         client.tracing_queue = io.BytesIO()
@@ -119,7 +127,8 @@ def _tracing_thread_drain_compressed_buffer(
         client.compressor_writer = client.compressor.stream_writer(
             client.tracing_queue, closefd=False)
         client._run_count = 0
-        return data
+
+        return data_stream()
 
 def _tracing_thread_handle_batch(
     client: Client,
@@ -254,11 +263,11 @@ def keep_thread_active() -> bool:
 
     while keep_thread_active():
         try:
-            result = _tracing_thread_drain_compressed_buffer(
+            data_stream = _tracing_thread_drain_compressed_buffer(
                 client, size_limit, size_limit_bytes)
-            if result is not None:
-                # Simulating backend call
-                time.sleep(0.25)
+            if data_stream is not None:
+                for chunk in data_stream:
+                    time.sleep(0.150)  # Backend call simulation
             else:
                 time.sleep(0.05)
         except Exception:
@@ -267,10 +276,11 @@ def keep_thread_active() -> bool:
 
     # Drain the buffer on exit
     try:
-        final_result = _tracing_thread_drain_compressed_buffer(
+        final_data_stream = _tracing_thread_drain_compressed_buffer(
             client, size_limit=1, size_limit_bytes=1)  # Force final drain
-        if final_result is not None:
-            time.sleep(0.25)  # backend call simulation
+        if final_data_stream is not None:
+            for chunk in final_data_stream:
+                time.sleep(0.150)  # Final backend calls
     except Exception:
         logger.error("Error in final buffer drain", exc_info=True)
 

From 2aafc203da66523ffc3ca8f8f6631145c3089a5a Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 19:21:40 -0800
Subject: [PATCH 11/56] fix client type

---
 python/langsmith/_internal/_background_thread.py | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index d0a385f5a..8ad31a0a5 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -95,7 +95,7 @@ def _tracing_thread_drain_queue(
 
 
 def _tracing_thread_drain_compressed_buffer(
-    client: "Client",
+    client: Client,
     size_limit: int = 100,
     size_limit_bytes: int = 50 * 1024 * 1024
 ) -> Optional[Iterable[bytes]]:

From 03e4e0209d2bc30f6ee41aadaa1e40058c98f5ee Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 22:28:50 -0800
Subject: [PATCH 12/56] separate compressed buffer from tracing queue

---
 .../langsmith/_internal/_background_thread.py | 14 ++++---
 python/langsmith/client.py                    | 37 ++++++++++---------
 2 files changed, 28 insertions(+), 23 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 8ad31a0a5..932c80ec9 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -100,7 +100,7 @@ def _tracing_thread_drain_compressed_buffer(
     size_limit_bytes: int = 50 * 1024 * 1024
 ) -> Optional[Iterable[bytes]]:
     with client._buffer_lock:
-        current_size = client.tracing_queue.tell()
+        current_size = client.compressed_runs_buffer.tell()
 
         # Check if we should send now
         if not (client._run_count >= size_limit or current_size >= size_limit_bytes):
@@ -111,21 +111,21 @@ def _tracing_thread_drain_compressed_buffer(
         client.compressor_writer.flush()
         client.compressor_writer.close()
 
-        client.tracing_queue.seek(0)
+        client.compressed_runs_buffer.seek(0)
 
         def data_stream() -> Iterable[bytes]:
             chunk_size = 65536
             while True:
-                chunk = client.tracing_queue.read(chunk_size)
+                chunk = client.compressed_runs_buffer.read(chunk_size)
                 if not chunk:
                     break
                 yield chunk
 
         # Reinitialize for next batch
-        client.tracing_queue = io.BytesIO()
+        client.compressed_runs_buffer = io.BytesIO()
         client.compressor = zstd.ZstdCompressor()
         client.compressor_writer = client.compressor.stream_writer(
-            client.tracing_queue, closefd=False)
+            client.compressed_runs_buffer, closefd=False)
         client._run_count = 0
 
         return data_stream()
@@ -247,7 +247,9 @@ def tracing_control_thread_func_compress(client_ref: weakref.ref[Client]) -> Non
         return
     batch_ingest_config = _ensure_ingest_config(client.info)
     size_limit: int = batch_ingest_config["size_limit"]
-    size_limit_bytes: int | None = batch_ingest_config["size_limit_bytes"]
+    size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 50 * 1024 * 1024)
+    assert size_limit_bytes is not None
+
     
     def keep_thread_active() -> bool:
         # if `client.cleanup()` was called, stop thread
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index ddc389223..7be479953 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -399,6 +399,7 @@ class Client:
         "compressor_writer",
         "_run_count",
         "_buffer_lock",
+        "compressed_runs_buffer",
     ]
 
     def __init__(
@@ -504,9 +505,9 @@ def __init__(
         if self.compress_traces:
             self.boundary = BOUNDARY
             self.compressor: zstandard.ZstdCompressor = zstandard.ZstdCompressor()
-            self.tracing_queue: io.BytesIO = io.BytesIO()
+            self.compressed_runs_buffer: io.BytesIO = io.BytesIO()
             self.compressor_writer: zstandard.ZstdCompressionWriter = self.compressor.stream_writer(
-                self.tracing_queue, closefd=False)
+                self.compressed_runs_buffer, closefd=False)
             self._buffer_lock: threading.Lock = threading.Lock()
             self._run_count: int = 0
             
@@ -1317,19 +1318,19 @@ def create_run(
         ):
             if self._pyo3_client is not None:
                 self._pyo3_client.create_run(run_create)
+            if self.compressed_runs_buffer is not None:
+                serialized_op = serialize_run_dict("post", run_create)
+                multipart_form = serialized_run_operation_to_multipart_parts_and_context(
+                    serialized_op)
+                with self._buffer_lock:
+                    compress_multipart_parts_and_context(
+                        multipart_form, self.compressor_writer, self.boundary)
+                    self._run_count += 1
             elif self.tracing_queue is not None:
                 serialized_op = serialize_run_dict("post", run_create)
-                if self.compress_traces:
-                    multipart_form = serialized_run_operation_to_multipart_parts_and_context(
-                        serialized_op)
-                    with self._buffer_lock:
-                        compress_multipart_parts_and_context(
-                            multipart_form, self.compressor_writer, self.boundary)
-                        self._run_count += 1
-                else:
-                    self.tracing_queue.put(
-                        TracingQueueItem(run_create["dotted_order"], serialized_op)
-                    )
+                self.tracing_queue.put(
+                    TracingQueueItem(run_create["dotted_order"], serialized_op)
+                )
             else:
                 # Neither Rust nor Python batch ingestion is configured,
                 # fall back to the non-batch approach.
@@ -1766,6 +1767,7 @@ def update_run(
             data["attachments"] = attachments
         use_multipart = (
             self.tracing_queue is not None
+            or self.compressed_runs_buffer is not None
             # batch ingest requires trace_id and dotted_order to be set
             and data["trace_id"] is not None
             and data["dotted_order"] is not None
@@ -1788,19 +1790,20 @@ def update_run(
             data["events"] = events
         if data["extra"]:
             self._insert_runtime_env([data])
-        if use_multipart and self.tracing_queue is not None:
-            # not collecting attachments currently, use empty dict
+        if use_multipart:
             serialized_op = serialize_run_dict(operation="patch", payload=data)
-            if self.compress_traces:
+            if self.compressed_runs_buffer is not None:
                 multipart_form = serialized_run_operation_to_multipart_parts_and_context(serialized_op)
                 with self._buffer_lock:
                     compress_multipart_parts_and_context(
                         multipart_form, self.compressor_writer, self.boundary)
                     self._run_count += 1
-            else:
+            elif self.tracing_queue is not None:
                 self.tracing_queue.put(
                     TracingQueueItem(data["dotted_order"], serialized_op)
                 )
+            else:
+                self._update_run(data)
         else:
             self._update_run(data)
 

From c95253632ed6f6fbef5a67bb5e89ac62136edc10 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Mon, 9 Dec 2024 22:30:13 -0800
Subject: [PATCH 13/56] clean up update multipart

---
 python/langsmith/client.py | 29 +++++++++++++++--------------
 1 file changed, 15 insertions(+), 14 deletions(-)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 7be479953..86fc1f01b 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -1790,20 +1790,21 @@ def update_run(
             data["events"] = events
         if data["extra"]:
             self._insert_runtime_env([data])
-        if use_multipart:
-            serialized_op = serialize_run_dict(operation="patch", payload=data)
-            if self.compressed_runs_buffer is not None:
-                multipart_form = serialized_run_operation_to_multipart_parts_and_context(serialized_op)
-                with self._buffer_lock:
-                    compress_multipart_parts_and_context(
-                        multipart_form, self.compressor_writer, self.boundary)
-                    self._run_count += 1
-            elif self.tracing_queue is not None:
-                self.tracing_queue.put(
-                    TracingQueueItem(data["dotted_order"], serialized_op)
-                )
-            else:
-                self._update_run(data)
+        if not use_multipart:
+            self._update_run(data)
+            return
+
+        serialized_op = serialize_run_dict(operation="patch", payload=data)
+        if self.compressed_runs_buffer is not None:
+            multipart_form = serialized_run_operation_to_multipart_parts_and_context(serialized_op)
+            with self._buffer_lock:
+                compress_multipart_parts_and_context(
+                    multipart_form, self.compressor_writer, self.boundary)
+                self._run_count += 1
+        elif self.tracing_queue is not None:
+            self.tracing_queue.put(
+                TracingQueueItem(data["dotted_order"], serialized_op)
+            )
         else:
             self._update_run(data)
 

From c3fdd361624dce82242324566a97bee7f798f209 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Tue, 10 Dec 2024 09:54:36 -0800
Subject: [PATCH 14/56] address comments

---
 .../langsmith/_internal/_background_thread.py | 24 +++++++++----------
 python/langsmith/_internal/_operations.py     |  4 ++--
 python/langsmith/client.py                    |  7 +++---
 3 files changed, 17 insertions(+), 18 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 932c80ec9..ef74f7393 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -111,24 +111,24 @@ def _tracing_thread_drain_compressed_buffer(
         client.compressor_writer.flush()
         client.compressor_writer.close()
 
-        client.compressed_runs_buffer.seek(0)
-
-        def data_stream() -> Iterable[bytes]:
-            chunk_size = 65536
-            while True:
-                chunk = client.compressed_runs_buffer.read(chunk_size)
-                if not chunk:
-                    break
-                yield chunk
+        filled_buffer = client.compressed_runs_buffer
 
         # Reinitialize for next batch
         client.compressed_runs_buffer = io.BytesIO()
-        client.compressor = zstd.ZstdCompressor()
-        client.compressor_writer = client.compressor.stream_writer(
+        client.compressor_writer = zstd.ZstdCompressor(level=3).stream_writer(
             client.compressed_runs_buffer, closefd=False)
         client._run_count = 0
 
-        return data_stream()
+    filled_buffer.seek(0)
+    def data_stream() -> Iterable[bytes]:
+        chunk_size = 65536
+        while True:
+            chunk = filled_buffer.read(chunk_size)
+            if not chunk:
+                break
+            yield chunk
+
+    return data_stream()
 
 def _tracing_thread_handle_batch(
     client: Client,
diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index a6afaa1a0..f3325063c 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -5,7 +5,7 @@
 import uuid
 from typing import Literal, Optional, Union, cast
 
-import zstandard
+import zstandard as zstd
 
 from langsmith import schemas as ls_schemas
 from langsmith._internal import _orjson
@@ -277,7 +277,7 @@ def serialized_run_operation_to_multipart_parts_and_context(
 
 def compress_multipart_parts_and_context(
     parts_and_context: MultipartPartsAndContext, 
-    compressor_writer: zstandard.ZstdCompressionWriter,
+    compressor_writer: zstd.ZstdCompressionWriter,
     boundary: str
 ) -> None:
     for part_name, (filename, data, content_type, headers) in parts_and_context.parts:
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 86fc1f01b..a409c873d 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -57,7 +57,7 @@
 from urllib import parse as urllib_parse
 
 import requests
-import zstandard
+import zstandard as zstd
 from requests import adapters as requests_adapters
 from requests_toolbelt import (  # type: ignore[import-untyped]
     multipart as rqtb_multipart,
@@ -501,12 +501,11 @@ def __init__(
         # Create a session and register a finalizer to close it
         session_ = session if session else requests.Session()
         self.session = session_
-        self.compress_traces = os.getenv("LANGSMITH_COMPRESS_TRACES") == "true"
+        self.compress_traces = ls_utils.get_env_var("USE_RUN_COMPRESSION")
         if self.compress_traces:
             self.boundary = BOUNDARY
-            self.compressor: zstandard.ZstdCompressor = zstandard.ZstdCompressor()
             self.compressed_runs_buffer: io.BytesIO = io.BytesIO()
-            self.compressor_writer: zstandard.ZstdCompressionWriter = self.compressor.stream_writer(
+            self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor().stream_writer(
                 self.compressed_runs_buffer, closefd=False)
             self._buffer_lock: threading.Lock = threading.Lock()
             self._run_count: int = 0

From d6b186d22cb4accfc8f2738956a1b186eb65d247 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Tue, 10 Dec 2024 10:35:02 -0800
Subject: [PATCH 15/56] just write directly to compressor instead of streaming

---
 python/langsmith/_internal/_operations.py | 6 +-----
 1 file changed, 1 insertion(+), 5 deletions(-)

diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index f3325063c..23f8e443d 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -296,11 +296,7 @@ def compress_multipart_parts_and_context(
         compressor_writer.write(part_header.encode())
         
         if isinstance(data, (bytes, bytearray)):
-            with memoryview(data) as view:
-                chunk_size = 1024 * 1024  # 1MB chunks
-                for i in range(0, len(view), chunk_size):
-                    chunk = view[i:i + chunk_size]
-                    compressor_writer.write(chunk)
+            compressor_writer.write(data)
         else:
             compressor_writer.write(str(data).encode())
         

