Merge branch 'master' into cc/summarization_patch

# Conflicts:
#	libs/langchain_v1/langchain/agents/middleware/summarization.py

libs/langchain_v1/langchain/agents/middleware/summarization.py

@@ -3,7 +3,7 @@
 import uuid
 import warnings
 from collections.abc import Callable, Iterable, Mapping
-from functools import partial
+from functools import cache, partial
 from typing import Any, Literal, cast
 
 from langchain_core.messages import (
@@ -356,6 +356,10 @@ class SummarizationMiddleware(AgentMiddleware):
         if not messages:
             return 0
 
+        @cache
+        def suffix_token_count(start_index: int) -> int:
+            return self.token_counter(messages[start_index:])
+
         kind, value = self.keep
         if kind == "fraction":
             max_input_tokens = self._get_profile_limits()
@@ -370,7 +374,7 @@ class SummarizationMiddleware(AgentMiddleware):
         if target_token_count <= 0:
             target_token_count = 1
 
-        if self.token_counter(messages) <= target_token_count:
+        if suffix_token_count(0) <= target_token_count:
             return 0
 
         # Use binary search to identify the earliest message index that keeps the
@@ -383,7 +387,7 @@ class SummarizationMiddleware(AgentMiddleware):
                 break
 
             mid = (left + right) // 2
-            if self.token_counter(messages[mid:]) <= target_token_count:
+            if suffix_token_count(mid) <= target_token_count:
                 cutoff_candidate = mid
                 right = mid
             else:
@@ -397,8 +401,11 @@ class SummarizationMiddleware(AgentMiddleware):
                 return 0
             cutoff_candidate = len(messages) - 1
 
-        for i in range(cutoff_candidate, -1, -1):
-            if self._is_safe_cutoff_point(messages, i):
+        for i in range(cutoff_candidate, len(messages) + 1):
+            if (
+                self._is_safe_cutoff_point(messages, i)
+                and suffix_token_count(i) <= target_token_count
+            ):
                 return i
 
         return 0

libs/langchain_v1/tests/unit_tests/agents/middleware/implementations/test_summarization.py

@@ -1,10 +1,17 @@
-from typing import TYPE_CHECKING
+from typing import Iterable
 from unittest.mock import patch
 
 import pytest
 from langchain_core.language_models import ModelProfile
 from langchain_core.language_models.chat_models import BaseChatModel
-from langchain_core.messages import AIMessage, AnyMessage, HumanMessage, RemoveMessage, ToolMessage
+from langchain_core.messages import (
+    AIMessage,
+    AnyMessage,
+    HumanMessage,
+    MessageLikeRepresentation,
+    RemoveMessage,
+    ToolMessage,
+)
 from langchain_core.outputs import ChatGeneration, ChatResult
 from langgraph.graph.message import REMOVE_ALL_MESSAGES
 
@@ -316,7 +323,7 @@ def test_summarization_middleware_profile_inference_triggers_summary() -> None:
 
 
 def test_summarization_middleware_token_retention_pct_respects_tool_pairs() -> None:
-    """Ensure token retention keeps pairs together even if exceeding target tokens."""
+    """Ensure token retention never splits tool pairs while enforcing hard caps."""
 
     def token_counter(messages: list[AnyMessage]) -> int:
         return sum(len(getattr(message, "content", "")) for message in messages)
@@ -344,13 +351,13 @@ def test_summarization_middleware_token_retention_pct_respects_tool_pairs() -> N
     assert result is not None
 
     preserved_messages = result["messages"][2:]
-    assert preserved_messages == messages[1:]
+    assert preserved_messages == messages[3:]
+    assert token_counter(preserved_messages) <= 500
+    assert not any(isinstance(msg, (AIMessage, ToolMessage)) for msg in preserved_messages)
 
-    target_token_count = int(1000 * 0.5)
     preserved_tokens = middleware.token_counter(preserved_messages)
-
-    # Tool pair retention can exceed the target token count but should keep the pair intact.
-    assert preserved_tokens > target_token_count
+    target_token_count = int(1000 * 0.5)
+    assert preserved_tokens <= target_token_count
 
 
 def test_summarization_middleware_missing_profile() -> None:
@@ -783,6 +790,45 @@ def test_summarization_middleware_tool_call_in_search_range() -> None:
     assert middleware._is_safe_cutoff_point(messages, 1)
 
 
+def test_summarization_middleware_results_under_window() -> None:
+    """Ensure automatic profile inference triggers summarization when limits are exceeded."""
+
+    def _token_counter(messages: Iterable[MessageLikeRepresentation]) -> int:
+        count = 0
+        for message in messages:
+            if isinstance(message, ToolMessage):
+                count = count + 500
+            else:
+                count = count + 100
+        return count
+
+    state = {
+        "messages": [
+            HumanMessage(content="Message 1"),
+            AIMessage(
+                content="Message 2",
+                tool_calls=[
+                    {"name": "test", "args": {}, "id": "call-1"},
+                    {"name": "test", "args": {}, "id": "call-2"},
+                ],
+            ),
+            ToolMessage(content="Result 2-1", tool_call_id="call-1"),
+            ToolMessage(content="Result 2-2", tool_call_id="call-2"),
+        ]
+    }
+
+    middleware = SummarizationMiddleware(
+        model=ProfileChatModel(),
+        trigger=("fraction", 0.80),
+        keep=("fraction", 0.5),
+        token_counter=_token_counter,
+    )
+    result = middleware.before_model(state, None)
+    assert result is not None
+    count_after_summarization = _token_counter(result["messages"])
+    assert count_after_summarization <= 1000  # max_input_tokens of ProfileChatModel
+
+
 def test_summarization_middleware_zero_and_negative_target_tokens() -> None:
     """Test handling of edge cases with target token calculations."""
     # Test with very small fraction that rounds to zero