From f061c0b93dba99f9fecf0fcf929423e9602a303c Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Tue, 10 Dec 2024 11:12:59 -0800
Subject: [PATCH 16/56] set trcing queue to none

---
 python/langsmith/client.py | 3 +++
 1 file changed, 3 insertions(+)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index a409c873d..80d21ac48 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -509,6 +509,8 @@ def __init__(
                 self.compressed_runs_buffer, closefd=False)
             self._buffer_lock: threading.Lock = threading.Lock()
             self._run_count: int = 0
+        else:
+            self.compressed_runs_buffer = None
             
         self._info = (
             info
@@ -519,6 +521,7 @@ def __init__(
         atexit.register(close_session, session_)
         # Initialize auto batching
         if auto_batch_tracing and self.compress_traces:
+            self.tracing_queue = None
             threading.Thread(
                 target=_tracing_control_thread_func_compress,
                 # arg must be a weakref to self to avoid the Thread object

From 8a0a60e43555390f7b90a172f641bef6c6294498 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Tue, 10 Dec 2024 14:43:55 -0800
Subject: [PATCH 17/56] send multipart req

---
 .../langsmith/_internal/_background_thread.py |  6 +--
 python/langsmith/client.py                    | 50 +++++++++++++++++++
 2 files changed, 52 insertions(+), 4 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index ef74f7393..7ac4a14fe 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -268,8 +268,7 @@ def keep_thread_active() -> bool:
             data_stream = _tracing_thread_drain_compressed_buffer(
                 client, size_limit, size_limit_bytes)
             if data_stream is not None:
-                for chunk in data_stream:
-                    time.sleep(0.150)  # Backend call simulation
+                client._send_compressed_multipart_req(data_stream)
             else:
                 time.sleep(0.05)
         except Exception:
@@ -281,8 +280,7 @@ def keep_thread_active() -> bool:
         final_data_stream = _tracing_thread_drain_compressed_buffer(
             client, size_limit=1, size_limit_bytes=1)  # Force final drain
         if final_data_stream is not None:
-            for chunk in final_data_stream:
-                time.sleep(0.150)  # Final backend calls
+            client._send_compressed_multipart_req(final_data_stream)
     except Exception:
         logger.error("Error in final buffer drain", exc_info=True)
 
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 80d21ac48..50eb72852 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -1665,6 +1665,7 @@ def multipart_ingest(
     def _send_multipart_req(self, acc: MultipartPartsAndContext, *, attempts: int = 3):
         parts = acc.parts
         _context = acc.context
+        print(f"Sending multipart request with context: {_context}")
         for api_url, api_key in self._write_api_urls.items():
             for idx in range(1, attempts + 1):
                 try:
@@ -1708,6 +1709,55 @@ def _send_multipart_req(self, acc: MultipartPartsAndContext, *, attempts: int =
                         logger.warning(f"Failed to multipart ingest runs: {repr(e)}")
                     # do not retry by default
                     return
+                    
+        
+    def _send_compressed_multipart_req(self, data_stream, *, attempts: int = 3):
+        """Send a zstd-compressed multipart form data stream to the backend using similar retry logic
+        as _send_multipart_req."""
+
+        _context = {}
+        
+        for api_url, api_key in self._write_api_urls.items():
+            for idx in range(1, attempts + 1):
+                try:
+                    headers = {
+                        **self._headers,
+                        "X-API-KEY": api_key,
+                        "Content-Type": f"multipart/form-data; boundary={self.boundary}",
+                        "Content-Encoding": "zstd",
+                    }
+
+                    self.request_with_retries(
+                        "POST",
+                        f"{api_url}/runs/multipart",
+                        request_kwargs={
+                            "data": data_stream,
+                            "headers": headers,
+                        },
+                        stop_after_attempt=1,
+                        _context=_context,
+                    )
+                    break
+                except ls_utils.LangSmithConflictError:
+                    break
+                except (
+                    ls_utils.LangSmithConnectionError,
+                    ls_utils.LangSmithRequestTimeout,
+                    ls_utils.LangSmithAPIError,
+                ) as exc:
+                    if idx == attempts:
+                        logger.warning(f"Failed to send compressed multipart ingest: {exc}")
+                    else:
+                        continue
+                except Exception as e:
+                    try:
+                        exc_desc_lines = traceback.format_exception_only(type(e), e)
+                        exc_desc = "".join(exc_desc_lines).rstrip()
+                        logger.warning(f"Failed to send compressed multipart ingest: {exc_desc}")
+                    except Exception:
+                        logger.warning(f"Failed to send compressed multipart ingest: {repr(e)}")
+                    # Do not retry by default after unknown exceptions
+                    return
 
     def update_run(
         self,

From b2113ba10cafd11cb10a84dfeafb831c3b8267e5 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Tue, 10 Dec 2024 16:55:45 -0800
Subject: [PATCH 18/56] remove flush

---
 python/langsmith/_internal/_background_thread.py | 1 -
 1 file changed, 1 deletion(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 7ac4a14fe..f3c378895 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -108,7 +108,6 @@ def _tracing_thread_drain_compressed_buffer(
 
         # Write final boundary and close compression stream
         client.compressor_writer.write(f'--{client.boundary}--\r\n'.encode())
-        client.compressor_writer.flush()
         client.compressor_writer.close()
 
         filled_buffer = client.compressed_runs_buffer

From 982429a2408f836a7ddc67b039ee7e7afa0d692d Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Tue, 10 Dec 2024 16:57:20 -0800
Subject: [PATCH 19/56] remove print

---
 python/langsmith/client.py | 1 -
 1 file changed, 1 deletion(-)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 50eb72852..c2a106851 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -1665,7 +1665,6 @@ def multipart_ingest(
     def _send_multipart_req(self, acc: MultipartPartsAndContext, *, attempts: int = 3):
         parts = acc.parts
         _context = acc.context
-        print(f"Sending multipart request with context: {_context}")
         for api_url, api_key in self._write_api_urls.items():
             for idx in range(1, attempts + 1):
                 try:

From 5b58940b180509c70910f119a94c93a79d5f0789 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Tue, 10 Dec 2024 17:04:33 -0800
Subject: [PATCH 20/56] set compression level

---
 python/langsmith/client.py | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index c2a106851..acd442715 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -505,7 +505,7 @@ def __init__(
         if self.compress_traces:
             self.boundary = BOUNDARY
             self.compressed_runs_buffer: io.BytesIO = io.BytesIO()
-            self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor().stream_writer(
+            self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(level=3).stream_writer(
                 self.compressed_runs_buffer, closefd=False)
             self._buffer_lock: threading.Lock = threading.Lock()
             self._run_count: int = 0

From f2e5ed98f992402c8f146c097a5de8286bbcd6d9 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Tue, 10 Dec 2024 17:07:19 -0800
Subject: [PATCH 21/56] remove prints

---
 python/langsmith/_internal/_background_thread.py | 2 --
 1 file changed, 2 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index f3c378895..d700db018 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -102,7 +102,6 @@ def _tracing_thread_drain_compressed_buffer(
     with client._buffer_lock:
         current_size = client.compressed_runs_buffer.tell()
 
-        # Check if we should send now
         if not (client._run_count >= size_limit or current_size >= size_limit_bytes):
             return None
 
@@ -112,7 +111,6 @@ def _tracing_thread_drain_compressed_buffer(
 
         filled_buffer = client.compressed_runs_buffer
 
-        # Reinitialize for next batch
         client.compressed_runs_buffer = io.BytesIO()
         client.compressor_writer = zstd.ZstdCompressor(level=3).stream_writer(
             client.compressed_runs_buffer, closefd=False)

From e7dc6bcfbe40571952bd0caf194ac225a289b18c Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Tue, 10 Dec 2024 17:17:54 -0800
Subject: [PATCH 22/56] pass buffer directly to request

---
 python/langsmith/_internal/_background_thread.py | 12 ++----------
 1 file changed, 2 insertions(+), 10 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index d700db018..ebe51d358 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -98,7 +98,7 @@ def _tracing_thread_drain_compressed_buffer(
     client: Client,
     size_limit: int = 100,
     size_limit_bytes: int = 50 * 1024 * 1024
-) -> Optional[Iterable[bytes]]:
+) -> Optional[bytes]:
     with client._buffer_lock:
         current_size = client.compressed_runs_buffer.tell()
 
@@ -117,15 +117,7 @@ def _tracing_thread_drain_compressed_buffer(
         client._run_count = 0
 
     filled_buffer.seek(0)
-    def data_stream() -> Iterable[bytes]:
-        chunk_size = 65536
-        while True:
-            chunk = filled_buffer.read(chunk_size)
-            if not chunk:
-                break
-            yield chunk
-
-    return data_stream()
+    return filled_buffer
 
 def _tracing_thread_handle_batch(
     client: Client,

From fb8fa96b9a680e64e9763f77ae8c8b7ab041c8b3 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 11 Dec 2024 08:34:50 -0800
Subject: [PATCH 23/56] lint

---
 python/langsmith/_internal/_background_thread.py | 1 -
 python/langsmith/client.py                       | 5 +++--
 2 files changed, 3 insertions(+), 3 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index ebe51d358..eb05fd849 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -10,7 +10,6 @@
 from queue import Empty, Queue
 from typing import (
     TYPE_CHECKING,
-    Iterable,
     List,
     Optional,
     Union,
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index eebdd7945..e8e7f5386 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -1712,9 +1712,10 @@ def _send_multipart_req(self, acc: MultipartPartsAndContext, *, attempts: int =
                     
         
     def _send_compressed_multipart_req(self, data_stream, *, attempts: int = 3):
-        """Send a zstd-compressed multipart form data stream to the backend using similar retry logic
-        as _send_multipart_req."""
+        """Send a zstd-compressed multipart form data stream to the backend.
 
+        Uses similar retry logic as _send_multipart_req.
+        """
         _context = {}
         
         for api_url, api_key in self._write_api_urls.items():

From 9d0a4ec7ab4d2085874d76ced8e358dba525a366 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 11 Dec 2024 09:01:23 -0800
Subject: [PATCH 24/56] my fixes

---
 python/langsmith/_internal/_background_thread.py | 4 +++-
 python/langsmith/client.py                       | 8 ++++----
 2 files changed, 7 insertions(+), 5 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index eb05fd849..d9d21ce36 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -97,7 +97,9 @@ def _tracing_thread_drain_compressed_buffer(
     client: Client,
     size_limit: int = 100,
     size_limit_bytes: int = 50 * 1024 * 1024
-) -> Optional[bytes]:
+) -> Optional[io.BytesIO]:
+    assert client.compressed_runs_buffer is not None
+    assert client.compressor_writer is not None
     with client._buffer_lock:
         current_size = client.compressed_runs_buffer.tell()
 
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index e8e7f5386..7fa1df534 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -506,7 +506,7 @@ def __init__(
         self.compress_traces = ls_utils.get_env_var("USE_RUN_COMPRESSION")
         if self.compress_traces:
             self.boundary = BOUNDARY
-            self.compressed_runs_buffer: io.BytesIO = io.BytesIO()
+            self.compressed_runs_buffer: Optional[io.BytesIO] = io.BytesIO()
             self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(level=3).stream_writer(
                 self.compressed_runs_buffer, closefd=False)
             self._buffer_lock: threading.Lock = threading.Lock()
@@ -523,7 +523,7 @@ def __init__(
         atexit.register(close_session, session_)
         # Initialize auto batching
         if auto_batch_tracing and self.compress_traces:
-            self.tracing_queue = None
+            self.tracing_queue: Optional[PriorityQueue] = None
             threading.Thread(
                 target=_tracing_control_thread_func_compress,
                 # arg must be a weakref to self to avoid the Thread object
@@ -531,7 +531,7 @@ def __init__(
                 args=(weakref.ref(self),),
             ).start()
         elif auto_batch_tracing:
-            self.tracing_queue: Optional[PriorityQueue] = PriorityQueue()
+            self.tracing_queue = PriorityQueue()
 
             threading.Thread(
                 target=_tracing_control_thread_func,
@@ -1716,7 +1716,7 @@ def _send_compressed_multipart_req(self, data_stream, *, attempts: int = 3):
 
         Uses similar retry logic as _send_multipart_req.
         """
-        _context = {}
+        _context: str = ""
         
         for api_url, api_key in self._write_api_urls.items():
             for idx in range(1, attempts + 1):

From f3e79711941d8dc747e015a3af6d90c669b05361 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 11 Dec 2024 09:07:54 -0800
Subject: [PATCH 25/56] black reformatting

---
 .../langsmith/_internal/_background_thread.py | 22 +++++-----
 python/langsmith/_internal/_operations.py     | 26 +++++------
 python/langsmith/client.py                    | 43 +++++++++++++------
 3 files changed, 53 insertions(+), 38 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index d9d21ce36..25155ccf9 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -94,9 +94,7 @@ def _tracing_thread_drain_queue(
 
 
 def _tracing_thread_drain_compressed_buffer(
-    client: Client,
-    size_limit: int = 100,
-    size_limit_bytes: int = 50 * 1024 * 1024
+    client: Client, size_limit: int = 100, size_limit_bytes: int = 50 * 1024 * 1024
 ) -> Optional[io.BytesIO]:
     assert client.compressed_runs_buffer is not None
     assert client.compressor_writer is not None
@@ -107,19 +105,21 @@ def _tracing_thread_drain_compressed_buffer(
             return None
 
         # Write final boundary and close compression stream
-        client.compressor_writer.write(f'--{client.boundary}--\r\n'.encode())
+        client.compressor_writer.write(f"--{client.boundary}--\r\n".encode())
         client.compressor_writer.close()
 
         filled_buffer = client.compressed_runs_buffer
 
         client.compressed_runs_buffer = io.BytesIO()
         client.compressor_writer = zstd.ZstdCompressor(level=3).stream_writer(
-            client.compressed_runs_buffer, closefd=False)
+            client.compressed_runs_buffer, closefd=False
+        )
         client._run_count = 0
 
     filled_buffer.seek(0)
     return filled_buffer
 
+
 def _tracing_thread_handle_batch(
     client: Client,
     tracing_queue: Queue,
@@ -231,6 +231,7 @@ def keep_thread_active() -> bool:
     ):
         _tracing_thread_handle_batch(client, tracing_queue, next_batch, use_multipart)
 
+
 def tracing_control_thread_func_compress(client_ref: weakref.ref[Client]) -> None:
     client = client_ref()
     if client is None:
@@ -240,12 +241,10 @@ def tracing_control_thread_func_compress(client_ref: weakref.ref[Client]) -> Non
     size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 50 * 1024 * 1024)
     assert size_limit_bytes is not None
 
-    
     def keep_thread_active() -> bool:
         # if `client.cleanup()` was called, stop thread
         if not client or (
-            hasattr(client, "_manual_cleanup")
-            and client._manual_cleanup
+            hasattr(client, "_manual_cleanup") and client._manual_cleanup
         ):
             return False
         if not threading.main_thread().is_alive():
@@ -256,7 +255,8 @@ def keep_thread_active() -> bool:
     while keep_thread_active():
         try:
             data_stream = _tracing_thread_drain_compressed_buffer(
-                client, size_limit, size_limit_bytes)
+                client, size_limit, size_limit_bytes
+            )
             if data_stream is not None:
                 client._send_compressed_multipart_req(data_stream)
             else:
@@ -268,14 +268,14 @@ def keep_thread_active() -> bool:
     # Drain the buffer on exit
     try:
         final_data_stream = _tracing_thread_drain_compressed_buffer(
-            client, size_limit=1, size_limit_bytes=1)  # Force final drain
+            client, size_limit=1, size_limit_bytes=1
+        )  # Force final drain
         if final_data_stream is not None:
             client._send_compressed_multipart_req(final_data_stream)
     except Exception:
         logger.error("Error in final buffer drain", exc_info=True)
 
 
-
 def _tracing_sub_thread_func(
     client_ref: weakref.ref[Client],
     use_multipart: bool,
diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index 23f8e443d..fca108796 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -276,29 +276,29 @@ def serialized_run_operation_to_multipart_parts_and_context(
 
 
 def compress_multipart_parts_and_context(
-    parts_and_context: MultipartPartsAndContext, 
+    parts_and_context: MultipartPartsAndContext,
     compressor_writer: zstd.ZstdCompressionWriter,
-    boundary: str
+    boundary: str,
 ) -> None:
     for part_name, (filename, data, content_type, headers) in parts_and_context.parts:
-        part_header = f'--{boundary}\r\n'
+        part_header = f"--{boundary}\r\n"
         part_header += f'Content-Disposition: form-data; name="{part_name}"'
-        
+
         if filename:
             part_header += f'; filename="{filename}"'
-        
-        part_header += f'\r\nContent-Type: {content_type}\r\n'
-        
+
+        part_header += f"\r\nContent-Type: {content_type}\r\n"
+
         for header_name, header_value in headers.items():
-            part_header += f'{header_name}: {header_value}\r\n'
-        
-        part_header += '\r\n'
+            part_header += f"{header_name}: {header_value}\r\n"
+
+        part_header += "\r\n"
         compressor_writer.write(part_header.encode())
-        
+
         if isinstance(data, (bytes, bytearray)):
             compressor_writer.write(data)
         else:
             compressor_writer.write(str(data).encode())
-        
+
         # Write part terminator
-        compressor_writer.write(b'\r\n')
+        compressor_writer.write(b"\r\n")
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 7fa1df534..100912e18 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -507,13 +507,14 @@ def __init__(
         if self.compress_traces:
             self.boundary = BOUNDARY
             self.compressed_runs_buffer: Optional[io.BytesIO] = io.BytesIO()
-            self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(level=3).stream_writer(
-                self.compressed_runs_buffer, closefd=False)
+            self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(
+                level=3
+            ).stream_writer(self.compressed_runs_buffer, closefd=False)
             self._buffer_lock: threading.Lock = threading.Lock()
             self._run_count: int = 0
         else:
             self.compressed_runs_buffer = None
-            
+
         self._info = (
             info
             if info is None or isinstance(info, ls_schemas.LangSmithInfo)
@@ -1323,11 +1324,15 @@ def create_run(
                 self._pyo3_client.create_run(run_create)
             if self.compressed_runs_buffer is not None:
                 serialized_op = serialize_run_dict("post", run_create)
-                multipart_form = serialized_run_operation_to_multipart_parts_and_context(
-                    serialized_op)
+                multipart_form = (
+                    serialized_run_operation_to_multipart_parts_and_context(
+                        serialized_op
+                    )
+                )
                 with self._buffer_lock:
                     compress_multipart_parts_and_context(
-                        multipart_form, self.compressor_writer, self.boundary)
+                        multipart_form, self.compressor_writer, self.boundary
+                    )
                     self._run_count += 1
             elif self.tracing_queue is not None:
                 serialized_op = serialize_run_dict("post", run_create)
@@ -1709,15 +1714,14 @@ def _send_multipart_req(self, acc: MultipartPartsAndContext, *, attempts: int =
                         logger.warning(f"Failed to multipart ingest runs: {repr(e)}")
                     # do not retry by default
                     return
-                    
-        
+
     def _send_compressed_multipart_req(self, data_stream, *, attempts: int = 3):
         """Send a zstd-compressed multipart form data stream to the backend.
 
         Uses similar retry logic as _send_multipart_req.
         """
         _context: str = ""
-        
+
         for api_url, api_key in self._write_api_urls.items():
             for idx in range(1, attempts + 1):
                 try:
@@ -1747,16 +1751,22 @@ def _send_compressed_multipart_req(self, data_stream, *, attempts: int = 3):
                     ls_utils.LangSmithAPIError,
                 ) as exc:
                     if idx == attempts:
-                        logger.warning(f"Failed to send compressed multipart ingest: {exc}")
+                        logger.warning(
+                            f"Failed to send compressed multipart ingest: {exc}"
+                        )
                     else:
                         continue
                 except Exception as e:
                     try:
                         exc_desc_lines = traceback.format_exception_only(type(e), e)
                         exc_desc = "".join(exc_desc_lines).rstrip()
-                        logger.warning(f"Failed to send compressed multipart ingest: {exc_desc}")
+                        logger.warning(
+                            f"Failed to send compressed multipart ingest: {exc_desc}"
+                        )
                     except Exception:
-                        logger.warning(f"Failed to send compressed multipart ingest: {repr(e)}")
+                        logger.warning(
+                            f"Failed to send compressed multipart ingest: {repr(e)}"
+                        )
                     # Do not retry by default after unknown exceptions
                     return
 
@@ -1847,10 +1857,15 @@ def update_run(
         elif use_multipart:
             serialized_op = serialize_run_dict(operation="patch", payload=data)
             if self.compressed_runs_buffer is not None:
-                multipart_form = serialized_run_operation_to_multipart_parts_and_context(serialized_op)
+                multipart_form = (
+                    serialized_run_operation_to_multipart_parts_and_context(
+                        serialized_op
+                    )
+                )
                 with self._buffer_lock:
                     compress_multipart_parts_and_context(
-                        multipart_form, self.compressor_writer, self.boundary)
+                        multipart_form, self.compressor_writer, self.boundary
+                    )
                     self._run_count += 1
             elif self.tracing_queue is not None:
                 self.tracing_queue.put(

From 066b9b6a2448b33619f51f696c0c46b6db21898b Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 11 Dec 2024 13:34:36 -0800
Subject: [PATCH 26/56] multithreaded compression

---
 python/langsmith/_internal/_background_thread.py | 2 +-
 python/langsmith/client.py                       | 2 +-
 2 files changed, 2 insertions(+), 2 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 25155ccf9..499ed79bc 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -111,7 +111,7 @@ def _tracing_thread_drain_compressed_buffer(
         filled_buffer = client.compressed_runs_buffer
 
         client.compressed_runs_buffer = io.BytesIO()
-        client.compressor_writer = zstd.ZstdCompressor(level=3).stream_writer(
+        client.compressor_writer = zstd.ZstdCompressor(level=3, threads=-1).stream_writer(
             client.compressed_runs_buffer, closefd=False
         )
         client._run_count = 0
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 100912e18..89e2c9858 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -508,7 +508,7 @@ def __init__(
             self.boundary = BOUNDARY
             self.compressed_runs_buffer: Optional[io.BytesIO] = io.BytesIO()
             self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(
-                level=3
+                level=3, threads=-1
             ).stream_writer(self.compressed_runs_buffer, closefd=False)
             self._buffer_lock: threading.Lock = threading.Lock()
             self._run_count: int = 0

From ec1566041d65d50f491154f7c5d6f1b66da2344c Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 11 Dec 2024 16:33:47 -0800
Subject: [PATCH 27/56] add parallel works for sending multipart req

---
 .../langsmith/_internal/_background_thread.py | 52 ++++++++++++++++---
 python/langsmith/client.py                    |  9 ++--
 2 files changed, 47 insertions(+), 14 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 499ed79bc..2b80220c6 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -17,7 +17,7 @@
 )
 
 import zstandard as zstd
-
+import os
 from langsmith import schemas as ls_schemas
 from langsmith._internal._constants import (
     _AUTO_SCALE_DOWN_NEMPTY_TRIGGER,
@@ -94,7 +94,7 @@ def _tracing_thread_drain_queue(
 
 
 def _tracing_thread_drain_compressed_buffer(
-    client: Client, size_limit: int = 100, size_limit_bytes: int = 50 * 1024 * 1024
+    client: Client, size_limit: int = 100, size_limit_bytes: int = 65_536
 ) -> Optional[io.BytesIO]:
     assert client.compressed_runs_buffer is not None
     assert client.compressor_writer is not None
@@ -155,7 +155,7 @@ def _ensure_ingest_config(
 ) -> ls_schemas.BatchIngestConfig:
     default_config = ls_schemas.BatchIngestConfig(
         use_multipart_endpoint=False,
-        size_limit_bytes=50 * 1024 * 1024,
+        size_limit_bytes=None,  # Note this field is not used here
         size_limit=100,
         scale_up_nthreads_limit=_AUTO_SCALE_UP_NTHREADS_LIMIT,
         scale_up_qsize_trigger=_AUTO_SCALE_UP_QSIZE_TRIGGER,
@@ -231,16 +231,44 @@ def keep_thread_active() -> bool:
     ):
         _tracing_thread_handle_batch(client, tracing_queue, next_batch, use_multipart)
 
+def _worker_thread_func(client: Client, request_queue: Queue) -> None:
+    """Worker thread function that processes requests from the queue"""
+    while True:
+        try:
+            data_stream = request_queue.get()
+            
+            if data_stream is None:
+                break
+            
+            client._send_compressed_multipart_req(data_stream)
+            
+        except Exception:
+            logger.error("Error in worker thread processing request", exc_info=True)
+        finally:
+            request_queue.task_done()
 
-def tracing_control_thread_func_compress(client_ref: weakref.ref[Client]) -> None:
+def tracing_control_thread_func_compress_parallel(client_ref: weakref.ref[Client]) -> None:
     client = client_ref()
     if client is None:
         return
+
     batch_ingest_config = _ensure_ingest_config(client.info)
     size_limit: int = batch_ingest_config["size_limit"]
-    size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 50 * 1024 * 1024)
+    size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 65_536)
     assert size_limit_bytes is not None
 
+    num_workers = min(4, os.cpu_count())
+    request_queue: Queue = Queue(maxsize=num_workers * 2)
+    workers = []
+    
+    for _ in range(num_workers):
+        worker = threading.Thread(
+            target=_worker_thread_func,
+            args=(client, request_queue),
+        )
+        worker.start()
+        workers.append(worker)
+
     def keep_thread_active() -> bool:
         # if `client.cleanup()` was called, stop thread
         if not client or (
@@ -258,7 +286,7 @@ def keep_thread_active() -> bool:
                 client, size_limit, size_limit_bytes
             )
             if data_stream is not None:
-                client._send_compressed_multipart_req(data_stream)
+                request_queue.put(data_stream)
             else:
                 time.sleep(0.05)
         except Exception:
@@ -271,9 +299,17 @@ def keep_thread_active() -> bool:
             client, size_limit=1, size_limit_bytes=1
         )  # Force final drain
         if final_data_stream is not None:
-            client._send_compressed_multipart_req(final_data_stream)
+            request_queue.put(final_data_stream)
+
+        request_queue.join()
+
+        for _ in workers:
+            request_queue.put(None)
+        for worker in workers:
+            worker.join()
+
     except Exception:
-        logger.error("Error in final buffer drain", exc_info=True)
+        logger.error("Error in final cleanup", exc_info=True)
 
 
 def _tracing_sub_thread_func(
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 89e2c9858..a72dedf3c 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -79,7 +79,7 @@
     tracing_control_thread_func as _tracing_control_thread_func,
 )
 from langsmith._internal._background_thread import (
-    tracing_control_thread_func_compress as _tracing_control_thread_func_compress,
+    tracing_control_thread_func_compress_parallel as _tracing_control_thread_func_compress_parallel,
 )
 from langsmith._internal._beta_decorator import warn_beta
 from langsmith._internal._constants import (
@@ -526,7 +526,7 @@ def __init__(
         if auto_batch_tracing and self.compress_traces:
             self.tracing_queue: Optional[PriorityQueue] = None
             threading.Thread(
-                target=_tracing_control_thread_func_compress,
+                target=_tracing_control_thread_func_compress_parallel,
                 # arg must be a weakref to self to avoid the Thread object
                 # preventing garbage collection of the Client object
                 args=(weakref.ref(self),),
@@ -1716,10 +1716,7 @@ def _send_multipart_req(self, acc: MultipartPartsAndContext, *, attempts: int =
                     return
 
     def _send_compressed_multipart_req(self, data_stream, *, attempts: int = 3):
-        """Send a zstd-compressed multipart form data stream to the backend.
-
-        Uses similar retry logic as _send_multipart_req.
-        """
+        """Send a zstd-compressed multipart form data stream to the backend."""
         _context: str = ""
 
         for api_url, api_key in self._write_api_urls.items():

From 35e9843f64e6c235136150258de51e5a8a8e46ee Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 11 Dec 2024 16:55:17 -0800
Subject: [PATCH 28/56] reformatting

---
 python/langsmith/_internal/_background_thread.py | 11 +++++++----
 1 file changed, 7 insertions(+), 4 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 2b80220c6..a856df557 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -3,6 +3,7 @@
 import functools
 import io
 import logging
+import os
 import sys
 import threading
 import time
@@ -17,7 +18,7 @@
 )
 
 import zstandard as zstd
-import os
+
 from langsmith import schemas as ls_schemas
 from langsmith._internal._constants import (
     _AUTO_SCALE_DOWN_NEMPTY_TRIGGER,
@@ -111,7 +112,9 @@ def _tracing_thread_drain_compressed_buffer(
         filled_buffer = client.compressed_runs_buffer
 
         client.compressed_runs_buffer = io.BytesIO()
-        client.compressor_writer = zstd.ZstdCompressor(level=3, threads=-1).stream_writer(
+        client.compressor_writer = zstd.ZstdCompressor(
+            level=3, threads=-1
+        ).stream_writer(
             client.compressed_runs_buffer, closefd=False
         )
         client._run_count = 0
@@ -232,7 +235,6 @@ def keep_thread_active() -> bool:
         _tracing_thread_handle_batch(client, tracing_queue, next_batch, use_multipart)
 
 def _worker_thread_func(client: Client, request_queue: Queue) -> None:
-    """Worker thread function that processes requests from the queue"""
     while True:
         try:
             data_stream = request_queue.get()
@@ -247,7 +249,8 @@ def _worker_thread_func(client: Client, request_queue: Queue) -> None:
         finally:
             request_queue.task_done()
 
-def tracing_control_thread_func_compress_parallel(client_ref: weakref.ref[Client]) -> None:
+def tracing_control_thread_func_compress_parallel(client_ref: weakref.ref[Client]
+                                                  ) -> None:
     client = client_ref()
     if client is None:
         return

From 59b5f27d4e66ee6297067cf62946c68139bca1f4 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 11 Dec 2024 16:55:32 -0800
Subject: [PATCH 29/56] black reformat

---
 .../langsmith/_internal/_background_thread.py | 19 ++++++++++---------
 1 file changed, 10 insertions(+), 9 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index a856df557..2e8c599d3 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -114,9 +114,7 @@ def _tracing_thread_drain_compressed_buffer(
         client.compressed_runs_buffer = io.BytesIO()
         client.compressor_writer = zstd.ZstdCompressor(
             level=3, threads=-1
-        ).stream_writer(
-            client.compressed_runs_buffer, closefd=False
-        )
+        ).stream_writer(client.compressed_runs_buffer, closefd=False)
         client._run_count = 0
 
     filled_buffer.seek(0)
@@ -234,23 +232,26 @@ def keep_thread_active() -> bool:
     ):
         _tracing_thread_handle_batch(client, tracing_queue, next_batch, use_multipart)
 
+
 def _worker_thread_func(client: Client, request_queue: Queue) -> None:
     while True:
         try:
             data_stream = request_queue.get()
-            
+
             if data_stream is None:
                 break
-            
+
             client._send_compressed_multipart_req(data_stream)
-            
+
         except Exception:
             logger.error("Error in worker thread processing request", exc_info=True)
         finally:
             request_queue.task_done()
 
-def tracing_control_thread_func_compress_parallel(client_ref: weakref.ref[Client]
-                                                  ) -> None:
+
+def tracing_control_thread_func_compress_parallel(
+    client_ref: weakref.ref[Client],
+) -> None:
     client = client_ref()
     if client is None:
         return
@@ -263,7 +264,7 @@ def tracing_control_thread_func_compress_parallel(client_ref: weakref.ref[Client
     num_workers = min(4, os.cpu_count())
     request_queue: Queue = Queue(maxsize=num_workers * 2)
     workers = []
-    
+
     for _ in range(num_workers):
         worker = threading.Thread(
             target=_worker_thread_func,

From ce44b253d4344ce523018cc0b5a6f61f2a43f972 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 11 Dec 2024 16:58:44 -0800
Subject: [PATCH 30/56] mypy

---
 python/langsmith/_internal/_background_thread.py | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 2e8c599d3..8e967d63e 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -261,7 +261,7 @@ def tracing_control_thread_func_compress_parallel(
     size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 65_536)
     assert size_limit_bytes is not None
 
-    num_workers = min(4, os.cpu_count())
+    num_workers = min(4, os.cpu_count() or 1)
     request_queue: Queue = Queue(maxsize=num_workers * 2)
     workers = []
 

From 181f83960e68c2651c47dbab883165d2f3ff582c Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 12 Dec 2024 10:29:04 -0800
Subject: [PATCH 31/56] increase payload size to 20mb

---
 python/langsmith/_internal/_background_thread.py | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 8e967d63e..54013c7a6 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -95,7 +95,7 @@ def _tracing_thread_drain_queue(
 
 
 def _tracing_thread_drain_compressed_buffer(
-    client: Client, size_limit: int = 100, size_limit_bytes: int = 65_536
+    client: Client, size_limit: int = 100, size_limit_bytes: int = 20_971_520
 ) -> Optional[io.BytesIO]:
     assert client.compressed_runs_buffer is not None
     assert client.compressor_writer is not None
@@ -258,7 +258,7 @@ def tracing_control_thread_func_compress_parallel(
 
     batch_ingest_config = _ensure_ingest_config(client.info)
     size_limit: int = batch_ingest_config["size_limit"]
-    size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 65_536)
+    size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 20_971_520)
     assert size_limit_bytes is not None
 
     num_workers = min(4, os.cpu_count() or 1)

From 0120dce1b0935b9abb69e3e3004c60cd126af2d9 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 12 Dec 2024 10:50:46 -0800
Subject: [PATCH 32/56] use multipart

---
 python/langsmith/client.py | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index a72dedf3c..391f2be74 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -1824,8 +1824,8 @@ def update_run(
         if attachments:
             data["attachments"] = attachments
         use_multipart = (
-            self.tracing_queue is not None
-            or self.compressed_runs_buffer is not None
+            (self.tracing_queue is not None
+            or self.compressed_runs_buffer is not None)
             # batch ingest requires trace_id and dotted_order to be set
             and data["trace_id"] is not None
             and data["dotted_order"] is not None

From e2ada65f8b6e4dba6fbfc4ff5480e77d40adfd16 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 12 Dec 2024 14:26:02 -0800
Subject: [PATCH 33/56] use threadpoolexecutor

---
 .../langsmith/_internal/_background_thread.py | 56 +++++++------------
 1 file changed, 19 insertions(+), 37 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 54013c7a6..6b8bbdcd7 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -8,6 +8,8 @@
 import threading
 import time
 import weakref
+from multiprocessing import cpu_count
+import concurrent.futures
 from queue import Empty, Queue
 from typing import (
     TYPE_CHECKING,
@@ -36,6 +38,7 @@
 
 logger = logging.getLogger("langsmith.client")
 
+HTTP_REQUEST_THREAD_POOL = concurrent.futures.ThreadPoolExecutor(max_workers=cpu_count())
 
 @functools.total_ordering
 class TracingQueueItem:
@@ -233,22 +236,6 @@ def keep_thread_active() -> bool:
         _tracing_thread_handle_batch(client, tracing_queue, next_batch, use_multipart)
 
 
-def _worker_thread_func(client: Client, request_queue: Queue) -> None:
-    while True:
-        try:
-            data_stream = request_queue.get()
-
-            if data_stream is None:
-                break
-
-            client._send_compressed_multipart_req(data_stream)
-
-        except Exception:
-            logger.error("Error in worker thread processing request", exc_info=True)
-        finally:
-            request_queue.task_done()
-
-
 def tracing_control_thread_func_compress_parallel(
     client_ref: weakref.ref[Client],
 ) -> None:
@@ -261,18 +248,6 @@ def tracing_control_thread_func_compress_parallel(
     size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 20_971_520)
     assert size_limit_bytes is not None
 
-    num_workers = min(4, os.cpu_count() or 1)
-    request_queue: Queue = Queue(maxsize=num_workers * 2)
-    workers = []
-
-    for _ in range(num_workers):
-        worker = threading.Thread(
-            target=_worker_thread_func,
-            args=(client, request_queue),
-        )
-        worker.start()
-        workers.append(worker)
-
     def keep_thread_active() -> bool:
         # if `client.cleanup()` was called, stop thread
         if not client or (
@@ -290,7 +265,13 @@ def keep_thread_active() -> bool:
                 client, size_limit, size_limit_bytes
             )
             if data_stream is not None:
-                request_queue.put(data_stream)
+                try:
+                    HTTP_REQUEST_THREAD_POOL.submit(
+                        client._send_compressed_multipart_req, data_stream
+                    )
+                    print("submitted request")
+                except RuntimeError:
+                    client._send_compressed_multipart_req(data_stream)
             else:
                 time.sleep(0.05)
         except Exception:
@@ -303,15 +284,16 @@ def keep_thread_active() -> bool:
             client, size_limit=1, size_limit_bytes=1
         )  # Force final drain
         if final_data_stream is not None:
-            request_queue.put(final_data_stream)
-
-        request_queue.join()
-
-        for _ in workers:
-            request_queue.put(None)
-        for worker in workers:
-            worker.join()
+            try:
+                concurrent.futures.wait(
+                    HTTP_REQUEST_THREAD_POOL.submit(
+                        client._send_compressed_multipart_req, final_data_stream
+                    )
+                )
+            except RuntimeError:
+                client._send_compressed_multipart_req(final_data_stream)
 
+        
     except Exception:
         logger.error("Error in final cleanup", exc_info=True)
 

From 25f4f19aa3ad5ebea11da8c95e1140a6ca181bb8 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 12 Dec 2024 15:41:00 -0800
Subject: [PATCH 34/56] fix thread garbage collection

---
 python/langsmith/_internal/_background_thread.py | 16 ++++++++++++++--
 1 file changed, 14 insertions(+), 2 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 6b8bbdcd7..31513272a 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -247,6 +247,7 @@ def tracing_control_thread_func_compress_parallel(
     size_limit: int = batch_ingest_config["size_limit"]
     size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 20_971_520)
     assert size_limit_bytes is not None
+    num_known_refs = 3
 
     def keep_thread_active() -> bool:
         # if `client.cleanup()` was called, stop thread
@@ -257,7 +258,19 @@ def keep_thread_active() -> bool:
         if not threading.main_thread().is_alive():
             # main thread is dead. should not be active
             return False
-        return True
+        if hasattr(sys, "getrefcount"):
+            # check if client refs count indicates we're the only remaining
+            # reference to the client
+            
+            # Count active threads
+            thread_pool = HTTP_REQUEST_THREAD_POOL._threads
+            active_count = sum(1 for thread in thread_pool if thread is not None and thread.is_alive())
+
+            return sys.getrefcount(client) > num_known_refs + active_count
+        else:
+            # in PyPy, there is no sys.getrefcount attribute
+            # for now, keep thread alive
+            return True
 
     while keep_thread_active():
         try:
@@ -269,7 +282,6 @@ def keep_thread_active() -> bool:
                     HTTP_REQUEST_THREAD_POOL.submit(
                         client._send_compressed_multipart_req, data_stream
                     )
-                    print("submitted request")
                 except RuntimeError:
                     client._send_compressed_multipart_req(data_stream)
             else:

From 5b0cca4fffc563958d1208f0c91fabaac0327cd9 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 12 Dec 2024 15:49:40 -0800
Subject: [PATCH 35/56] add flush method

---
 python/langsmith/client.py | 39 ++++++++++++++++++++++++++++++++++++++
 1 file changed, 39 insertions(+)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 391f2be74..14f18ae9e 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -1887,6 +1887,45 @@ def _update_run(self, run_update: dict) -> None:
                 },
             )
 
+
+    def flush_compressed_runs(self, attempts: int = 3) -> None:
+        """
+        Forcefully flush the currently buffered compressed runs.
+        """
+        if not self.compress_traces or self.compressed_runs_buffer is None:
+            return
+
+        # Attempt to drain and send any remaining data
+        from langsmith._internal._background_thread import _tracing_thread_drain_compressed_buffer, HTTP_REQUEST_THREAD_POOL
+
+        final_data_stream = _tracing_thread_drain_compressed_buffer(
+            self, size_limit=1, size_limit_bytes=1
+        )
+
+        if final_data_stream is not None:
+            # We have data to send
+            future = None
+            try:
+                future = HTTP_REQUEST_THREAD_POOL.submit(
+                    self._send_compressed_multipart_req, final_data_stream, attempts=attempts
+                )
+            except RuntimeError:
+                # In case the ThreadPoolExecutor is already shutdown
+                self._send_compressed_multipart_req(final_data_stream, attempts=attempts)
+
+            # If we got a future, wait for it to complete
+            if future is not None:
+                cf.wait([future])
+
+    def flush(self) -> None:
+        """
+        A convenience method to flush either queue or compressed buffer, depending on mode.
+        """
+        if self.compress_traces and self.compressed_runs_buffer is not None:
+            self.flush_compressed_runs()
+        elif self.tracing_queue is not None:
+            self.tracing_queue.join()
+
     def _load_child_runs(self, run: ls_schemas.Run) -> ls_schemas.Run:
         """Load child runs for a given run.
 

From f59f7be596ba9243f9e66543832dd6d9dfbf5c38 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 12 Dec 2024 15:52:43 -0800
Subject: [PATCH 36/56] return early

---
 python/langsmith/client.py | 28 +++++++++++++++-------------
 1 file changed, 15 insertions(+), 13 deletions(-)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 14f18ae9e..36b4c45da 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -1902,20 +1902,22 @@ def flush_compressed_runs(self, attempts: int = 3) -> None:
             self, size_limit=1, size_limit_bytes=1
         )
 
-        if final_data_stream is not None:
-            # We have data to send
-            future = None
-            try:
-                future = HTTP_REQUEST_THREAD_POOL.submit(
-                    self._send_compressed_multipart_req, final_data_stream, attempts=attempts
-                )
-            except RuntimeError:
-                # In case the ThreadPoolExecutor is already shutdown
-                self._send_compressed_multipart_req(final_data_stream, attempts=attempts)
+        if final_data_stream is None:
+            return
+
+        # We have data to send
+        future = None
+        try:
+            future = HTTP_REQUEST_THREAD_POOL.submit(
+                self._send_compressed_multipart_req, final_data_stream, attempts=attempts
+            )
+        except RuntimeError:
+            # In case the ThreadPoolExecutor is already shutdown
+            self._send_compressed_multipart_req(final_data_stream, attempts=attempts)
 
-            # If we got a future, wait for it to complete
-            if future is not None:
-                cf.wait([future])
+        # If we got a future, wait for it to complete
+        if future is not None:
+            cf.wait([future])
 
     def flush(self) -> None:
         """

From b76e662caa6a1b0f9402b9c3c741c51d16c12581 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 12 Dec 2024 16:00:29 -0800
Subject: [PATCH 37/56] lint

---
 .../langsmith/_internal/_background_thread.py | 15 +++++++------
 python/langsmith/client.py                    | 21 +++++++++----------
 2 files changed, 19 insertions(+), 17 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 31513272a..4964e4258 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -1,15 +1,14 @@
 from __future__ import annotations
 
+import concurrent.futures
 import functools
 import io
 import logging
-import os
 import sys
 import threading
 import time
 import weakref
 from multiprocessing import cpu_count
-import concurrent.futures
 from queue import Empty, Queue
 from typing import (
     TYPE_CHECKING,
@@ -38,7 +37,10 @@
 
 logger = logging.getLogger("langsmith.client")
 
-HTTP_REQUEST_THREAD_POOL = concurrent.futures.ThreadPoolExecutor(max_workers=cpu_count())
+HTTP_REQUEST_THREAD_POOL = concurrent.futures.ThreadPoolExecutor(
+    max_workers=cpu_count()
+)
+
 
 @functools.total_ordering
 class TracingQueueItem:
@@ -261,10 +263,12 @@ def keep_thread_active() -> bool:
         if hasattr(sys, "getrefcount"):
             # check if client refs count indicates we're the only remaining
             # reference to the client
-            
+
             # Count active threads
             thread_pool = HTTP_REQUEST_THREAD_POOL._threads
-            active_count = sum(1 for thread in thread_pool if thread is not None and thread.is_alive())
+            active_count = sum(
+                1 for thread in thread_pool if thread is not None and thread.is_alive()
+            )
 
             return sys.getrefcount(client) > num_known_refs + active_count
         else:
@@ -305,7 +309,6 @@ def keep_thread_active() -> bool:
             except RuntimeError:
                 client._send_compressed_multipart_req(final_data_stream)
 
-        
     except Exception:
         logger.error("Error in final cleanup", exc_info=True)
 
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 36b4c45da..e09c49b6d 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -1824,8 +1824,7 @@ def update_run(
         if attachments:
             data["attachments"] = attachments
         use_multipart = (
-            (self.tracing_queue is not None
-            or self.compressed_runs_buffer is not None)
+            (self.tracing_queue is not None or self.compressed_runs_buffer is not None)
             # batch ingest requires trace_id and dotted_order to be set
             and data["trace_id"] is not None
             and data["dotted_order"] is not None
@@ -1887,16 +1886,16 @@ def _update_run(self, run_update: dict) -> None:
                 },
             )
 
-
     def flush_compressed_runs(self, attempts: int = 3) -> None:
-        """
-        Forcefully flush the currently buffered compressed runs.
-        """
+        """Force flush the currently buffered compressed runs."""
         if not self.compress_traces or self.compressed_runs_buffer is None:
             return
 
         # Attempt to drain and send any remaining data
-        from langsmith._internal._background_thread import _tracing_thread_drain_compressed_buffer, HTTP_REQUEST_THREAD_POOL
+        from langsmith._internal._background_thread import (
+            HTTP_REQUEST_THREAD_POOL,
+            _tracing_thread_drain_compressed_buffer,
+        )
 
         final_data_stream = _tracing_thread_drain_compressed_buffer(
             self, size_limit=1, size_limit_bytes=1
@@ -1909,7 +1908,9 @@ def flush_compressed_runs(self, attempts: int = 3) -> None:
         future = None
         try:
             future = HTTP_REQUEST_THREAD_POOL.submit(
-                self._send_compressed_multipart_req, final_data_stream, attempts=attempts
+                self._send_compressed_multipart_req,
+                final_data_stream,
+                attempts=attempts,
             )
         except RuntimeError:
             # In case the ThreadPoolExecutor is already shutdown
@@ -1920,9 +1921,7 @@ def flush_compressed_runs(self, attempts: int = 3) -> None:
             cf.wait([future])
 
     def flush(self) -> None:
-        """
-        A convenience method to flush either queue or compressed buffer, depending on mode.
-        """
+        """Flush either queue or compressed buffer, depending on mode."""
         if self.compress_traces and self.compressed_runs_buffer is not None:
             self.flush_compressed_runs()
         elif self.tracing_queue is not None:

From efa4bd6520d7de1f3bb97cdbaddfb25fa63f8c3b Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 12 Dec 2024 16:04:11 -0800
Subject: [PATCH 38/56] wait

---
 python/langsmith/_internal/_background_thread.py | 8 +++++---
 1 file changed, 5 insertions(+), 3 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 4964e4258..61413b869 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -302,9 +302,11 @@ def keep_thread_active() -> bool:
         if final_data_stream is not None:
             try:
                 concurrent.futures.wait(
-                    HTTP_REQUEST_THREAD_POOL.submit(
-                        client._send_compressed_multipart_req, final_data_stream
-                    )
+                    [
+                        HTTP_REQUEST_THREAD_POOL.submit(
+                            client._send_compressed_multipart_req, final_data_stream
+                        )
+                    ]
                 )
             except RuntimeError:
                 client._send_compressed_multipart_req(final_data_stream)

From 0e06bde7e45769dc7d7c92b406043f6126587296 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Fri, 13 Dec 2024 11:25:37 -0800
Subject: [PATCH 39/56] signal bg threads data is available instead of sleeping

---
 .../langsmith/_internal/_background_thread.py | 37 ++++++++++---------
 python/langsmith/client.py                    |  4 ++
 2 files changed, 23 insertions(+), 18 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 61413b869..7a594980b 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -6,7 +6,6 @@
 import logging
 import sys
 import threading
-import time
 import weakref
 from multiprocessing import cpu_count
 from queue import Empty, Queue
@@ -276,23 +275,25 @@ def keep_thread_active() -> bool:
             # for now, keep thread alive
             return True
 
-    while keep_thread_active():
-        try:
-            data_stream = _tracing_thread_drain_compressed_buffer(
-                client, size_limit, size_limit_bytes
-            )
-            if data_stream is not None:
-                try:
-                    HTTP_REQUEST_THREAD_POOL.submit(
-                        client._send_compressed_multipart_req, data_stream
-                    )
-                except RuntimeError:
-                    client._send_compressed_multipart_req(data_stream)
-            else:
-                time.sleep(0.05)
-        except Exception:
-            logger.error("Error in tracing compression thread", exc_info=True)
-            time.sleep(0.1)  # Wait before retrying on error
+    while True:
+        triggered = client._data_available_event.wait(timeout=0.05)
+        if not keep_thread_active():
+            break
+        if not triggered:
+            continue
+        client._data_available_event.clear()
+
+        data_stream = _tracing_thread_drain_compressed_buffer(
+            client, size_limit, size_limit_bytes
+        )
+
+        if data_stream is not None:
+            try:
+                HTTP_REQUEST_THREAD_POOL.submit(
+                    client._send_compressed_multipart_req, data_stream
+                )
+            except RuntimeError:
+                client._send_compressed_multipart_req(data_stream)
 
     # Drain the buffer on exit
     try:
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index e09c49b6d..759fad1f2 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -402,6 +402,7 @@ class Client:
         "_run_count",
         "_buffer_lock",
         "compressed_runs_buffer",
+        "_data_available_event",
     ]
 
     def __init__(
@@ -511,6 +512,7 @@ def __init__(
                 level=3, threads=-1
             ).stream_writer(self.compressed_runs_buffer, closefd=False)
             self._buffer_lock: threading.Lock = threading.Lock()
+            self._data_available_event = threading.Event()
             self._run_count: int = 0
         else:
             self.compressed_runs_buffer = None
@@ -1334,6 +1336,7 @@ def create_run(
                         multipart_form, self.compressor_writer, self.boundary
                     )
                     self._run_count += 1
+                    self._data_available_event.set()
             elif self.tracing_queue is not None:
                 serialized_op = serialize_run_dict("post", run_create)
                 self.tracing_queue.put(
@@ -1863,6 +1866,7 @@ def update_run(
                         multipart_form, self.compressor_writer, self.boundary
                     )
                     self._run_count += 1
+                    self._data_available_event.set()
             elif self.tracing_queue is not None:
                 self.tracing_queue.put(
                     TracingQueueItem(data["dotted_order"], serialized_op)

From f997895a9724095b794bd72dfc0278147c861586 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Fri, 13 Dec 2024 11:41:16 -0800
Subject: [PATCH 40/56] improve buffer checks

---
 python/langsmith/_internal/_background_thread.py | 11 ++++++++++-
 1 file changed, 10 insertions(+), 1 deletion(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 7a594980b..fce8ee601 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -106,7 +106,16 @@ def _tracing_thread_drain_compressed_buffer(
     with client._buffer_lock:
         current_size = client.compressed_runs_buffer.tell()
 
-        if not (client._run_count >= size_limit or current_size >= size_limit_bytes):
+        if size_limit is not None and size_limit <= 0:
+            raise ValueError(f"size_limit must be positive; got {size_limit}")
+        if size_limit_bytes is not None and size_limit_bytes < 0:
+            raise ValueError(
+                f"size_limit_bytes must be nonnegative; got {size_limit_bytes}"
+            )
+
+        if (size_limit_bytes is None or current_size < size_limit_bytes) and (
+            size_limit is None or len(client._run_count) < size_limit
+        ):
             return None
 
         # Write final boundary and close compression stream

From fbc217f8a383598914e678deae6fae5872d38e34 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Fri, 13 Dec 2024 12:22:49 -0800
Subject: [PATCH 41/56] mypy

---
 python/langsmith/_internal/_background_thread.py | 5 ++---
 1 file changed, 2 insertions(+), 3 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index fce8ee601..8257ecf14 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -99,7 +99,7 @@ def _tracing_thread_drain_queue(
 
 
 def _tracing_thread_drain_compressed_buffer(
-    client: Client, size_limit: int = 100, size_limit_bytes: int = 20_971_520
+    client: Client, size_limit: int = 100, size_limit_bytes: int | None = 20_971_520
 ) -> Optional[io.BytesIO]:
     assert client.compressed_runs_buffer is not None
     assert client.compressor_writer is not None
@@ -114,7 +114,7 @@ def _tracing_thread_drain_compressed_buffer(
             )
 
         if (size_limit_bytes is None or current_size < size_limit_bytes) and (
-            size_limit is None or len(client._run_count) < size_limit
+            size_limit is None or client._run_count < size_limit
         ):
             return None
 
@@ -256,7 +256,6 @@ def tracing_control_thread_func_compress_parallel(
     batch_ingest_config = _ensure_ingest_config(client.info)
     size_limit: int = batch_ingest_config["size_limit"]
     size_limit_bytes = batch_ingest_config.get("size_limit_bytes", 20_971_520)
-    assert size_limit_bytes is not None
     num_known_refs = 3
 
     def keep_thread_active() -> bool:

From 7b6c201f59665359bc88ae16dec4e378a2631463 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 18 Dec 2024 14:06:43 -1000
Subject: [PATCH 42/56] Use more threads for backend requests

---
 python/langsmith/_internal/_background_thread.py | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 8257ecf14..33be46e57 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -37,7 +37,7 @@
 logger = logging.getLogger("langsmith.client")
 
 HTTP_REQUEST_THREAD_POOL = concurrent.futures.ThreadPoolExecutor(
-    max_workers=cpu_count()
+    max_workers=cpu_count()*3
 )
 
 

From 35d46edf070db7742960555d58b7904b235d8325 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Wed, 18 Dec 2024 14:25:47 -1000
Subject: [PATCH 43/56] fix futures waiting

---
 python/langsmith/_internal/_background_thread.py | 3 ++-
 python/langsmith/client.py                       | 9 +++++++--
 2 files changed, 9 insertions(+), 3 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 33be46e57..e2fdb2bda 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -297,9 +297,10 @@ def keep_thread_active() -> bool:
 
         if data_stream is not None:
             try:
-                HTTP_REQUEST_THREAD_POOL.submit(
+                future = HTTP_REQUEST_THREAD_POOL.submit(
                     client._send_compressed_multipart_req, data_stream
                 )
+                client._futures.add(future)
             except RuntimeError:
                 client._send_compressed_multipart_req(data_stream)
 
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 759fad1f2..d45919697 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -403,6 +403,7 @@ class Client:
         "_buffer_lock",
         "compressed_runs_buffer",
         "_data_available_event",
+        "_futures",
     ]
 
     def __init__(
@@ -506,6 +507,7 @@ def __init__(
         self.session = session_
         self.compress_traces = ls_utils.get_env_var("USE_RUN_COMPRESSION")
         if self.compress_traces:
+            self._futures: set[cf.Future] = set()
             self.boundary = BOUNDARY
             self.compressed_runs_buffer: Optional[io.BytesIO] = io.BytesIO()
             self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(
@@ -1916,13 +1918,16 @@ def flush_compressed_runs(self, attempts: int = 3) -> None:
                 final_data_stream,
                 attempts=attempts,
             )
+            self._futures.add(future)
         except RuntimeError:
             # In case the ThreadPoolExecutor is already shutdown
             self._send_compressed_multipart_req(final_data_stream, attempts=attempts)
 
         # If we got a future, wait for it to complete
-        if future is not None:
-            cf.wait([future])
+        if self._futures:
+            done, _ = cf.wait(self._futures, return_when=cf.ALL_COMPLETED)
+            # Remove completed futures
+            self._futures.difference_update(done)
 
     def flush(self) -> None:
         """Flush either queue or compressed buffer, depending on mode."""

From dbef2ec3afb47339830448db113769ea33682820 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 10:23:50 -0800
Subject: [PATCH 44/56] remove unused slot

---
 python/langsmith/_internal/_background_thread.py |  4 ++--
 python/langsmith/client.py                       | 11 +++++------
 2 files changed, 7 insertions(+), 8 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index e2fdb2bda..ae98101f8 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -37,7 +37,7 @@
 logger = logging.getLogger("langsmith.client")
 
 HTTP_REQUEST_THREAD_POOL = concurrent.futures.ThreadPoolExecutor(
-    max_workers=cpu_count()*3
+    max_workers=cpu_count() * 3
 )
 
 
@@ -119,7 +119,7 @@ def _tracing_thread_drain_compressed_buffer(
             return None
 
         # Write final boundary and close compression stream
-        client.compressor_writer.write(f"--{client.boundary}--\r\n".encode())
+        client.compressor_writer.write(f"--{client._boundary}--\r\n".encode())
         client.compressor_writer.close()
 
         filled_buffer = client.compressed_runs_buffer
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index d45919697..600f4d1aa 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -396,8 +396,7 @@ class Client:
         "_manual_cleanup",
         "_pyo3_client",
         "compress_traces",
-        "boundary",
-        "compressor",
+        "_boundary",
         "compressor_writer",
         "_run_count",
         "_buffer_lock",
@@ -508,7 +507,7 @@ def __init__(
         self.compress_traces = ls_utils.get_env_var("USE_RUN_COMPRESSION")
         if self.compress_traces:
             self._futures: set[cf.Future] = set()
-            self.boundary = BOUNDARY
+            self._boundary = BOUNDARY
             self.compressed_runs_buffer: Optional[io.BytesIO] = io.BytesIO()
             self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(
                 level=3, threads=-1
@@ -1335,7 +1334,7 @@ def create_run(
                 )
                 with self._buffer_lock:
                     compress_multipart_parts_and_context(
-                        multipart_form, self.compressor_writer, self.boundary
+                        multipart_form, self.compressor_writer, self._boundary
                     )
                     self._run_count += 1
                     self._data_available_event.set()
@@ -1730,7 +1729,7 @@ def _send_compressed_multipart_req(self, data_stream, *, attempts: int = 3):
                     headers = {
                         **self._headers,
                         "X-API-KEY": api_key,
-                        "Content-Type": f"multipart/form-data; boundary={self.boundary}",
+                        "Content-Type": f"multipart/form-data; boundary={self._boundary}",
                         "Content-Encoding": "zstd",
                     }
 
@@ -1865,7 +1864,7 @@ def update_run(
                 )
                 with self._buffer_lock:
                     compress_multipart_parts_and_context(
-                        multipart_form, self.compressor_writer, self.boundary
+                        multipart_form, self.compressor_writer, self._boundary
                     )
                     self._run_count += 1
                     self._data_available_event.set()

From 6fad59626d313d8918cc3d6655a5c6fc3eeec876 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 10:34:35 -0800
Subject: [PATCH 45/56] Flush background threads

---
 .../langsmith/_internal/_background_thread.py |  8 ++---
 python/langsmith/client.py                    | 32 +++++++++----------
 2 files changed, 19 insertions(+), 21 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index ae98101f8..6a3d715db 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -1,6 +1,6 @@
 from __future__ import annotations
 
-import concurrent.futures
+import concurrent.futures as cf
 import functools
 import io
 import logging
@@ -36,9 +36,7 @@
 
 logger = logging.getLogger("langsmith.client")
 
-HTTP_REQUEST_THREAD_POOL = concurrent.futures.ThreadPoolExecutor(
-    max_workers=cpu_count() * 3
-)
+HTTP_REQUEST_THREAD_POOL = cf.ThreadPoolExecutor(max_workers=cpu_count() * 3)
 
 
 @functools.total_ordering
@@ -311,7 +309,7 @@ def keep_thread_active() -> bool:
         )  # Force final drain
         if final_data_stream is not None:
             try:
-                concurrent.futures.wait(
+                cf.wait(
                     [
                         HTTP_REQUEST_THREAD_POOL.submit(
                             client._send_compressed_multipart_req, final_data_stream
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 600f4d1aa..02c31cccc 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -1906,25 +1906,25 @@ def flush_compressed_runs(self, attempts: int = 3) -> None:
             self, size_limit=1, size_limit_bytes=1
         )
 
-        if final_data_stream is None:
-            return
-
-        # We have data to send
-        future = None
-        try:
-            future = HTTP_REQUEST_THREAD_POOL.submit(
-                self._send_compressed_multipart_req,
-                final_data_stream,
-                attempts=attempts,
-            )
-            self._futures.add(future)
-        except RuntimeError:
-            # In case the ThreadPoolExecutor is already shutdown
-            self._send_compressed_multipart_req(final_data_stream, attempts=attempts)
+        if final_data_stream is not None:
+            # We have data to send
+            future = None
+            try:
+                future = HTTP_REQUEST_THREAD_POOL.submit(
+                    self._send_compressed_multipart_req,
+                    final_data_stream,
+                    attempts=attempts,
+                )
+                self._futures.add(future)
+            except RuntimeError:
+                # In case the ThreadPoolExecutor is already shutdown
+                self._send_compressed_multipart_req(
+                    final_data_stream, attempts=attempts
+                )
 
         # If we got a future, wait for it to complete
         if self._futures:
-            done, _ = cf.wait(self._futures, return_when=cf.ALL_COMPLETED)
+            done, _ = cf.wait(self._futures)
             # Remove completed futures
             self._futures.difference_update(done)
 

From 5cc947a90ae61e1ac2c8761fd59816e730659188 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 13:04:24 -0800
Subject: [PATCH 46/56] make boundary constant

---
 python/langsmith/_internal/_background_thread.py |  3 ++-
 python/langsmith/_internal/_constants.py         |  3 +++
 python/langsmith/client.py                       | 14 ++++++--------
 3 files changed, 11 insertions(+), 9 deletions(-)

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index 6a3d715db..e595c5b73 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -24,6 +24,7 @@
     _AUTO_SCALE_DOWN_NEMPTY_TRIGGER,
     _AUTO_SCALE_UP_NTHREADS_LIMIT,
     _AUTO_SCALE_UP_QSIZE_TRIGGER,
+    _BOUNDARY,
 )
 from langsmith._internal._operations import (
     SerializedFeedbackOperation,
@@ -117,7 +118,7 @@ def _tracing_thread_drain_compressed_buffer(
             return None
 
         # Write final boundary and close compression stream
-        client.compressor_writer.write(f"--{client._boundary}--\r\n".encode())
+        client.compressor_writer.write(f"--{_BOUNDARY}--\r\n".encode())
         client.compressor_writer.close()
 
         filled_buffer = client.compressed_runs_buffer
diff --git a/python/langsmith/_internal/_constants.py b/python/langsmith/_internal/_constants.py
index 1703d9e88..43505024f 100644
--- a/python/langsmith/_internal/_constants.py
+++ b/python/langsmith/_internal/_constants.py
@@ -1,5 +1,8 @@
+import uuid
+
 _SIZE_LIMIT_BYTES = 20_971_520  # 20MB by default
 _AUTO_SCALE_UP_QSIZE_TRIGGER = 200
 _AUTO_SCALE_UP_NTHREADS_LIMIT = 32
 _AUTO_SCALE_DOWN_NEMPTY_TRIGGER = 4
 _BLOCKSIZE_BYTES = 1024 * 1024  # 1MB
+_BOUNDARY = uuid.uuid4().hex
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 02c31cccc..576892943 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -86,6 +86,7 @@
     _AUTO_SCALE_UP_NTHREADS_LIMIT,
     _BLOCKSIZE_BYTES,
     _SIZE_LIMIT_BYTES,
+    _BOUNDARY,
 )
 from langsmith._internal._multipart import (
     MultipartPart,
@@ -141,7 +142,6 @@ class ZoneInfo:  # type: ignore[no-redef]
 X_API_KEY = "x-api-key"
 WARNED_ATTACHMENTS = False
 EMPTY_SEQ: tuple[Dict, ...] = ()
-BOUNDARY = uuid.uuid4().hex
 URLLIB3_SUPPORTS_BLOCKSIZE = "key_blocksize" in signature(PoolKey).parameters
 
 
@@ -396,7 +396,6 @@ class Client:
         "_manual_cleanup",
         "_pyo3_client",
         "compress_traces",
-        "_boundary",
         "compressor_writer",
         "_run_count",
         "_buffer_lock",
@@ -507,7 +506,6 @@ def __init__(
         self.compress_traces = ls_utils.get_env_var("USE_RUN_COMPRESSION")
         if self.compress_traces:
             self._futures: set[cf.Future] = set()
-            self._boundary = BOUNDARY
             self.compressed_runs_buffer: Optional[io.BytesIO] = io.BytesIO()
             self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(
                 level=3, threads=-1
@@ -1334,7 +1332,7 @@ def create_run(
                 )
                 with self._buffer_lock:
                     compress_multipart_parts_and_context(
-                        multipart_form, self.compressor_writer, self._boundary
+                        multipart_form, self.compressor_writer, _BOUNDARY
                     )
                     self._run_count += 1
                     self._data_available_event.set()
@@ -1678,7 +1676,7 @@ def _send_multipart_req(self, acc: MultipartPartsAndContext, *, attempts: int =
         for api_url, api_key in self._write_api_urls.items():
             for idx in range(1, attempts + 1):
                 try:
-                    encoder = rqtb_multipart.MultipartEncoder(parts, boundary=BOUNDARY)
+                    encoder = rqtb_multipart.MultipartEncoder(parts, boundary=_BOUNDARY)
                     if encoder.len <= 20_000_000:  # ~20 MB
                         data = encoder.to_string()
                     else:
@@ -1729,7 +1727,7 @@ def _send_compressed_multipart_req(self, data_stream, *, attempts: int = 3):
                     headers = {
                         **self._headers,
                         "X-API-KEY": api_key,
-                        "Content-Type": f"multipart/form-data; boundary={self._boundary}",
+                        "Content-Type": f"multipart/form-data; boundary={_BOUNDARY}",
                         "Content-Encoding": "zstd",
                     }
 
@@ -1864,7 +1862,7 @@ def update_run(
                 )
                 with self._buffer_lock:
                     compress_multipart_parts_and_context(
-                        multipart_form, self.compressor_writer, self._boundary
+                        multipart_form, self.compressor_writer, _BOUNDARY
                     )
                     self._run_count += 1
                     self._data_available_event.set()
@@ -3767,7 +3765,7 @@ def _prepare_multipart_data(
                     )
                 )
 
-        encoder = rqtb_multipart.MultipartEncoder(parts, boundary=BOUNDARY)
+        encoder = rqtb_multipart.MultipartEncoder(parts, boundary=_BOUNDARY)
         if encoder.len <= 20_000_000:  # ~20 MB
             data = encoder.to_string()
         else:

From d4b2aa4bb18011575ba81c15ba5deeb427d0ffdc Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 13:06:28 -0800
Subject: [PATCH 47/56] Remove slot for bool val

---
 python/langsmith/client.py | 10 ++++------
 1 file changed, 4 insertions(+), 6 deletions(-)

diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 576892943..0035308fd 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -395,7 +395,6 @@ class Client:
         "_settings",
         "_manual_cleanup",
         "_pyo3_client",
-        "compress_traces",
         "compressor_writer",
         "_run_count",
         "_buffer_lock",
@@ -503,8 +502,7 @@ def __init__(
         # Create a session and register a finalizer to close it
         session_ = session if session else requests.Session()
         self.session = session_
-        self.compress_traces = ls_utils.get_env_var("USE_RUN_COMPRESSION")
-        if self.compress_traces:
+        if self.ls_utils.get_env_var("USE_RUN_COMPRESSION"):
             self._futures: set[cf.Future] = set()
             self.compressed_runs_buffer: Optional[io.BytesIO] = io.BytesIO()
             self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(
@@ -524,7 +522,7 @@ def __init__(
         weakref.finalize(self, close_session, self.session)
         atexit.register(close_session, session_)
         # Initialize auto batching
-        if auto_batch_tracing and self.compress_traces:
+        if auto_batch_tracing and self.compressed_runs_buffer is not None:
             self.tracing_queue: Optional[PriorityQueue] = None
             threading.Thread(
                 target=_tracing_control_thread_func_compress_parallel,
@@ -1891,7 +1889,7 @@ def _update_run(self, run_update: dict) -> None:
 
     def flush_compressed_runs(self, attempts: int = 3) -> None:
         """Force flush the currently buffered compressed runs."""
-        if not self.compress_traces or self.compressed_runs_buffer is None:
+        if self.compressed_runs_buffer is None:
             return
 
         # Attempt to drain and send any remaining data
@@ -1928,7 +1926,7 @@ def flush_compressed_runs(self, attempts: int = 3) -> None:
 
     def flush(self) -> None:
         """Flush either queue or compressed buffer, depending on mode."""
-        if self.compress_traces and self.compressed_runs_buffer is not None:
+        if self.compressed_runs_buffer is not None:
             self.flush_compressed_runs()
         elif self.tracing_queue is not None:
             self.tracing_queue.join()

From 63e55f76364eec62e155cf4a8b0e3c42b295185d Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 13:08:14 -0800
Subject: [PATCH 48/56] Use a single join() rather than copying the header
 strings

---
 python/langsmith/_internal/_operations.py | 21 +++++++++++----------
 1 file changed, 11 insertions(+), 10 deletions(-)

diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index fca108796..f75411084 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -274,26 +274,27 @@ def serialized_run_operation_to_multipart_parts_and_context(
         f"trace={op.trace_id},id={op.id}",
     )
 
-
 def compress_multipart_parts_and_context(
     parts_and_context: MultipartPartsAndContext,
     compressor_writer: zstd.ZstdCompressionWriter,
     boundary: str,
 ) -> None:
     for part_name, (filename, data, content_type, headers) in parts_and_context.parts:
-        part_header = f"--{boundary}\r\n"
-        part_header += f'Content-Disposition: form-data; name="{part_name}"'
+        header_parts = [
+            f"--{boundary}\r\n",
+            f'Content-Disposition: form-data; name="{part_name}"'
+        ]
 
         if filename:
-            part_header += f'; filename="{filename}"'
-
-        part_header += f"\r\nContent-Type: {content_type}\r\n"
+            header_parts.append(f'; filename="{filename}"')
 
-        for header_name, header_value in headers.items():
-            part_header += f"{header_name}: {header_value}\r\n"
+        header_parts.extend([
+            f"\r\nContent-Type: {content_type}\r\n",
+            *[f"{k}: {v}\r\n" for k, v in headers.items()],
+            "\r\n"
+        ])
 
-        part_header += "\r\n"
-        compressor_writer.write(part_header.encode())
+        compressor_writer.write("".join(header_parts).encode())
 
         if isinstance(data, (bytes, bytearray)):
             compressor_writer.write(data)

From 874c748ad0e78fce20c6bc4ba6ad18bab2bb16a7 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 13:13:34 -0800
Subject: [PATCH 49/56] Add zstandard license

---
 python/docs/templates/zstandard/COPYRIGHT.txt | 27 +++++++++++++++++++
 1 file changed, 27 insertions(+)
 create mode 100644 python/docs/templates/zstandard/COPYRIGHT.txt

diff --git a/python/docs/templates/zstandard/COPYRIGHT.txt b/python/docs/templates/zstandard/COPYRIGHT.txt
new file mode 100644
index 000000000..912c1883e
--- /dev/null
+++ b/python/docs/templates/zstandard/COPYRIGHT.txt
@@ -0,0 +1,27 @@
+Copyright (c) 2016, Gregory Szorc
+All rights reserved.
+
+Redistribution and use in source and binary forms, with or without modification,
+are permitted provided that the following conditions are met:
+
+1. Redistributions of source code must retain the above copyright notice, this
+list of conditions and the following disclaimer.
+
+2. Redistributions in binary form must reproduce the above copyright notice,
+this list of conditions and the following disclaimer in the documentation
+and/or other materials provided with the distribution.
+
+3. Neither the name of the copyright holder nor the names of its contributors
+may be used to endorse or promote products derived from this software without
+specific prior written permission.
+
+THIS SOFTWARE IS PROVIDED BY THE COPYRIGHT HOLDERS AND CONTRIBUTORS "AS IS" AND
+ANY EXPRESS OR IMPLIED WARRANTIES, INCLUDING, BUT NOT LIMITED TO, THE IMPLIED
+WARRANTIES OF MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE ARE
+DISCLAIMED. IN NO EVENT SHALL THE COPYRIGHT HOLDER OR CONTRIBUTORS BE LIABLE FOR
+ANY DIRECT, INDIRECT, INCIDENTAL, SPECIAL, EXEMPLARY, OR CONSEQUENTIAL DAMAGES
+(INCLUDING, BUT NOT LIMITED TO, PROCUREMENT OF SUBSTITUTE GOODS OR SERVICES;
+LOSS OF USE, DATA, OR PROFITS; OR BUSINESS INTERRUPTION) HOWEVER CAUSED AND ON
+ANY THEORY OF LIABILITY, WHETHER IN CONTRACT, STRICT LIABILITY, OR TORT
+(INCLUDING NEGLIGENCE OR OTHERWISE) ARISING IN ANY WAY OUT OF THE USE OF THIS
+SOFTWARE, EVEN IF ADVISED OF THE POSSIBILITY OF SUCH DAMAGE.
\ No newline at end of file

From 0b3d6b8490b41ccb5ac6025d1d2d3cdfb2ef7fb0 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 17:06:23 -0800
Subject: [PATCH 50/56] lint

---
 python/langsmith/_internal/_operations.py | 15 +++++++++------
 python/langsmith/client.py                |  2 +-
 2 files changed, 10 insertions(+), 7 deletions(-)

diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index f75411084..904a20d3b 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -274,6 +274,7 @@ def serialized_run_operation_to_multipart_parts_and_context(
         f"trace={op.trace_id},id={op.id}",
     )
 
+
 def compress_multipart_parts_and_context(
     parts_and_context: MultipartPartsAndContext,
     compressor_writer: zstd.ZstdCompressionWriter,
@@ -282,17 +283,19 @@ def compress_multipart_parts_and_context(
     for part_name, (filename, data, content_type, headers) in parts_and_context.parts:
         header_parts = [
             f"--{boundary}\r\n",
-            f'Content-Disposition: form-data; name="{part_name}"'
+            f'Content-Disposition: form-data; name="{part_name}"',
         ]
 
         if filename:
             header_parts.append(f'; filename="{filename}"')
 
-        header_parts.extend([
-            f"\r\nContent-Type: {content_type}\r\n",
-            *[f"{k}: {v}\r\n" for k, v in headers.items()],
-            "\r\n"
-        ])
+        header_parts.extend(
+            [
+                f"\r\nContent-Type: {content_type}\r\n",
+                *[f"{k}: {v}\r\n" for k, v in headers.items()],
+                "\r\n",
+            ]
+        )
 
         compressor_writer.write("".join(header_parts).encode())
 
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index 0035308fd..a273cf8e2 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -85,8 +85,8 @@
 from langsmith._internal._constants import (
     _AUTO_SCALE_UP_NTHREADS_LIMIT,
     _BLOCKSIZE_BYTES,
-    _SIZE_LIMIT_BYTES,
     _BOUNDARY,
+    _SIZE_LIMIT_BYTES,
 )
 from langsmith._internal._multipart import (
     MultipartPart,

From 773993945ca05e48b1c9bb785ef0d4e45c639734 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 17:34:50 -0800
Subject: [PATCH 51/56] Create compressed runs object

---
 .../langsmith/_internal/_background_thread.py | 23 ++++------
 .../langsmith/_internal/_compressed_runs.py   | 21 +++++++++
 python/langsmith/client.py                    | 46 +++++++++----------
 3 files changed, 50 insertions(+), 40 deletions(-)
 create mode 100644 python/langsmith/_internal/_compressed_runs.py

diff --git a/python/langsmith/_internal/_background_thread.py b/python/langsmith/_internal/_background_thread.py
index e595c5b73..ef83ac23f 100644
--- a/python/langsmith/_internal/_background_thread.py
+++ b/python/langsmith/_internal/_background_thread.py
@@ -17,8 +17,6 @@
     cast,
 )
 
-import zstandard as zstd
-
 from langsmith import schemas as ls_schemas
 from langsmith._internal._constants import (
     _AUTO_SCALE_DOWN_NEMPTY_TRIGGER,
@@ -100,10 +98,9 @@ def _tracing_thread_drain_queue(
 def _tracing_thread_drain_compressed_buffer(
     client: Client, size_limit: int = 100, size_limit_bytes: int | None = 20_971_520
 ) -> Optional[io.BytesIO]:
-    assert client.compressed_runs_buffer is not None
-    assert client.compressor_writer is not None
-    with client._buffer_lock:
-        current_size = client.compressed_runs_buffer.tell()
+    assert client.compressed_runs is not None
+    with client.compressed_runs.lock:
+        current_size = client.compressed_runs.buffer.tell()
 
         if size_limit is not None and size_limit <= 0:
             raise ValueError(f"size_limit must be positive; got {size_limit}")
@@ -113,21 +110,17 @@ def _tracing_thread_drain_compressed_buffer(
             )
 
         if (size_limit_bytes is None or current_size < size_limit_bytes) and (
-            size_limit is None or client._run_count < size_limit
+            size_limit is None or client.compressed_runs.run_count < size_limit
         ):
             return None
 
         # Write final boundary and close compression stream
-        client.compressor_writer.write(f"--{_BOUNDARY}--\r\n".encode())
-        client.compressor_writer.close()
+        client.compressed_runs.compressor_writer.write(f"--{_BOUNDARY}--\r\n".encode())
+        client.compressed_runs.compressor_writer.close()
 
-        filled_buffer = client.compressed_runs_buffer
+        filled_buffer = client.compressed_runs.buffer
 
-        client.compressed_runs_buffer = io.BytesIO()
-        client.compressor_writer = zstd.ZstdCompressor(
-            level=3, threads=-1
-        ).stream_writer(client.compressed_runs_buffer, closefd=False)
-        client._run_count = 0
+        client.compressed_runs.reset()
 
     filled_buffer.seek(0)
     return filled_buffer
diff --git a/python/langsmith/_internal/_compressed_runs.py b/python/langsmith/_internal/_compressed_runs.py
new file mode 100644
index 000000000..3fa0fba7d
--- /dev/null
+++ b/python/langsmith/_internal/_compressed_runs.py
@@ -0,0 +1,21 @@
+import io
+import threading
+
+import zstandard as zstd
+
+
+class CompressedRuns:
+    def __init__(self):
+        self.buffer = io.BytesIO()
+        self.run_count = 0
+        self.lock = threading.Lock()
+        self.compressor_writer = zstd.ZstdCompressor(level=3, threads=-1).stream_writer(
+            self.buffer, closefd=False
+        )
+
+    def reset(self):
+        self.buffer = io.BytesIO()
+        self.run_count = 0
+        self.compressor_writer = zstd.ZstdCompressor(level=3, threads=-1).stream_writer(
+            self.buffer, closefd=False
+        )
diff --git a/python/langsmith/client.py b/python/langsmith/client.py
index a273cf8e2..0fc2181f5 100644
--- a/python/langsmith/client.py
+++ b/python/langsmith/client.py
@@ -58,7 +58,6 @@
 from urllib import parse as urllib_parse
 
 import requests
-import zstandard as zstd
 from requests import adapters as requests_adapters
 from requests_toolbelt import (  # type: ignore[import-untyped]
     multipart as rqtb_multipart,
@@ -82,6 +81,7 @@
     tracing_control_thread_func_compress_parallel as _tracing_control_thread_func_compress_parallel,
 )
 from langsmith._internal._beta_decorator import warn_beta
+from langsmith._internal._compressed_runs import CompressedRuns
 from langsmith._internal._constants import (
     _AUTO_SCALE_UP_NTHREADS_LIMIT,
     _BLOCKSIZE_BYTES,
@@ -395,10 +395,7 @@ class Client:
         "_settings",
         "_manual_cleanup",
         "_pyo3_client",
-        "compressor_writer",
-        "_run_count",
-        "_buffer_lock",
-        "compressed_runs_buffer",
+        "compressed_runs",
         "_data_available_event",
         "_futures",
     ]
@@ -502,17 +499,12 @@ def __init__(
         # Create a session and register a finalizer to close it
         session_ = session if session else requests.Session()
         self.session = session_
-        if self.ls_utils.get_env_var("USE_RUN_COMPRESSION"):
+        if ls_utils.get_env_var("USE_RUN_COMPRESSION"):
             self._futures: set[cf.Future] = set()
-            self.compressed_runs_buffer: Optional[io.BytesIO] = io.BytesIO()
-            self.compressor_writer: zstd.ZstdCompressionWriter = zstd.ZstdCompressor(
-                level=3, threads=-1
-            ).stream_writer(self.compressed_runs_buffer, closefd=False)
-            self._buffer_lock: threading.Lock = threading.Lock()
+            self.compressed_runs: Optional[CompressedRuns] = CompressedRuns()
             self._data_available_event = threading.Event()
-            self._run_count: int = 0
         else:
-            self.compressed_runs_buffer = None
+            self.compressed_runs = None
 
         self._info = (
             info
@@ -522,7 +514,7 @@ def __init__(
         weakref.finalize(self, close_session, self.session)
         atexit.register(close_session, session_)
         # Initialize auto batching
-        if auto_batch_tracing and self.compressed_runs_buffer is not None:
+        if auto_batch_tracing and self.compressed_runs is not None:
             self.tracing_queue: Optional[PriorityQueue] = None
             threading.Thread(
                 target=_tracing_control_thread_func_compress_parallel,
@@ -1321,18 +1313,20 @@ def create_run(
         ):
             if self._pyo3_client is not None:
                 self._pyo3_client.create_run(run_create)
-            if self.compressed_runs_buffer is not None:
+            if self.compressed_runs is not None:
                 serialized_op = serialize_run_dict("post", run_create)
                 multipart_form = (
                     serialized_run_operation_to_multipart_parts_and_context(
                         serialized_op
                     )
                 )
-                with self._buffer_lock:
+                with self.compressed_runs.lock:
                     compress_multipart_parts_and_context(
-                        multipart_form, self.compressor_writer, _BOUNDARY
+                        multipart_form,
+                        self.compressed_runs.compressor_writer,
+                        _BOUNDARY,
                     )
-                    self._run_count += 1
+                    self.compressed_runs.run_count += 1
                     self._data_available_event.set()
             elif self.tracing_queue is not None:
                 serialized_op = serialize_run_dict("post", run_create)
@@ -1824,7 +1818,7 @@ def update_run(
         if attachments:
             data["attachments"] = attachments
         use_multipart = (
-            (self.tracing_queue is not None or self.compressed_runs_buffer is not None)
+            (self.tracing_queue is not None or self.compressed_runs is not None)
             # batch ingest requires trace_id and dotted_order to be set
             and data["trace_id"] is not None
             and data["dotted_order"] is not None
@@ -1852,17 +1846,19 @@ def update_run(
             self._pyo3_client.update_run(data)
         elif use_multipart:
             serialized_op = serialize_run_dict(operation="patch", payload=data)
-            if self.compressed_runs_buffer is not None:
+            if self.compressed_runs is not None:
                 multipart_form = (
                     serialized_run_operation_to_multipart_parts_and_context(
                         serialized_op
                     )
                 )
-                with self._buffer_lock:
+                with self.compressed_runs.lock:
                     compress_multipart_parts_and_context(
-                        multipart_form, self.compressor_writer, _BOUNDARY
+                        multipart_form,
+                        self.compressed_runs.compressor_writer,
+                        _BOUNDARY,
                     )
-                    self._run_count += 1
+                    self.compressed_runs.run_count += 1
                     self._data_available_event.set()
             elif self.tracing_queue is not None:
                 self.tracing_queue.put(
@@ -1889,7 +1885,7 @@ def _update_run(self, run_update: dict) -> None:
 
     def flush_compressed_runs(self, attempts: int = 3) -> None:
         """Force flush the currently buffered compressed runs."""
-        if self.compressed_runs_buffer is None:
+        if self.compressed_runs is None:
             return
 
         # Attempt to drain and send any remaining data
@@ -1926,7 +1922,7 @@ def flush_compressed_runs(self, attempts: int = 3) -> None:
 
     def flush(self) -> None:
         """Flush either queue or compressed buffer, depending on mode."""
-        if self.compressed_runs_buffer is not None:
+        if self.compressed_runs is not None:
             self.flush_compressed_runs()
         elif self.tracing_queue is not None:
             self.tracing_queue.join()

From 3ec9b6eec4e2544d00dfd7d1798f743ed1b1ab51 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 18:17:01 -0800
Subject: [PATCH 52/56] Make zstd optional

---
 .../langsmith/_internal/_compressed_runs.py   | 21 ++++++++++++++++---
 python/langsmith/_internal/_operations.py     | 10 +++++++--
 python/pyproject.toml                         |  4 +++-
 3 files changed, 29 insertions(+), 6 deletions(-)

diff --git a/python/langsmith/_internal/_compressed_runs.py b/python/langsmith/_internal/_compressed_runs.py
index 3fa0fba7d..3abda15d0 100644
--- a/python/langsmith/_internal/_compressed_runs.py
+++ b/python/langsmith/_internal/_compressed_runs.py
@@ -1,7 +1,12 @@
 import io
 import threading
 
-import zstandard as zstd
+try:
+    from zstandard import ZstdCompressor
+
+    HAVE_ZSTD = True
+except ImportError:
+    HAVE_ZSTD = False
 
 
 class CompressedRuns:
@@ -9,13 +14,23 @@ def __init__(self):
         self.buffer = io.BytesIO()
         self.run_count = 0
         self.lock = threading.Lock()
-        self.compressor_writer = zstd.ZstdCompressor(level=3, threads=-1).stream_writer(
+        if not HAVE_ZSTD:
+            raise ImportError(
+                "zstandard package required for compression. "
+                "Install with 'pip install langsmith[compression]'"
+            )
+        self.compressor_writer = ZstdCompressor(level=3, threads=-1).stream_writer(
             self.buffer, closefd=False
         )
 
     def reset(self):
         self.buffer = io.BytesIO()
         self.run_count = 0
-        self.compressor_writer = zstd.ZstdCompressor(level=3, threads=-1).stream_writer(
+        if not HAVE_ZSTD:
+            raise ImportError(
+                "zstandard package required for compression. "
+                "Install with 'pip install langsmith[compression]'"
+            )
+        self.compressor_writer = ZstdCompressor(level=3, threads=-1).stream_writer(
             self.buffer, closefd=False
         )
diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index 904a20d3b..23e2d2c1d 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -5,7 +5,13 @@
 import uuid
 from typing import Literal, Optional, Union, cast
 
-import zstandard as zstd
+try:
+    from zstandard import ZstdCompressionWriter
+except ImportError:
+
+    class ZstdCompressionWriter:  # type: ignore[no-redef]
+        """only used for typing checks."""
+
 
 from langsmith import schemas as ls_schemas
 from langsmith._internal import _orjson
@@ -277,7 +283,7 @@ def serialized_run_operation_to_multipart_parts_and_context(
 
 def compress_multipart_parts_and_context(
     parts_and_context: MultipartPartsAndContext,
-    compressor_writer: zstd.ZstdCompressionWriter,
+    compressor_writer: ZstdCompressionWriter,
     boundary: str,
 ) -> None:
     for part_name, (filename, data, content_type, headers) in parts_and_context.parts:
diff --git a/python/pyproject.toml b/python/pyproject.toml
index 05763c889..106e2a7b2 100644
--- a/python/pyproject.toml
+++ b/python/pyproject.toml
@@ -37,7 +37,8 @@ requests-toolbelt = "^1.0.0"
 
 # Enabled via `langsmith_pyo3` extra: `pip install langsmith[langsmith_pyo3]`.
 langsmith-pyo3 = { version = "^0.1.0rc2", optional = true }
-zstandard = "^0.23.0"
+# Enabled via `compression` extra: `pip install langsmith[compression]`.
+zstandard = { version = "^0.23.0", optional = true }
 
 [tool.poetry.group.dev.dependencies]
 pytest = "^7.3.1"
@@ -76,6 +77,7 @@ pytest-socket = "^0.7.0"
 [tool.poetry.extras]
 vcr = ["vcrpy"]
 langsmith_pyo3 = ["langsmith-pyo3"]
+compression = ["zstandard"]
 
 [build-system]
 requires = ["poetry-core"]

From f9aac67d39fb7f34691f975d24246b3433d18d87 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Thu, 19 Dec 2024 18:23:34 -0800
Subject: [PATCH 53/56] Make zstandard level configurable

---
 python/langsmith/_internal/_compressed_runs.py | 16 ++++++++++------
 1 file changed, 10 insertions(+), 6 deletions(-)

diff --git a/python/langsmith/_internal/_compressed_runs.py b/python/langsmith/_internal/_compressed_runs.py
index 3abda15d0..7871ebffc 100644
--- a/python/langsmith/_internal/_compressed_runs.py
+++ b/python/langsmith/_internal/_compressed_runs.py
@@ -8,6 +8,10 @@
 except ImportError:
     HAVE_ZSTD = False
 
+from langsmith import utils as ls_utils
+
+compression_level = ls_utils.get_env_var("RUN_COMPRESSION_LEVEL", 3)
+
 
 class CompressedRuns:
     def __init__(self):
@@ -19,9 +23,9 @@ def __init__(self):
                 "zstandard package required for compression. "
                 "Install with 'pip install langsmith[compression]'"
             )
-        self.compressor_writer = ZstdCompressor(level=3, threads=-1).stream_writer(
-            self.buffer, closefd=False
-        )
+        self.compressor_writer = ZstdCompressor(
+            level=compression_level, threads=-1
+        ).stream_writer(self.buffer, closefd=False)
 
     def reset(self):
         self.buffer = io.BytesIO()
@@ -31,6 +35,6 @@ def reset(self):
                 "zstandard package required for compression. "
                 "Install with 'pip install langsmith[compression]'"
             )
-        self.compressor_writer = ZstdCompressor(level=3, threads=-1).stream_writer(
-            self.buffer, closefd=False
-        )
+        self.compressor_writer = ZstdCompressor(
+            level=compression_level, threads=-1
+        ).stream_writer(self.buffer, closefd=False)

From 2ac7a3556310374ea5d1816a890b9f23b4bb837d Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Fri, 20 Dec 2024 11:50:12 -0500
Subject: [PATCH 54/56] mypy ignore optional imports

---
 python/langsmith/_internal/_compressed_runs.py | 2 +-
 python/langsmith/_internal/_operations.py      | 2 +-
 2 files changed, 2 insertions(+), 2 deletions(-)

diff --git a/python/langsmith/_internal/_compressed_runs.py b/python/langsmith/_internal/_compressed_runs.py
index 7871ebffc..2b838f3f1 100644
--- a/python/langsmith/_internal/_compressed_runs.py
+++ b/python/langsmith/_internal/_compressed_runs.py
@@ -2,7 +2,7 @@
 import threading
 
 try:
-    from zstandard import ZstdCompressor
+    from zstandard import ZstdCompressor # type: ignore[import]
 
     HAVE_ZSTD = True
 except ImportError:
diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index 23e2d2c1d..5393c3222 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -6,7 +6,7 @@
 from typing import Literal, Optional, Union, cast
 
 try:
-    from zstandard import ZstdCompressionWriter
+    from zstandard import ZstdCompressionWriter # type: ignore[import]
 except ImportError:
 
     class ZstdCompressionWriter:  # type: ignore[no-redef]

From 3b291c3f54502edd5775128ef72ca3d31f34202c Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Fri, 20 Dec 2024 11:51:01 -0500
Subject: [PATCH 55/56] lint

---
 python/langsmith/_internal/_compressed_runs.py | 2 +-
 python/langsmith/_internal/_operations.py      | 2 +-
 2 files changed, 2 insertions(+), 2 deletions(-)

diff --git a/python/langsmith/_internal/_compressed_runs.py b/python/langsmith/_internal/_compressed_runs.py
index 2b838f3f1..a30fbb7a1 100644
--- a/python/langsmith/_internal/_compressed_runs.py
+++ b/python/langsmith/_internal/_compressed_runs.py
@@ -2,7 +2,7 @@
 import threading
 
 try:
-    from zstandard import ZstdCompressor # type: ignore[import]
+    from zstandard import ZstdCompressor  # type: ignore[import]
 
     HAVE_ZSTD = True
 except ImportError:
diff --git a/python/langsmith/_internal/_operations.py b/python/langsmith/_internal/_operations.py
index 5393c3222..8f9771804 100644
--- a/python/langsmith/_internal/_operations.py
+++ b/python/langsmith/_internal/_operations.py
@@ -6,7 +6,7 @@
 from typing import Literal, Optional, Union, cast
 
 try:
-    from zstandard import ZstdCompressionWriter # type: ignore[import]
+    from zstandard import ZstdCompressionWriter  # type: ignore[import]
 except ImportError:
 
     class ZstdCompressionWriter:  # type: ignore[no-redef]

From c64fb92f65bb369028621048709334bbe4dadc47 Mon Sep 17 00:00:00 2001
From: Angus Jelinek <angus@langchain.dev>
Date: Fri, 20 Dec 2024 12:46:47 -0500
Subject: [PATCH 56/56] poetry lock

---
 python/poetry.lock | 9 +++++----
 1 file changed, 5 insertions(+), 4 deletions(-)

diff --git a/python/poetry.lock b/python/poetry.lock
index de2ec943d..a31c97af7 100644
--- a/python/poetry.lock
+++ b/python/poetry.lock
@@ -113,7 +113,7 @@ files = [
 name = "cffi"
 version = "1.17.1"
 description = "Foreign Function Interface for Python calling C code."
-optional = false
+optional = true
 python-versions = ">=3.8"
 files = [
     {file = "cffi-1.17.1-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:df8b1c11f177bc2313ec4b2d46baec87a5f3e71fc8b45dab2ee7cae86d9aba14"},
@@ -1280,7 +1280,7 @@ files = [
 name = "pycparser"
 version = "2.22"
 description = "C parser in Python"
-optional = false
+optional = true
 python-versions = ">=3.8"
 files = [
     {file = "pycparser-2.22-py3-none-any.whl", hash = "sha256:c3702b6d3dd8c7abc1afa565d7e63d53a1d0bd86cdc24edd75470f4de499cfcc"},
@@ -2200,7 +2200,7 @@ propcache = ">=0.2.0"
 name = "zstandard"
 version = "0.23.0"
 description = "Zstandard bindings for Python"
-optional = false
+optional = true
 python-versions = ">=3.8"
 files = [
     {file = "zstandard-0.23.0-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:bf0a05b6059c0528477fba9054d09179beb63744355cab9f38059548fedd46a9"},
@@ -2309,10 +2309,11 @@ cffi = {version = ">=1.11", markers = "platform_python_implementation == \"PyPy\
 cffi = ["cffi (>=1.11)"]
 
 [extras]
+compression = ["zstandard"]
 langsmith-pyo3 = ["langsmith-pyo3"]
 vcr = []
 
 [metadata]
 lock-version = "2.0"
 python-versions = ">=3.9,<4.0"
-content-hash = "7b8c702e50f6ae0f5a81bd2da1d6e0277f7fd28c5d02b2d62571573d3ae9f358"
+content-hash = "19b288e10f9d6c040798efb74ae2778103abdc87c298b8c3eb21f7685db56642"